Benzylamine → HCID 68456803, compound

Participants

Reaction Steps

4-Hydroxy-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (120 mg, 0.37 mmol) and benzylamine (0.3 mL) were irradiated in a microwave tube for min at 300 W. Purification by column chromatography (12 g ISCO column eluting with ethyl acetate and a methanol/ammonia mixture (10:1); gradient 100% ethyl acetate to 80% ethyl acetate over 30 min at 25 mL/min) provided the free-base. This was converted to the dihydrochloride as in Example 64 to provide the title compound (43 mg, 22%) as a yellow solid: mp 180-185° C.; 1H NMR (500 MHz, CD3OD) δ 8.25 (s, 1H), 7.90 (d, J=1.8 Hz, 1H), 7.87 (d, J=8.9 Hz, 1H), 7.75 (s, 1H), 7.51-7.49 (dd, J=8.9, 1.9 Hz, 1H), 7.40-7.39 (m, 4H), 7.33-7.30 (dd, J=8.5, 4.3 Hz, 1H), 6.63 (d, J=76 Hz, 1H), 4.90 (t, J=5.9 Hz, 2H), 4.54 (s, 2H), 3.86 (t, J=5.9 Hz, 2H), 3.77-3.68 (m, 2H), 3.18-3.13 (m, 2H), 2.17-2.13 (m, 2H), 2.03-2.00 (m, 2H); ESI MS m/z 414 [M+H]+; HPLC (Method C)>99% (AUC), tR=12.9 min.

Provenance & Evidence