5-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid → 5-amino-N-(5-((4S,5S)-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 297 as a pale brown solid (424 mg, 72% over 2 steps). 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 8.39 (dt, J=4.6, 1.4 Hz, 1H), 7.86 (s, 1H), 7.52 (ddd, J=10.8, 8.3, 1.4 Hz, 1H), 7.32-7.26 (m, 1H), 6.32 (s, 2H), 4.51 (dtd, J=47.9, 8.5, 3.6 Hz, 1H), 3.73 (s, 3H), 3.40-3.17 (m, 5H), 2.34-2.19 (m, 1H), 2.16-1.96 (m, 2H), 1.79-1.66 (m, 1H). Alkyl NH2 not seen. LCMS (ES+) m/z 449 (M+1)

Provenance & Evidence