Sodium Methoxide → 2-Methoxy-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide

HRID 467961Notes

Reaction equation

HRID 467961 reaction equation
Br[C:2]1[N:3]([CH3:28])[CH:4]=[C:5]([C:7]([N:9]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)=[O:8])[N:6]=1.[CH3:29][O-:30].[Na+]>O1CCCC1>[CH3:29][O:30][C:2]1[N:3]([CH3:28])[CH:4]=[C:5]([C:7]([N:9]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 469166852-Bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide

Product 1

HCID 469167282-Methoxy-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamideYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide (100 mg), sodium methoxide (14 mg) and tetrahydrofuran (1 mL) was stirred at 60° C. for 3 days. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:1) and TLC (NH silica gel plate; hexane/ethyl acetate=1:1) to give the titled compound (6 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:1) and TLC (NH silica gel plate; hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-bb69695468f54ab4ae8efce05d3fe656
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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