Dimethylformamide → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)-3-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203076Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:13]([CH3:19])[C:12]=3[CH:20]=2)[C:4](=[O:21])[CH:3]=1.[F:22][C:23]([F:32])([F:31])[C:24]1[S:28][CH:27]=[C:26]([CH2:29][OH:30])[CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH:16]1([C:14]2[N:13]([CH3:19])[C:12]3[CH:20]=[C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:30][CH2:29][C:26]5[CH:25]=[C:24]([C:23]([F:32])([F:22])[F:31])[S:28][CH:27]=5)=[CH:3][C:4]4=[O:21])[CH:9]=[CH:10][C:11]=3[N:15]=2)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (800 mg), (5-(trifluoromethyl)-3-thienyl)methanol (972 mg), cesium carbonate (2.61 g) and DMF (8 ml) was stirred at 80° C. overnight. The mixture was poured into water and extracted with EtOAc-THF. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH-water to give the title compound (258 mg) as a white solid.

Workup

extractionextracted with EtOAc-THF
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by NH silica gel column chromatography (hexane/EtOAc)
customThe resulting solid was recrystallized from EtOH-water

Sources & evidence

ORD record: ord-2b9781243ef74d459beab5c4bf15ecd5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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