Dichloromethane → HCID 57423902, compound

Participants

Reaction Steps

4-{4-[2-Oxo-6-(trifluoromethoxy)-2,3-dihydro-1H-benzimidazol-1-yl]piperidin-1-yl}tetrahydro-2H-pyran-4-carbonitrile (D36, 62 mg) in tetrahydrofuran (5 ml) was treated with 3M methylmagnesium bromide solution in tetrahydrofuran (0.3 ml) and stirred for 2 hours. A second aliquot of 3M methylmagnesium bromide solution in tetrahydrofuran (0.3 ml) was added and the solution was stirred for 2 hours, then treated with saturated ammonium chloride solution (3 ml). The mixture was treated with dichloromethane and water. The dichloromethane layer was separated, dried by passing through a 3 g hydromatrix cartridge and the solvent was removed. The residue was dissolved in methanol and treated with hydrogen chloride in ether to give a white solid which partitioned between dichloromethane and sodium bicarbonate solution. The dichloromethane layer was separated, dried by passing through a hydromatrix cartridge and the solvent was removed. The residue was treated with hydrogen chloride in ether to give the title compound as a white solid (28 mg). M+ 400.

Provenance & Evidence