Lansoprazole → HCID 10175513, compound

HRID 411619Notes

Reaction equation

HRID 411619 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:26]([CH2:29][NH:30][C:31](=[O:44])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1)(=[O:28])[NH2:27]>ClCCl.C(N(CC)CC)C>[C:26]([CH2:29][NH:30][C:31](=[O:44])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([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:41])=[O:42])=[CH:36][CH:35]=1)(=[O:28])[NH2:27]

Participants

5

Reactant 2

HCID 3883LansoprazoleHCID 18541183HCID 18541183, compound

Product 1

HCID 10175513HCID 10175513, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (185 mg) was dissolved in 20 ml of dichloromethane and 0.5 ml of triethylamine, and N-(carbamoylmethyl)-2-[4-(chlorosulfonyl)phenoxy]acetamide (158 mg) was added. The reaction mixture was stirred at room temperature for 24 hr. Dichloromethane (100 ml) was added to the reaction mixture. The reaction mixture was washed with saturated NaCl solution, and 0.1N sodium bicarbonate solution. Dichloromethane layer was separated and dried over anhydrous magnesium sulfate. Dichloromethane was evaporated under reduced pressure to give syrupy material, which was lyophilized in vacuo. 237 mg of the titled product was obtained.

Workup

  1. washThe reaction mixture was washed with saturated NaCl solution, and 0.1N sodium bicarbonate solution
  2. customDichloromethane layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customDichloromethane was evaporated under reduced pressure
  5. customto give syrupy material, which

Sources & evidence

ORD record
ord-0e76bfde48b3450ba03a7c50194a390a
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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