Hydrochloric Acid → HCID 67521942, compound

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:36])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[CH:32][CH:31]=[CH:30][C:29]=5[CH3:35])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:38].[ClH:40].CCOCC>>[ClH:38].[ClH:40].[ClH:38].[CH3:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:28]=1[CH:27]=[N:26][C:25]([C:23]1[C:22]([NH2:36])=[N:21][CH:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:18]=3)[CH:24]=1)=[CH:34]2

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 3283Diethyl Ether

HCID 6344Dichloromethane

HCID 675210244-{4-[6-Amino-5-(8-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67521942HCID 67521942, compound

Procedure

To a solution of 4-{4-[6-amino-5-(8-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (11.0 mg, 0.0227 mmol) in DCM (0.40 mL, 6.2 mmol) was added 1.0 M of HCl in Et2O (0.60 mL, 0.60 mmol), and the mixture was stirred at ambient temperature for 2 h. Almost immediately an off-white solid precipitated. The solvents were evaporated, and the residue was suspended in Et2O, filtered off, and dried in vacuo overnight, yielding the title compound as yellow solid. It appeared to be hygroscopic during the filtration; however, after the washing and initial drying it appeared to be non-hygroscopic. 1H NMR (400 MHz, DMSO-d6): δ=14.6 (very brs, 1H), 9.60 (s, 1H), 9.18-9.07 (brm, 1H), 9.05-8.92 (brm, 1H), 8.88 (d, J=2.0 Hz, 1H, 8.86 (brs, 1H), 8.73 (s, 1H), 8.51 (s, 1H), 8.45 (d, J=2.0 Hz, 1H), 8.16 (d, J=0.4 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.81 (dd, J=8.4, 6.8 Hz, 1H), 7.61 (d, J=6.8 Hz, 1H), 4.58-4.49 (m, 1H), 3.40 (brd, J=12.4 Hz, 2H), 3.12 (brq, J=12.2 Hz, 2H), 2.83 (s, 3H), 2.30-2.12 (m, 4H). MS(ES+): m/z=385.21 (43) [MH+], 302.15 (100) [MH+-piperidine]. HPLC: tR=1.80 min (polar—5 min, ZQ2).