Lansoprazole → 2-(2-Carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetamide

HRID 411621Notes

Reaction equation

HRID 411621 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.[C:33]([CH2:36][O:37][C:38]1[CH:39]=[C:40]([S:49](Cl)(=[O:51])=[O:50])[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C:46](=[O:48])[NH2:47])(=[O:35])[NH2:34]>C(#N)C>[C:33]([CH2:36][O:37][C:38]1[CH:39]=[C:40]([S:49]([N:21]2[C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=[C:17]2[S:15]([CH2:14][C:3]2[C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])[CH:6]=[CH:5][N:4]=2)=[O:16])(=[O:51])=[O:50])[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C:46]([NH2:47])=[O:48])(=[O:35])[NH2:34]

Participants

5

Reactant 3

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 185412373,4-Bis(carbamoylmethoxy)benzenesulfonyl chloride

Product 1

HCID 101534602-(2-Carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetamideYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (369.3 mg) was suspended in acetonitrile (10 ml)-triethylamine (2 ml) and 3,4-bis(carbamoylmethoxy)benzenesulfonyl chloride (340 mg) was added. The reaction mixture was stirred at room temperature overnight. Solids were filtered and washed with acetonitrile (10 ml) followed with acetone (5 ml). The solids were again resuspended in methanol (3 ml), filtered and dried in vacuo to give 2-(2-carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetamide (527 mg).

Workup

  1. additionwas added
  2. filtrationSolids were filtered
  3. washwashed with acetonitrile (10 ml)
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-380cce06d3984438be60c9bd8e685793
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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