Hydrochloric Acid → 1-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochloride
Reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[N:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2.[ClH:32]>CO.CCOCC>[ClH:32].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[N:18]=[N:19][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one (34 mg, 0.081 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (65 μL, 0.081 mmol), and the resulting solution was stirred at ambient temperature for 3 h. The solution was diluted with Et2O (20 mL), and the resulting solids were collected by filtration to provide the title compound (20 mg, 55%) as a yellow powder: 288-294° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.72 (d, J=9.0 Hz, 1H), 8.47 (d, J=8.5 Hz, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.41 (d, J=2.0 Hz, 1H), 7.23 (dd, J=7.5, 2.0 Hz, 1H), 4.19 (s, 2H), 3.72 (s, 3H), 3.38 (t, J=5.5 Hz, 2H), 3.00 (t, J=5.5 Hz, 2H); ESI MS m/z 427 [M+H]+; HPLC (Method A)>99% (AUC), tR=12.5 min.
Workup
- filtrationthe resulting solids were collected by filtration
Sources & evidence
- ORD record
- ord-a33651be8aa047208d9b83b1d77c52cb
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993765B2
Reaction notes
Loading…