Lansoprazole → 2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)-N-(2-pyridyl)acetamide

HRID 411615Notes

Reaction equation

HRID 411615 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[O:16])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].C(N(CC)CC)C.Cl[S:34]([C:37]1[CH:53]=[CH:52][C:40]([O:41][CH2:42][C:43]([NH:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)=[O:44])=[CH:39][CH:38]=1)(=[O:36])=[O:35]>ClCCl>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:17]2[N:18]([S:34]([C:37]3[CH:53]=[CH:52][C:40]([O:41][CH2:42][C:43]([NH:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=4)=[O:44])=[CH:39][CH:38]=3)(=[O:35])=[O:36])[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[O:16])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:11])[F:12]

Participants

5

Reactant 3

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 185412102-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

Product 1

HCID 102402872-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)-N-(2-pyridyl)acetamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[[ [3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (185 mg) dissolved in 20 ml of dichloromethane and 0.2 ml of triethylamine was added to 170 mg of 2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide. The reaction mixture was washed with water. Organic layer was dried over anhydrous magnesium sulfate, and evaporated. Residual material was lyophilized to give 237 mg of the titled product. M.P. 78-81° C.

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-dd0629f46eed412484a12a78cac02279
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

Loading…