Dimethylamine → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-({1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl}methyl)benzamide

Participants

Reaction Steps

A 5-ml microwave vial was charged with N-{[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (31 mg, EXAMPLE 7) and dimethylamine (2M in tetrahydrofuran, 3 ml). The resultant mixture was heated to 130° C. for 15 min in a microwave reactor. The mixture was concentrated in vacuo and the residue purified via flash chromatography on a Biotage Horizon 25M column, eluting with 10 column volumes of 100% ethyl acetate, to provide the title compound (15 mg, 48%). Mass spectrum (ESI) 524.3 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.2 Hz, 2H), 7.94 (m, 5H), 7.52 (s, 1H), 6.30 (t, J=5.8 Hz, 1H), 5.84 (d, J=6.0 Hz, 1H), 4.43 (d, J=10.8 Hz, 2H), 3.48 (sept, J=6.8 Hz, 1H), 3.45 (t, J=6.4 Hz, 2H), 3.13 (s, 3H), 2.84 (t, J=11.2 Hz, 2H), 1.93, (m, 3H), 1.46 (d, J=7.0 Hz, 6H), 1.37 (m, 2H).

Provenance & Evidence