Hydrochloric Acid → 1-H-indol-3-yl-N-[6-(1-methylpiperidin-4-ylcarbonyl)-pyridin-2-yl]-carboxamide dihydrochloride salt
Reaction equation
[ClH:1].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[O:21])[N:15]=2)=[O:12])=[CH:3]1>C(OCC)C>[ClH:1].[ClH:1].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[O:21])[N:15]=2)=[O:12])=[CH:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Add 2.0M HCl in diethylether (0.46 mL, 0.93 mmol) to a suspension of 1H-indol-3-yl-N-[6-(1-methylpiperidin-4-ylcarbonyl)-pyridin-2-yl]-carboxamide (free base) (0.16 g, 0.44 mmol) in diethylether (10 mL). After 2 hr. filter the reaction mixture and wash the solid with diethylether to afford the title compound as a yellow solid. Rf 0.29 (93:7:1 CHCl3/methanol/NH4OH); m.p. 200-218° C.; 1H NMR (CD3OD, complex mixture of rotamers) 8.38 and 8.49 (s, 1H), 8.46 (m, 1H), 8.08-8.10 and 8.18-8.29 (m, 2H), 7.61 and 7.72 (d, J=8 Hz, 1H), 7.52 (m, 1H), 7.26-7.32 (m, 2H), 4.01 (m, 1H), 3.19-3.68 (m, 3H), 2.97 (m, 1H), 2.82 and 2.94 (s, 3H), 2.28-2.32 (m, 2H), 1.68-2.02 (m, 2H); CIMS (Methane) m/z 363 [C21H22N4O2+H]+; HPLC (Method A) 96.7%, tR 16.4 min.; anal. calculated for C21H22N4O2.2.1HCl.1.5H2O: C, 54.12; H, 5.86; N, 12.02; Cl, 15.98. Found: C, 54.13; H, 6.03; N, 12.37; Cl, 15.71.
Workup
- filtrationfilter the reaction mixture
- washwash the solid with diethylether
Sources & evidence
- ORD record
- ord-e9e29839f4bc45e0820e51fc351f1a4c
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748459B2
Reaction notes
Loading…