Methyl 3-amino-4-methylbenzoate → 4-methyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-benzoic acid methyl ester

HRID 491840Notes

Reaction equation

HRID 491840 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]=1[CH3:10])=[O:4].[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([NH2:27])[CH:21]=1>CCO>[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([NH:27][CH2:2][C:3]([C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9]=2[CH3:10])=[O:4])[CH:21]=1

Participants

4

Reactant 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 27764392-Bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)ethan-1-one

Product 1

HCID 588612934-methyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-benzoic acid methyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-ethanone (829 mg, 2.97 mmol) and 3-amino-4-methyl benzoic acid methyl ester in 6 mL of EtOH was stirred at 75° C. for 6 h. The mixture was cooled, and the resulting precipitate was filtered and washed with cold EtOH to provide 564 mg (1.55 mmol, 52%) of 4-methyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-benzoic acid methyl ester as a white powder.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with cold EtOH

Sources & evidence

ORD record
ord-b4763fb919a0420686463381d4980f48
Source dataset
uspto-grants-2009_05
Patent number
US07531560B2

Reaction notes

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