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

Participants

Reaction Steps

Following the procedure for Example 107 starting from N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide and 5-(tert-butoxycarbonylamino)-2-(pyridin-2-yl)thiazole-4-carboxylic acid gave 387 as an off-white solid (106 mg, 68% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.54 (d, J=4.6 Hz, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.81 (s, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.29-7.20 (m, 1H), 6.27 (s, 2H), 4.90 (d, J=47.2 Hz, 1H), 3.73 (s, 3H), 3.58-3.33 (m, 3H), 3.23-3.11 (m, 2H), 2.44-2.22 (m, 1H), 2.11-1.92 (m, 2H), 1.87-1.76 (m, 1H). Exchangeable NH2 not observed. LCMS (ES+) m/z 431 (M+1)

Provenance & Evidence