Hydrochloric Acid → HCID 58358062, compound
Reaction equation
[Na].[CH2:2]([NH:9]/[C:10](=[C:20]1\[C:21]([CH2:33][C:34]([O:36]C)=O)=[N:22][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:24]\1=[O:25])/[CH2:11][C:12]1[CH:17]=[CH:16][C:15](OC)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C[CH:40]([OH:42])C>>[CH2:2]([N:9]1[C:34](=[O:36])[CH:33]=[C:21]2[NH:22][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[C:24](=[O:25])[C:20]2=[C:10]1[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([O:42][CH3:40])[CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
Procedure
An isopropanolic solution of i-PrONa, obtained by dissolving of sodium (0.017 g, 0.75 mmol, 2 equiv.) in i-PrOH (2 ml), was treated with methyl [(4E)-4-[1-(benzylamino)-2-(4-methoxyphenyl)ethylidene]-1-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) (170 mg, 0.36 mmol, 1 equiv.). The reaction mixture was stirred at room temperature for 0.5 h, then cooled and neutralized to pH 6 by addition 1M HCl solution. i-PrOH were removed in vacuo and the crude was purified by flash chromatography to yield 24 mg of pure product 5-benzyl-2-(2-chlorophenyl)-4-(3-methoxybenzyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione. Yield 14%. 1HNMR (500 MHz, DMSO-d6): 3.69 (s, 3H); 4.40-4.60 (m, 2H); 5.08-5.24 (m, 2H), 5.72 (s, 1H); 6.71-6.73 (m, 2H), 6.80-6.82 (m, 1H); 7.02-7.03 (m, 2H); 7.21-7.25 (m, 3H); 7.28-7.31 (m, 3H); 7.47-7.49 (m, 2H); 7.62-7.66 (m, 2H). MS (ESI+): 472.9; MS (ESI−): 470.7.
Workup
- temperaturecooled
- customi-PrOH were removed in vacuo
- customthe crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-f729f2c146ae4397ab9d5e999c0c3d38
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012449B2
Reaction notes
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