Hydrochloric Acid → HCID 46182772, compound

HRID 1471438Notes

Reaction equation

HRID 1471438 reaction equation
[Na].[CH2:2]([NH:9]/[C:10](=[C:18]1/[C:19]([CH2:31][C:32]([O:34]C)=O)=[N:20][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:22]/1=[O:23])/[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CC(O)C>[CH2:2]([N:9]1[C:32](=[O:34])[CH:31]=[C:19]2[NH:20][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:22](=[O:23])[C:18]2=[C:10]1[CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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 (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-3b4349f6b28e40ab91fbbee57888f8d7
Source dataset
uspto-grants-2015_04
Patent number
US09012449B2

Reaction notes

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