Potassium Carbonate → HCID 25171866, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 36 mg of potassium carbonate in methanol (3 ml) was added 37 mg of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(7S)-1,4-oxazepan-7-ylmethyl]benzamide (INTERMEDIATE 20) followed by 1-(bromomethyl)-3-(trifluoromethyl)benzene (13 μl). The mixture was heated to 70° C. and stirred for 8 h, and then cooled and added directly to a 40M samplet for purification via column chromatography on a Biotage Horizon 40M column, eluting with 1 column volume of 100% hexanes, followed by a gradient of 0 to 100% ethyl acetate in hexanes over 10 column volumes, followed by 4 column volumes of 100% ethyl acetate, to provide the title compound (28 mg, 56%). Mass spectrum (ESI) 577.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.33 (d, J=8.4 Hz, 2H), 7.96 (d, J=6.0 Hz, 2H), 7.94 (s, 1H), 7.61 (s, 1H), 7.52 (m, 3H), 7.44 (t, J=7.5 Hz, 1H), 6.65 (bs, 1H), 3.96 (m, 2H), 3.81 (m, 2H), 3.70 (s, 2H), 3.68 (m, 2H), 3.48 (sept, J=7.0 Hz, 1H), 3.25 (m, 1H), 2.74 (m, 2H), 2.01 (m, 1H), 1.82 (m, 1H), 1.46 (d, J=7.0 Hz, 6H).

Provenance & Evidence