Sodium hydride → HCID 25152050, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture was sodium hydride (9 mg, 60% dispersion) in 5 ml of dimethylformamide was added 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(5-methyl-2-oxo-1,3-oxazolidin-5-yl)methyl]benzamide (31 mg, EXAMPLE 65) followed by 2-chloro-4-trifluoromethylpyrimidine (14 mg). The mixture was stirred at 70° C. for 1 h. Excess sodium hydride was quenched by addition of 1 ml of methanol. The sample was then purified via mass-directed HPLC on a Kromasil C18 column eluting with a gradient of 10% acetonitrile in water (0.01% TFA) to 60% acetonitrile in water (0.01% TFA) providing the title compound (25 mg, 59%). Mass spectrum (ESI) 565.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.94 (d, J=3.9 Hz, 1H), 8.33 (d, J=7.8 Hz, 2H), 7.95 (s, 1H), 7.94 (d, J=7.3 Hz, 2H), 7.52 (s, 1H), 7.36 (d, J=4.1 Hz, 1H), 6.69 (bs, 1H), 4.26 (d, J=11.2 Hz, 1H), 4.12 (d, J=10.7 Hz, 1H), 3.99 (dd, J=14.6, 6.2 Hz, 1H), 3.55 (dd, J=14.8, 6.1 Hz, 1H), 3.48 (sept, J=6.5 Hz, 1H), 1.66 (s, 3H), 1.46 (d, J=6.7 Hz, 6H).

Provenance & Evidence