Phenyl isocyanate → HCID 57485446, compound

Participants

Reaction Steps

To a solution of compound 49 (0.060 g, 0.152 mmol) in anhydrous methylene chloride (1.52 mL) at room temperature under argon was added phenyl isocyanate (0.018 mL, 0.160 mmol). The reaction mixture was stirred at room temperature for 17 h and another portion of phenyl isocyanate (0.018 mL, 0.160 mmol) was added. After additional stirring at room temperature for 17 h, the reaction mixture was quenched with methanol (1.0 mL) and concentrated. Purification by silica gel chromatography (eluant: 100% methylene chloride to 100% EtOAc gradient) gave 32.7 mg (42% yield) of 5-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolyl]carbonylamino]-N-phenyl-1H-indazole-1-carboxamide (50) as a white solid. 1H NMR (500 MHz, CD3OD) δ 8.31 (br d, 1H, J=8.8 Hz), 8.24 (m, 2H), 7.70 (m, 3H), 7.39 (br t, 2H, J=7.9 Hz), 7.16 (t, 1H, J=7.4 Hz), 4.90 (br s, 2H), 4.20 (m, 2H), 3.08 (td, 1H, J=12.4, 3.1 Hz), 2.75 (dd, 1H, J=12.3, 12.6 Hz), 1.89 (m, 1H), 1.82 (m, 1H), 1.74 (m, 1H), 1.65 (m, 1H), 1.23 (m, 1H), 1.01 (d, 3H, J=6.6 Hz). MS (M+1): 513.

Provenance & Evidence