Ethyl benzoylacetate → HCID 178468555, compound

HRID 270925Notes

Reaction equation

HRID 270925 reaction equation
C(O[C:4](=[O:14])[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[CH2:15]([O:17][C:18]([C:20]1[NH:21][N:22]=[C:23]([NH2:25])[CH:24]=1)=[O:19])[CH3:16]>C(O)(=O)C>[CH2:15]([O:17][C:18]([C:20]1[CH:24]=[C:23]2[NH:25][C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:5][C:4](=[O:14])[N:22]2[N:21]=1)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 4321844ethyl 5-amino-1H-pyrazole-3-carboxylate

Product 1

HCID 178468555HCID 178468555, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.56 mL (3.22 mmol) of 3-oxo-3-phenyl-propionic acid ethyl ester and 0.50 g (3.22 mmol) 5-amino-2H-pyrazole-3-carboxylic acid ethyl ester in 4 mL of acetic acid (HOAc) was heated at reflux for 4 h, during which time a precipitate formed. The precipitate was filtered off, washed with ethyl acetate and dried to give 0.51 g (56% yield) of 7-oxo-5-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid ethyl ester as a solid as indicated by 1H NMR; LC-MS—calcd for C15H13N3O3 [M++H]+: 284.1, found: 284.1.

Workup

  1. temperatureat reflux for 4 h, during which time a precipitate
  2. customformed
  3. filtrationThe precipitate was filtered off
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-c2d04d38a443436cb347aab0dec054db
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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