Hydrochloric Acid → HCID 68409423, compound

HRID 2194705Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:7]1([N:6]2[C:2]([NH:1][S:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:26])=[O:25])=[CH:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate (498 mg) synthesized according to the method described in WO2004/98589 and 4-dimethylaminopyridine (21 mg) were dissolved in pyridine (10 mL), and benzenesulfonyl chloride (461 mg) was added at room temperature. After stirring at 85° C. for 8 hr, 1 mol/L hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→ethyl acetate), and the obtained solid was washed with a mixed solvent of diisopropyl ether and ethyl acetate to give the title compound as a brown powder (yield 445 mg, yield 69%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with 1 mol/L hydrochloric acid, water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→ethyl acetate)
washthe obtained solid was washed with a mixed solvent of diisopropyl ether and ethyl acetate

Sources & evidence

ORD record: ord-f0bae3ff05e64d3c88d8eb78ee7db8cf
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334301B2

Reaction notes

Loading…