CAS 102625-64-9

5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole

Codes: S-pantoprazole sodium-018

Application context (from source-drug indications)

Gastro-oesophageal reflux diseaseS-pantoprazole sodiumPeptic ulcerS-pantoprazole sodiumHaemorrhageS-pantoprazole sodiumTrauma and injuryS-pantoprazole sodiumComaS-pantoprazole sodiumAspiration pneumoniaS-pantoprazole sodium

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
S-pantoprazole sodium	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.

S-pantoprazole sodiumOptimised routesteps: 8total yield: 2.5g(Pantoprazole (Free))

4-Acetamidophenol→Chlorodifluoromethane→N-[4-(Difluoromethoxy)phenyl]acetamide→N-[4-(Difluoromethoxy)-2-nitrophenyl]acetamide→2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→4-(Difluoromethoxy)-2-nitroaniline→1,2-Diamino-4-(difluoromethoxy)benzene→O-Ethylxanthic acid potassium salt→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→(3,4-Dimethoxypyridin-2-yl)methanol

S-pantoprazole sodiumOptimised routesteps: 11total yield: 5.2g((S)-(-)-Pantoprazole sodium (API))

3-Hydroxy-2-methyl-4H-pyran-4-one→3-Methoxy-2-methyl-4H-pyran-4-one→3-Methoxy-2-methylpyridin-4-one→4-Chloro-3-methoxy-2-methylpyridine→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→4-Chloro-3-methoxy-2-methylpyridine 1-oxide→3,4-Dimethoxy-2-methylpyridine 1-oxide→(3,4-Dimethoxypyridin-2-yl)methanol→2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfinyl)-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 2total yield: 209g((S)-(-)-Pantoprazole sodium (API))

5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfinyl)-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 6total yield: /

4-Acetamidophenol→Chlorodifluoromethane→N-[4-(Difluoromethoxy)phenyl]acetamide→N-[4-(Difluoromethoxy)-2-nitrophenyl]acetamide→N-[2-Amino-4-(difluoromethoxy)phenyl]acetamide→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 1total yield: /

5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→(+)-5-(Difluoromethoxy)-2-[(R)-[(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 4total yield: 7g(Pantoprazole (Free))

2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→Aminothiocarboxamide→(3,4-Dimethoxypyridin-2-yl)methyl hydrosulfide→Chloridocarbonic acid ethyl ester→Ethyl (3,4-dimethoxy-2-pyridyl)methylsulfanylformate→1,2-Diamino-4-(difluoromethoxy)benzene→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfinyl)-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 3total yield: 2.83g(Pantoprazole (Free))

4-(Difluoromethoxy)-2-nitroaniline→1,2-Diamino-4-(difluoromethoxy)benzene→Carbon disulfide→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→2-(chloromethyl)-3,4-dimethoxypyridine→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→2-(Chloromethyl)-3,4-dimethoxy-1-oxo-1lambda5-pyridine→S-pantoprazole sodium-061

S-pantoprazole sodiumOptimised routesteps: 6total yield: 65g(Pantoprazole (Free))

3-methoxy-2-methyl-4-nitro-1-oxido-1-pyridin-1-ylium→(3-methoxy-4-nitropyridin-2-yl)methyl methanesulfonate→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→4-Chloro-3-methoxy-2-methylpyridine 1-oxide→(4-chloro-3-methoxypyridin-2-yl)methyl methanesulfonate→2-[[(4-Chloro-3-methoxypyridin-2-yl)methyl]sulfanyl]-5-(difluoromethoxy)-1H-benzimidazole

S-pantoprazole sodiumOptimised routesteps: 1total yield: /

5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole

S-pantoprazole sodiumProcess routesteps: 7total yield: 1.1kg((S)-(-)-Pantoprazole sodium (API))

2-(Chloromethyl)-3,4-dimethoxypyridine hydrogen chloride→5-(Difluoromethoxy)-1H-benzimidazole-2-thiol→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→(-)-(S)-Pantoprazole

S-pantoprazole sodiumOptimised routesteps: 5total yield: 54.1g((S)-(-)-Pantoprazole sodium (API))

5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfanyl)-1H-benzimidazole→5-(Difluoromethoxy)-2-(3,4-dimethoxypyridin-2-ylmethylsulfinyl)-1H-benzimidazole→1-[5-(Difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-benzimidazol-1-yl]ethan-1-one→1-[5-(Difluoromethoxy)-2-[(S)-(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-benzimidazol-1-yl]ethan-1-one→(-)-(S)-Pantoprazole

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