Piperidine → N-[(1R,6S)-6-Amino-2,2-difluorocyclohexyl]-5-(difluoromethyl)-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxamide

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Reaction Steps

To a stirred solution of 9H-fluoren-9-ylmethyl[(1S,2R)-2-({[5-(difluoromethyl)-4-(imidazo[1,2-b]pyridazin-3-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (27 mg, 0.042 mmol) in DMF (0.8 mL) was added piperidine (0.08 mL, 0.83 mmol). The mixture was left to stir for 1 h, diluted with water, and extracted with EtOAc. The organic layer was dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.38 (s, 1H); 8.72 (d, 1H); 8.68 (dd, 1H); 8.43 (s, 1H); 8.27 (dd, 1H); 7.97 (s, 1H); 7.38 (dd, 1H); 7.35 (t, 1H); 4.05 (m, 1H); 2.82 (m, 1H); 1.30-2.10 (m, 6H). LRMS (APCI) calc'd for (C18H18F4N5OS) [M+H]+, 428.1. found 428.1.

Provenance & Evidence