Methylamine → HCID 22177258, compound

Participants

Reaction Steps

A mixture of 2-(3′-cyano-biphenyl-4-yl)-N-(3,5-dichloro-phenyl)-4oxo-butyramide (300 mg, 0.71 mmol) and MeNH2 (2M in THF, 1.77 mL, 3.54 mmol, 5 eq) in 1,2-dichloroethane (3.5 mL) was stirred at r.t. for 1 h and then Na(AcO)3BH (299 mg, 1.4 mmol, 2 eq) was added. The reaction mixture was stirred at r.t. for 16 h. The mixture was then partitioned between EtOAc (20 mL) and 10% NaHCO3 (10 mL) and the organic phase separated. The organic phase was washed with 10% NaHCO3 (10 mL×2), saturated brine (10 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (Et3N/MeOH/CH2Cl2 1:10:90) gave 56.5 mg (18%) of the title compound as a yellowish gum. 1H NMR (300 MHz, CDCl3): δ 7.89 (m, 2H), 7.72 (m, 1H), 7.61 (m, 7H), 7.14 (t, 1H), 4.04 (dd, 1H), 2.85 (t, 2H), 2.59 (s, 3H), 2.50 (m, 1H), 2.16 (m, 1H). MS(ESI): 438.0 (M+1), 440.0 (M+3).

Provenance & Evidence