Sodium hydride → HCID 178510093, compound

Participants

Reaction Steps

To a mixture of 115 mg (0.43 mmol) of trans-(4-Cyclobutyl-piperazin-1-yl)-(4-hydroxy-cyclohexyl)-methanone (Intermediate 3) in 1 ml of N,N-dimethylacetamide (DMA), 19 mg (0.44 mmol) of sodium hydride was added at room temperature and stirred for 30 min. To the mixture, 100 mg (0.72 mmol) of 6-chloronicotinonitrile (commercially available) was added and stirred at 160° C. for 14 h. The mixture was poured into saturated NaHCO3 solution., extracted with AcOEt. The organic layer was washed with water and brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography on silica eluting with CH2Cl2 and methanol=from 98:2 to 95:5. The combined product fractions were evaporated to dryness to yield 30 mg (11%) of the title compound. MS (m/e): 369.2 (MH+).

Provenance & Evidence