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CAS 139481-44-0

methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

Codes: AZILS-004, AZIL-007

Application context (from source-drug indications)

HypertensionAzilsartanEssential hypertensionAzilsartanType 2 diabetesAzilsartanObesityAzilsartanDiabetesAzilsartanHypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneEssential hypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneEssential hypertensionAzilsartan Medoxomil PotassiumHypertensionAzilsartan Medoxomil Potassium

Source drugs (routes using this intermediate)

DrugTierExpiry
AzilsartanTier C — Watch / trade-
Azilsartan Medoxomil Potassium/ChlorthalidoneTier C — Watch / trade-
Azilsartan Medoxomil PotassiumTier 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.

AzilsartanOriginator routesteps: 6total yield: 0.135 g
AzilsartanOptimised routesteps: 2total yield: 7.5 g
methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→2,6-dichloro-9-((3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purine
Azilsartan Medoxomil Potassium/ChlorthalidoneOptimised routesteps: 6total yield: 2.55 kg
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
Azilsartan Medoxomil PotassiumOptimised routesteps: 6total yield: 2.55 kg
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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