Hydrochloric Acid → HCID 58358062, compound
Reaction equation
[Na].CO[C:4](=[O:37])[CH2:5][C:6]1=[N:7][N:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[C:9](=[O:29])/[C:10]/1=[C:11](/[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)\[CH2:12][C:13]1[CH:18]=[CH:17][C:16](OC)=[CH:15][CH:14]=1.Cl.C[CH:40]([OH:42])C>>[CH2:22]([N:21]1[C:4](=[O:37])[CH:5]=[C:6]2[NH:7][N:8]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[C:9](=[O:29])[C:10]2=[C:11]1[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([O:42][CH3:40])[CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=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-54921526525b479db59f2a4c2cd5a39d
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455485B2
Reaction notes
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