Hydrochloric Acid → HCID 68459372, compound

Participants

Reaction Steps

(E)-4-(4-Fluorostyryl)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (70 mg, 0.16 mmol), and ammonium formate (20.7 mg, 0.328 mmol) were stirred in methanol (4 ml) for 5 min. Palladium on carbon (100 mg) was added, and the mixture was heated to reflux for 1.5 h. The reaction mixture was cooled to room temperature, filtered through celite, rinsed with ethanol, and then concentrated. The residue was dissolved in methanol (2 mL) and treated with 1 equivalent of 2 M HCl in Et2O and the mixture was concentrated to provide the title compound (39.4 mg, 9.1%) as a yellow solid: mp 55-60° C.; 1H NMR (500 MHz, CD3OD) δ 8.23 (s, 1H), 7.84-7.75 (m, 2H), 7.60-7.54 (dd, J=6.7, 0.6 Hz, 1H), 7.47-7.41 (dd, J=8.9, 2.0 Hz, 1H), 7.28-7.20 (m, 2H), 7.04-6.96 (m, 2H), 6.47-6.40 (m, 2H), 4.87 (t, J=5.7 Hz, 2H), 3.86 (t, J=5.7 Hz, 2H), 3.74-3.63 (br m, 2H), 3.21-3.10 (br m, 2H), 3.01-2.92 (m, 2H), 2.92-2.83 (m, 2H), 2.23-2.09 (m, 2H), 2.08-1.95 (m, 2H); ESI MS m/z 431 [M+H]+; HPLC (Method D) 92.5% (AUC), tR=12.9 min.

Provenance & Evidence