Diisopropylethylamine → HCID 25152047, compound

Participants

Reaction Steps

To a solution of N-{[3-(5-aminopyridin-2-yl)-5-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (10 mg, INTERMEDIATE 23) and diisopropylethylamine (7 μl) in 4 ml of dichloromethane was added picolinoyl chloride (3 mg). The mixture was stirred at room temperature for 1 h. The sample was purified directly via column chromatography on a Biotage Horizon 12M column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 4 column volumes to provide the title compound (4 mg, 34%). Mass spectrum (ESI) 616.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 9.01 (s, 1H), 8.69 (d, J=3.9 Hz, 1H), 8.47 (d, J=8.4 Hz, 2H), 8.33 (d, J=8.3 Hz, 2H), 8.31 (d, J=7.8 Hz, 1H), 8.16 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.92 (s, 1H), 7.73 (s, 1H), 7.51 (s, 1H), 7.41 (bs, 1H), 6.65 (bs, 1H), 4.94 (bs, 1H), 4.04 (d, J=10.3 Hz, 1H), 3.99 (dd, J=14.2, 6.6 Hz, 1H), 3.83 (dd, J=14.4, 6.4 Hz, 1H), 3.47 (sept, J=7.0 Hz, 1H), 1.67 (s, 3H), 1.46 (d, J=6.9 Hz, 6H).

Provenance & Evidence