3,5-Dimethylisoxazole-4-boronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(3,5-dimethylisoxazol-4-yl)thiazole-4-carboxamide

Participants

Reaction Steps

Following the procedure for Example 101 starting from tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate (Intermediate 99), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (3,5-dimethylisoxazol-4-yl)boronic acid gave 234. 1H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 8.47 (s, 1H), 7.78 (s, 1H), 4.82 (dd, J=10.8, 3.6 Hz, 1H), 4.56-4.32 (m, 1H), 4.25-3.93 (m, 2H), 3.79 (s, 3H), 3.27-3.13 (m, 1H), 2.74 (s, 3H), 2.53 (s, 3H), 2.13-2.01 (m, 1H), 1.93-1.78 (m, 1H), 1.77-1.64 (m, 2H). LCMS (ES+) m/z 435 (M+1).

Provenance & Evidence