Lansoprazole → HCID 59769506, compound

HRID 874124Notes

Reaction equation

HRID 874124 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([C:14](Cl)=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[CH3:17][C:18]1[C:19]([CH2:30][S:31]([C:33]2[NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[N:34]=2)=[O:32])=[N:20][CH:21]=[CH:22][C:23]=1[O:24][CH2:25][C:26]([F:29])([F:28])[F:27].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]([C:14]([N:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[S:31]([CH2:30][C:19]1[C:18]([CH3:17])=[C:23]([O:24][CH2:25][C:26]([F:27])([F:28])[F:29])[CH:22]=[CH:21][N:20]=1)=[O:32])=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 85900220HCID 85900220, compound

Product 1

HCID 59769506HCID 59769506, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution (10 mL) of 2-[(chlorocarbonyl)(phenyl)amino]ethyl acetate (0.58 g) prepared in the same manner as in Synthetic Example 25 in tetrahydrofuran were added 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (0.739 g), triethylamine (0.558 mL) and 4-dimethylaminopyridine (0.024 g), and the mixture was stirred at 60° C. for 15 hrs. Ethyl acetate (30 mL) was added to the reaction mixture, and the mixture was washed with water (50 mL) and saturated brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (eluted with acetone:hexane=1:4, then 3:2). Crystallization from diethyl ether gave the title compound (0.779 g) as a white solid.

Workup

  1. washthe mixture was washed with water (50 mL) and saturated brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash silica gel column chromatography (
  5. washeluted with acetone
  6. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-dd9e53546775421686881e42d4a84074
Source dataset
uspto-grants-2015_03
Patent number
US08980322B2

Reaction notes

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