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CAS 80841-78-7
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one
Codes: OLME-009, AZIL-011
Application context (from source-drug indications)
HypertensionOlmesartan Medoxomil/Amlodipine MaleateHypertensionOlmesartan Medoxomil/Amlodipine orotateHypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneEssential hypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneHypertensionOlmesartan Medoxomil/AzelnidipineEssential hypertensionAmlodipine Besylate/Olmesartan MedoxomilHypertensionAmlodipine Besylate/Olmesartan MedoxomilHypertensionOlmesartan MedoxomilIschaemic strokeOlmesartan MedoxomilHeart failureOlmesartan MedoxomilMetabolic syndromeOlmesartan MedoxomilGlomerulonephritisOlmesartan MedoxomilType 2 diabetesOlmesartan MedoxomilEssential hypertensionAzilsartan Medoxomil PotassiumHypertensionAzilsartan Medoxomil Potassium
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Olmesartan Medoxomil/Amlodipine Maleate | Tier C — Watch / trade | - |
| Olmesartan Medoxomil/Amlodipine orotate | Tier C — Watch / trade | - |
| Azilsartan Medoxomil Potassium/Chlorthalidone | Tier C — Watch / trade | - |
| Olmesartan Medoxomil/Azelnidipine | Tier C — Watch / trade | - |
| Amlodipine Besylate/Olmesartan Medoxomil | Tier C — Watch / trade | - |
| Olmesartan Medoxomil | Tier B — Position early | - |
| Azilsartan Medoxomil Potassium | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
(2R,3R,4R,5S)-2-((benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate→1,1,1-trimethoxybutane→2-propyl-1H-imidazole-4,5-dicarbonitrile→diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→lithium 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→ethyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→1-bromo-4-(bromomethyl)benzene→ethyl 1-(4-bromobenzyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→(2-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)phenyl)boronic acid→ethyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbonitrile→4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-6-ol→4'-((6-hydroxy-4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
(2R,3R,4R,5S)-2-((benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate→1,1,1-trimethoxybutane→2-propyl-1H-imidazole-4,5-dicarbonitrile→diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→lithium 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→ethyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→1-bromo-4-(bromomethyl)benzene→ethyl 1-(4-bromobenzyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→(2-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)phenyl)boronic acid→ethyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbonitrile→4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-6-ol→4'-((6-hydroxy-4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
3-nitrophthalic acid→2-(methoxycarbonyl)-6-nitrobenzoic acid→methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate→methyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate→methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→methyl 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→N'-hydroxy-4'-methyl-[1,1'-biphenyl]-2-carboximidamide hydrochloride→N'-((ethoxycarbonyl)oxy)-4'-methyl-[1,1'-biphenyl]-2-carboximidamide→3-(4'-methyl-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one→tert-butyl 3-(4'-methyl-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→tert-butyl 3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→tert-butyl 3-(4'-((2-ethoxy-7-(methoxycarbonyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→1-((2'-(4-(tert-butoxycarbonyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid→tert-butyl 3-(4'-((2-ethoxy-7-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy)carbonyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate
methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-nitrophenyl carbonochloridate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-(((4-nitrophenoxy)carbonyl)oxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid→sodium (Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→bis(2,5-dioxopyrrolidin-1-yl) carbonate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
(2R,3R,4R,5S)-2-((benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate→1,1,1-trimethoxybutane→2-propyl-1H-imidazole-4,5-dicarbonitrile→diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→lithium 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→ethyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→1-bromo-4-(bromomethyl)benzene→ethyl 1-(4-bromobenzyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→(2-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)phenyl)boronic acid→ethyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbonitrile→4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-6-ol→4'-((6-hydroxy-4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
(2R,3R,4R,5S)-2-((benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate→1,1,1-trimethoxybutane→2-propyl-1H-imidazole-4,5-dicarbonitrile→diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→lithium 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→ethyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→1-bromo-4-(bromomethyl)benzene→ethyl 1-(4-bromobenzyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→(2-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)phenyl)boronic acid→ethyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbonitrile→4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-6-ol→4'-((6-hydroxy-4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
(2R,3R,4R,5S)-2-((benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate→1,1,1-trimethoxybutane→2-propyl-1H-imidazole-4,5-dicarbonitrile→diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→lithium 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate→ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→ethyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→1-bromo-4-(bromomethyl)benzene→ethyl 1-(4-bromobenzyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate→(2-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)phenyl)boronic acid→ethyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate→4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-1-((2'-(1-(2-phenylpropan-2-yl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-propyl-1H-imidazole-5-carboxylate
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbonitrile→4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-6-ol→4'-((6-hydroxy-4,4-dimethyl-2-propyl-4,6-dihydro-1H-furo[3,4-d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
3-nitrophthalic acid→2-(methoxycarbonyl)-6-nitrobenzoic acid→methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→methyl 2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate→methyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate→methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→methyl 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one
4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→N'-hydroxy-4'-methyl-[1,1'-biphenyl]-2-carboximidamide hydrochloride→N'-((ethoxycarbonyl)oxy)-4'-methyl-[1,1'-biphenyl]-2-carboximidamide→3-(4'-methyl-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one→tert-butyl 3-(4'-methyl-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→tert-butyl 3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→tert-butyl 3-(4'-((2-ethoxy-7-(methoxycarbonyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate→1-((2'-(4-(tert-butoxycarbonyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid→tert-butyl 3-(4'-((2-ethoxy-7-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy)carbonyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-yl)-5-oxo-1,2,4-oxadiazole-4(5H)-carboxylate
methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-nitrophenyl carbonochloridate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-(((4-nitrophenoxy)carbonyl)oxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→4-(chloromethyl)-5-methyl-1,3-dioxol-2-one→(Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid→sodium (Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→bis(2,5-dioxopyrrolidin-1-yl) carbonate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-(trityloxy)carbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate→(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
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