Benzoyl chloride → 1-Benzoyl-1,2,4,7-tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 1-methylethyl ester

HRID 1252992Notes

Reaction equation

HRID 1252992 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[N:5]([NH:23][C:24](=[O:26])[CH:25]=2)[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[C:27]([N:23]1[N:5]2[CH:6]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[C:7]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]2=[CH:25][C:24]1=[O:26])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 141304321,2,4,7-Tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimdine-6-carboxylic acid, 1-methylethyl ester

Product 1

HCID 141304341-Benzoyl-1,2,4,7-tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 1-methylethyl ester

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1,2,4,7-tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 1-methylethyl ester (36 mg; 0.1 mmole) in dichloromethane (2 ml) and pyridine (1 ml) under argon was treated with benzoyl chloride (28 mg; 0.2 mmole). The reaction was allowed to stir for 30 minutes and then diluted with ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, water, sodium bicarbonate and brine. It was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by preparative thin layer chromatography (40% acetone in hexanes) and the product was crystallized from absolute ethanol to provide a solid, melting point 201°-203° C.

Workup

  1. washThe resulting solution was washed with 1N hydrochloric acid, water, sodium bicarbonate and brine
  2. dry with materialIt was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by preparative thin layer chromatography (40% acetone in hexanes)
  5. customthe product was crystallized from absolute ethanol
  6. customto provide a solid, melting point 201°-203° C.

Sources & evidence

ORD record
ord-1f55c69efeed4bbdb5bf140c72cebad0
Source dataset
uspto-grants-1988_05
Patent number
US04746656

Reaction notes

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