5-((Tert-butoxycarbonyl)amino)-2-(2,5-difluorophenyl)thiazole-4-carboxylic acid → 5-amino-N-(5-((4S,5R)-4-amino-5-fluoroazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2,5-difluorophenyl)thiazole-4-carboxamide

Participants

Reaction Steps

Following the procedure for Example 221 starting from N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide and 5-(tert-butoxycarbonyl-amino)-2-(2,5-difluorophenyl)thiazole-4-carboxylic acid gave 295 as a dark cream solid (166 mg, 73% over three steps. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.87-7.81 (m, 2H), 7.17-7.09 (m, 1H), 7.07-7.01 (m, 1H), 6.16 (s, 2H), 4.90 (dd, J=47.1, 6.7 Hz, 1H), 3.74 (s, 3H), 3.49-3.32 (m, 3H), 3.23-3.09 (m, 2H), 2.36-2.28 (m, 1H), 2.18-1.81 (m, 3H). Alkyl NH2 not seen. LCMS (ES+) m/z 466 (M+1)

Provenance & Evidence