N-(1-(4-amino-1-cyclopropyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide → 5-amino-N-(5-((4S,5S)-4-amino-5-fluoroazepan-1-yl)-1-cyclopropyl-1H-pyrazol-4-yl)-2-(2-fluoro-5-methylphenyl)thiazole-4-carboxamide

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Reaction Steps

Following the procedure for Example 107 starting from N-(1-(4-amino-1-cyclopropyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide and 5-(tert-butoxycarbonyl-amino)-2-(2-fluoro-5-methylphenyl)thiazole-4-carboxylic acid gave 277 as a yellow solid (228 mg, 55% over two steps). 1H NMR (400 MHz, d4-MeOD) δ 8.07 (dd, J=7.3, 2.3 Hz, 1H), 7.48 (s, 1H), 7.24-7.19 (m, 1H), 7.11 (dd, J=11.4, 8.4 Hz, 1H), 4.49 (dtd, J=48.3, 8.8, 3.8 Hz, 1H), 3.56-3.48 (m, 1H), 3.47-3.34 (m, 4H), 3.23-3.13 (m, 1H), 2.41 (s, 3H), 2.35-2.21 (m, 1H), 2.19-2.06 (m, 1H), 2.01-1.91 (m, 1H), 1.84-1.72 (m, 1H), 1.19-1.10 (m, 2H), 1.11-1.04 (m, 2H). LCMS (ES+) m/z 488 (M+1)

Provenance & Evidence