1,3-Dimethylpyrazole-4-boronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(1,3-dimethyl-1H-pyrazol-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 (1,3-dimethyl-1H-pyrazol-4-yl)boronic acid gave 241. 1H NMR (400 MHz, DMSO-d6) δ 9.63 (s, 1H), 8.28 (s, 1H), 8.24 (s, 1H), 7.84 (s, 1H), 4.95-4.83 (m, 1H), 4.83-4.62 (m, 1H), 4.42-4.28 (m, 1H), 4.24-4.05 (m, 1H), 3.83 (s, 3H), 3.78 (s, 3H), 3.48 (dd, J=17.3, 8.4 Hz, 1H), 2.47 (s, 3H), 2.15-2.06 (m, 1H), 1.87 (d, J=14.4 Hz, 4H). LCMS (ES+) m/z 434 (M+1).

Provenance & Evidence