5-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-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-(3-fluoropyridin-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-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid gave 388 as an off-white solid (120 mg, 74% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 8.42 (s, 1H), 7.85 (t, J=9.8 Hz, 1H), 7.64 (s, 1H), 7.50-7.44 (m, 1H), 4.85 (d, J=47.3 Hz, 1H), 3.64 (s, 3H), 3.40-3.22 (m, 3H), 3.23-2.83 (m, 2H), 2.31-2.01 (m, 1H), 2.04-1.66 (m, 2H), 1.92-1.48 (m, 1H). Exchangeable NH2 (×2) and NH not observed. LCMS (ES+) m/z 449 (M+1)

Provenance & Evidence