Sodium hydride → HCID 25171238, compound

Participants

Reaction Steps

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(piperidin-4-ylmethyl)benzamide (25 mg, INTERMEDIATE 15) in tetrahydrofuran (5 ml) was added sodium hydride (5 mg of a 60% dispersion in oil). The reaction was allowed to stir at room temperature for five min, and then 1-(bromomethyl)-4-(trifluoromethyl)benzene was added. The reaction was stirred for 1 h and then was concentrated. The residue was purified by reverse-phase HPLC on a Biotage Parallex Flex, Kromasil C18 21×100 mm column, eluting at 15 ml/min with 90% water (0.1% TFA) to 95% acetonitrile (0.1% TFA) over 10 min, hold for 2 min, then back to 90% water over 0.5 min, hold for 0.5 min, to provide the title compound (5 mg, 14.4%). Mass spectrum (ESI) 561.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.31 (d, J=8.5 Hz, 2H), 7.92-7.94 (m, 3H), 7.55 (d, J=8 Hz, 2H), 7.50 (s, 1H), 7.42 (d, J=8 Hz, 2H), 6.37 (m, 1H), 3.54 (s, 2H), 3.44-3.51 (m, 2H), 3.40 (m, 2H), 2.89 (m, 2H), 1.98-2.03 (m, 2H), 1.83 (s, 1H) 1.74-1.77 (m, 2H), 1.67-1.71 (m, 1H), 1.45 (d, J=7 Hz, 6H), 1.36-1.40 (m, 2H), 1.25 (m, 1H).

Provenance & Evidence