3-Methyl-2-pyridineboronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(3-methylpyridin-2-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-methylpyridin-2-yl)boronic acid gave 231. 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.53 (dd, J=4.7, 1.5 Hz, 1H), 8.47 (s, 1H), 7.91-7.83 (m, 1H), 7.81 (s, 1H), 7.45 (dd, J=7.7, 4.6 Hz, 1H), 4.84 (dd, J=10.7, 3.6 Hz, 1H), 4.53-4.30 (m, 1H), 4.25-3.94 (m, 2H), 3.79 (s, 3H), 3.29-3.12 (m, 1H), 2.85 (s, 3H), 2.51 (s, 1H), 2.13-2.02 (m, 1H), 1.94-1.79 (m, 1H), 1.76-1.62 (m, 4H). LCMS (ES+) m/z 431 (M+1).

Provenance & Evidence