4-Formylbenzoic acid → HCID 18441949, compound

HRID 458411Notes

Reaction equation

HRID 458411 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([OH:15])=[O:14].Cl.[NH2:25][C:26]1[N:30]2[CH2:31][CH2:32][CH2:33][N:29]2[C:28](=[O:34])[CH:27]=1.CC[O-].[Na+]>CCO.O>[CH2:8]([O:7][C:5]([C:4]1[CH:20]([C:19]2[CH:22]=[CH:23][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)[C:27]2[C:28](=[O:34])[N:29]3[CH2:33][CH2:32][CH2:31][N:30]3[C:26]=2[NH:25][C:3]=1[C:2]([F:12])([F:11])[F:1])=[O:6])[CH3:9]

Participants

7

Reactant 4

HCID 120884-Formylbenzoic acidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2723922Sodium ethoxideHCID 674357713-Amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one--hydrogen chloride (1/1)

Product 1

HCID 18441949HCID 18441949, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 4,4,4-trifluoroacetoacetate (0.3 mL, 2.05 mmol), 4-carboxybenzaldehyde (300 mg, 2.00 mmol), 3-amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one hydrochloride (refs. R. B. Greenwald, U.S. Pat. No. 4,128,425, and E. E. Boros, F. Bouvier, S. Randhawa and M. H. Rabinowitz, J. Heterocyclic Chem., 2001, 38, 613–616.) (˜350 mg, 2.00 mmol) and NaOEt (170 mg, 2.5 mmol) in EtOH (5 mL) was heated at reflux for 24 h. The reaction mixture was diluted with water and the resulting precipitate was collected by filtration. The filter cake was triturated with EtOAc to afford the title compound as a white solid (460 mg, 1.05 mmol, 51% crude): 1H NMR (400 MHz, DMSO-d6) δ 12.79 (br s, 1H), 10.19 (s, 1H), 7.83 (d, 2H, J=8), 7.25 (d, 2H, J=8), 4.78 (s, 1H), 3.92 (q, 2H, J=7), 3.40 (m, 4H), 2.30 (m, 2H), 0.98 (t, 3H, J=7) ppm; ESI-MS m/z 436 (M−H)−;

Workup

  1. temperatureat reflux for 24 h
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe filter cake was triturated with EtOAc

Sources & evidence

ORD record
ord-b14c8c3f1c594f41a69b54ff26c39637
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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