2,3,6-Trifluorophenylboronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2,3,6-trifluorophenyl)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 (2,3,6-trifluorophenyl)boronic acid gave 243. 1H NMR (400 MHz, DMSO-d6) δ 9.93 (s, 1H), 8.67 (s, 1H), 7.83 (s, 1H), 7.73 (qd, J=9.5, 5.0 Hz, 1H), 7.38 (tdd, J=9.5, 3.9, 2.1 Hz, 1H), 4.83 (dd, J=10.7, 3.6 Hz, 1H), 4.45-4.23 (m, 1H), 4.17 (ddd, J=21.9, 15.0, 1.8 Hz, 1H), 4.08-3.89 (m, 1H), 3.77 (s, 3H), 3.29-3.13 (m, 1H), 2.12-2.01 (m, 1H), 1.87-1.72 (m, 1H), 1.72-1.60 (m, 4H). LCMS (ES+) m/z 470 (M+1).

Provenance & Evidence