Hydrochloric Acid → HCID 46182772, compound

HRID 1253445Notes

Reaction equation

HRID 1253445 reaction equation
[Na].C[O:3][C:4](=O)[CH2:5][C:6]1=[N:7][N:8]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:9](=[O:27])/[C:10]/1=[C:11](\[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.Cl>CC(O)C>[CH2:20]([N:19]1[C:4](=[O:3])[CH:5]=[C:6]2[NH:7][N:8]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:9](=[O:27])[C:10]2=[C:11]1[CH2:12][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 178499639HCID 178499639, compound

Product 1

HCID 46182772HCID 46182772, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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[(4Z)-4-[1-(benzylamino)-2-morpholin-4-ylethylidene]-1-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate tate (Compound of Formula (XIV) (170 mg, 0.75 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 9 mg of pure product 5-benzyl-2-(2-chlorophenyl)-4-(morpholin-4-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione. Yield 12%. 1HNMR (500 MHz, DMSO-d6): 2.37-2.41 (m, 4H); 3.94-4.00 (m, 2H); 5.52-5.55 (m, 2H), 5.84 (s, 1H); 7.07-7.09 (m, 2H), 7.22-7.28 (m, 2H); 7.30-7.33 (m, 2H); 7.48-7.51 (m, 2H); 7.59-7.61 (m, 1H); 7.63-7.67 (m, 1H). MS (ESI+): 451.9; MS (ESI−): 449.7.

Workup

  1. temperaturecooled
  2. customi-PrOH were removed in vacuo
  3. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-5f7cf8536bf84e038cc346193e2173cd
Source dataset
uspto-grants-2013_06
Patent number
US08455485B2

Reaction notes

Loading…