(S)-Rabeprazole sodium → 2-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)-N-(2-pyridyl)acetamide

HRID 411618Notes

Reaction equation

HRID 411618 reaction equation
Cl[S:2]([C:5]1[CH:21]=[CH:20][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Na].[CH3:23][O:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH2:35][S:36]([C:38]2[NH:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[N:39]=2)=[O:37])[C:30]=1[CH3:47]>ClCCl.C(N(CC)CC)C>[CH3:23][O:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH2:35][S:36]([C:38]2[N:39]([S:2]([C:5]3[CH:21]=[CH:20][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=4)=[O:12])=[CH:7][CH:6]=3)(=[O:4])=[O:3])[C:40]3[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=3[N:42]=2)=[O:37])[C:30]=1[CH3:47]

Participants

5

Reactant 2

HCID 9821387(S)-Rabeprazole sodiumHCID 185412102-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

Product 1

HCID 103124822-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)-N-(2-pyridyl)acetamideYield 75.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

170 mg of 2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide was added to 191 mg of 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole sodium salt in dichloromethane (15 ml) and triethylamine (0.1 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water. Organic layer was dried over anhydrous magnesium sulfate, and evaporated. Residual material was lyophilized in vacuo to give 244 mg of the titled product.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialOrganic layer was dried over anhydrous magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-8404a06165e149758b64e446a958f1e0
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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