Hydrochloric Acid → HCID 68458293, compound

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].C(OCC)C>C(Cl)Cl>[ClH:33].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

A solution of (R)-4-(benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (10.5 mg, 0.024 mmol) in CH2Cl2 (0.3 mL) was treated with anhydrous HCl in diethyl ether (24 μL, 0.024 mmol, 1.0 M). After stirring at ambient temperature for 2.0 h, the reaction mixture was concentrated, dissolved in CH3CN and H2O, partially concentrated, and then lyophilized to yield the title compound (11.9 mg, quantitative) as an off white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.58 (br s, 0.5H), 8.24 (s, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.48-7.36 (m, 6H), 6.12 (dd, J=8.0, 3.0 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.53-5.39 (m, 1H), 5.15 (s, 2H), 4.87 (s, 2H), 3.88-3.51 (m, 5H), 3.21-3.16 (m, 1H), 2.15-2.08 (m, 1H), 1.30-1.23 (m, 1H); ESI MS m/z 433 [M+H]+, HPLC (Method A)>99.0% (AUC), tR=14.1 min.