Ethanol → 3-[5-Amino-4-(3-methoxybenzoyl)-pyrazol-1-yl]-4-methylbenzoic acid

Reaktionsgleichung

Cl[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([C:7](=[CH:10]NC1C=CC=CC=1)[C:8]#[N:9])=[O:6].Cl.[NH:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[CH3:33])[C:27]([OH:29])=[O:28])[NH2:23].C(N(CC)CC)C.[CH2:41]([OH:43])C>>[NH2:9][C:8]1[N:22]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=2[CH3:33])[C:27]([OH:29])=[O:28])[N:23]=[CH:10][C:7]=1[C:5](=[O:6])[C:4]1[CH:18]=[CH:19][CH:20]=[C:2]([O:43][CH3:41])[CH:3]=1

Komponenten

Edukt 4

HCID 702Ethanol

HCID 8471Triethylamine

HCID 567775083-Hydrazino-4-methylbenzoic acid hydrochloride

HCID 670242262-(3-Chlorobenzoyl)-3-phenylaminoacrylonitrile

Produkt 1

HCID 582007813-[5-Amino-4-(3-methoxybenzoyl)-pyrazol-1-yl]-4-methylbenzoic acid

Versuchsvorschrift

A solution of 2-(3-chlorobenzoyl)-3-phenylaminoacrylonitrile (63 mg, 0.22 mmol, 1.0 eq), 3-hydrazino-4-methylbenzoic acid hydrochloride (72 mg, 0.22 mmol, 1 eq), and triethylamine (31 μL, 0.22 mmol, 1.0 eq) in 10 mL of ethanol was heated to 65° C. for 20 h. After cooling, the mixture was concentrated and the residue purified by flash chromatography on silica gel packed and eluted with 7/3 hexanes/ethyl acetate to remove byproducts followed by 3/2 ethyl acetate/hexanes to elute the title compound (15 mg, 32%) as a brown solid. HPLC (4 minute 10-90 gradient) tR 2.13 min; MS m/z 352.2 [M+H]+.