Hydrochloric Acid → HCID 178469942, compound

HRID 1516572Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:14])[NH:8][N:9](C(=O)C)[CH:10]=1)=[O:5])[CH3:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 1-acetyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxilic acid ethyl ester (2.7 g, This compound was prepared in a similar manner to that described in Bioorganic & Medicinal Chemistry Letters (2002), 12 (16), 2105-2108), benzylbromide (2.5 g), potassium carbonate (2.1 g) in N,N-dimethylformamide (20 mL) was stirred at 40° C. for 20 hours. To this reaction mixture was added 1 mol/L hydrochloric acid, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (1.6 g).

Workup

customThis compound was prepared in a similar manner to that
extractionthis mixture was extracted with ethyl acetate
washThis organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-b3400d7581ef4008aa251344796047de
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

Loading…