Ammonia → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

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Reaction Steps

A solution of tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (100 mg, 0.19 mmol) and TFA (2 mL) in DCM (4 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure to afford a residue. The residue was diluted with MeOH (10 mL), neutralized with 28% ammonia solution, concentrated, and purified by preparative HPLC to afford 145 as a white solid (45 mg, 56%). 1H-NMR (500 MHz, CD3OD) δ (ppm) 9.03 (s, 1H), 8.71 (d, J=6.5 Hz, 1H), 8.36 (s, 1H), 8.28 (s, 1H), 7.98 (s, 1H), 7.65-7.68 (m, 1H), 7.25 (d, J=7.5 Hz, 1H), 6.58 (d, J=8.5 Hz, 1H), 3.90-3.94 (m, 4H), 3.14-3.16 (m, 2H), 2.91-2.94 (m, 2H), 2.05-2.10 (m, 2H), 1.68 (s, 9H); MS (ESI) m/z: 417 [M+H]+.

Provenance & Evidence