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CAS 114772-53-1

4'-methyl-[1,1'-biphenyl]-2-carbonitrile

Codes: TELM-028, FIMA-014, IRBE-009, AZILS-018, AZIL-023

Application context (from source-drug indications)

HypertensionTelmisartan/Amlodipine Besylate/HydrochlorothiazideEssential hypertensionAmlodipine Besylate/Fimasartan PotassiumHypertensionAmlodipine Besylate/Fimasartan PotassiumHypertensionRosuvastatin Calcium/TelmisartanHyperlipidaemiaRosuvastatin Calcium/TelmisartanHypertensionAtorvastatin Calcium Hydrate/IrbesartanHyperlipidaemiaAtorvastatin Calcium Hydrate/IrbesartanHypertensionIrbesartan/TrichlormethiazideHypertensionAzilsartanEssential hypertensionAzilsartanType 2 diabetesAzilsartanObesityAzilsartanDiabetesAzilsartanHypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneEssential hypertensionAzilsartan Medoxomil Potassium/ChlorthalidoneHypertensionAmlodipine Besylate/TelmisartanHypertensionTelmisartanBreast cancerTelmisartanCardiomyopathyTelmisartanAlzheimer's diseaseTelmisartanRisk-reduction measureTelmisartanMyocardial infarctionTelmisartanOesophageal diseaseIrbesartanHypertensionIrbesartanDiabetic nephropathyIrbesartanHypercholesterolaemiaIrbesartanAlbuminuriaIrbesartanType 2 diabetesIrbesartanHypertensionFimasartan Potassium TrihydrateEssential hypertensionFimasartan Potassium TrihydrateHypercholesterolaemiaFimasartan Potassium TrihydrateChronic renal impairmentFimasartan Potassium TrihydrateRenal impairmentFimasartan Potassium TrihydrateHepatic function declineFimasartan Potassium TrihydrateEssential hypertensionAzilsartan Medoxomil PotassiumHypertensionAzilsartan Medoxomil Potassium

Source drugs (routes using this intermediate)

DrugTierExpiry
Telmisartan/Amlodipine Besylate/HydrochlorothiazideTier C — Watch / trade-
Amlodipine Besylate/Fimasartan PotassiumTier C — Watch / trade-
Rosuvastatin Calcium/TelmisartanTier C — Watch / trade-
Atorvastatin Calcium Hydrate/IrbesartanTier C — Watch / trade-
Irbesartan/TrichlormethiazideTier C — Watch / trade-
AzilsartanTier C — Watch / trade-
Azilsartan Medoxomil Potassium/ChlorthalidoneTier C — Watch / trade-
Amlodipine Besylate/TelmisartanTier C — Watch / trade-
TelmisartanTier B — Position early-
IrbesartanTier B — Position early-
Fimasartan Potassium TrihydrateTier 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.

Telmisartan/Amlodipine Besylate/HydrochlorothiazideOptimised routesteps: 4total yield: 0.20 g
1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbaldehyde→4'-((1,7'-dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carbaldehyde
Amlodipine Besylate/Fimasartan PotassiumOptimised routesteps: 3total yield: /
5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→5-(4'-methyl-[1,1'-biphenyl]-2-yl)-1H-tetrazole→5-(4'-methyl-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole
Rosuvastatin Calcium/TelmisartanOptimised routesteps: 4total yield: 0.20 g
1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbaldehyde→4'-((1,7'-dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carbaldehyde
Atorvastatin Calcium Hydrate/IrbesartanOriginator routesteps: 6total yield: 1.42 g
ethyl 1-aminocyclopentane-1-carboxylate→ethyl pentanimidate→2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→2-(2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole→p-tolylmagnesium bromide→4,4-dimethyl-2-(4'-methyl-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile
Irbesartan/TrichlormethiazideOriginator routesteps: 6total yield: 1.42 g
ethyl 1-aminocyclopentane-1-carboxylate→ethyl pentanimidate→2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→2-(2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole→p-tolylmagnesium bromide→4,4-dimethyl-2-(4'-methyl-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile
AzilsartanOptimised routesteps: 5total yield: 13.5 g
4'-methyl-[1,1'-biphenyl]-2-carbonitrile→2,6-dichloro-9-((3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purine→3-(4'-methyl-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one→3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one→2,6-dichloro-9-((3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purine→ethyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate→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→2,6-dichloro-9-((3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purine→ethyl 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→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→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: 5total yield: /
4'-methyl-[1,1'-biphenyl]-2-carbonitrile→N'-hydroxy-4'-methyl-[1,1'-biphenyl]-2-carboximidamide→3-(4'-methyl-[1,1'-biphenyl]-2-yl)-5-(trichloromethyl)-1,2,4-oxadiazole→3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-5-(trichloromethyl)-1,2,4-oxadiazole→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: 9total yield: 26.2 g
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
Amlodipine Besylate/TelmisartanOptimised routesteps: 4total yield: 0.20 g
1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbaldehyde→4'-((1,7'-dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carbaldehyde
TelmisartanOptimised routesteps: 4total yield: 0.20 g
1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbaldehyde→4'-((1,7'-dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carbaldehyde
IrbesartanOriginator routesteps: 6total yield: 1.42 g
ethyl 1-aminocyclopentane-1-carboxylate→ethyl pentanimidate→2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one→4'-(bromomethyl)-[1,1'-biphenyl]-2-carbonitrile→4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile→2-(2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole→p-tolylmagnesium bromide→4,4-dimethyl-2-(4'-methyl-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile
Fimasartan Potassium TrihydrateOptimised routesteps: 3total yield: /
5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole→4'-methyl-[1,1'-biphenyl]-2-carbonitrile→5-(4'-methyl-[1,1'-biphenyl]-2-yl)-1H-tetrazole→5-(4'-methyl-[1,1'-biphenyl]-2-yl)-1-trityl-1H-tetrazole
Azilsartan Medoxomil PotassiumOptimised routesteps: 5total yield: /
4'-methyl-[1,1'-biphenyl]-2-carbonitrile→N'-hydroxy-4'-methyl-[1,1'-biphenyl]-2-carboximidamide→3-(4'-methyl-[1,1'-biphenyl]-2-yl)-5-(trichloromethyl)-1,2,4-oxadiazole→3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-5-(trichloromethyl)-1,2,4-oxadiazole→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 PotassiumOptimised routesteps: 9total yield: 26.2 g
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

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