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

Participants

Reaction Steps

Following the procedure for Example 101 starting from tert-butyl ((3R,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate (Intermediate 100), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (5-fluoropyridin-3-yl)boronic acid gave 246. 1H NMR (400 MHz, DMSO-d6) δ 10.01 (s, 1H), 9.13 (t, J=1.7 Hz, 1H), 8.76 (d, J=2.8 Hz, 1H), 8.55 (s, 1H), 8.40-8.32 (m, 1H), 7.72 (s, 1H), 5.05-4.73 (m, 2H), 4.21-4.05 (m, 1H), 4.05-3.91 (m, 1H), 3.79 (s, 3H), 3.29-3.24 (m, 1H), 2.21-2.10 (m, 1H), 1.94-1.77 (m, 2H), 1.71-1.61 (m, 1H). LCMS (ES+) m/z 435 (M+1).

Provenance & Evidence