5-Amino-4-[3-(2-aminosulfonylethenyl)benzoyl]-1-(4-fluorophenyl)pyrazole → 5-Amino-4-[3-(2-aminosulfonylethyl)benzoyl]-1-(4-fluorophenyl)pyrazole
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:22][S:23]([NH2:26])(=[O:25])=[O:24])[CH:16]=1>CO.[OH-].[Pd+2].[OH-]>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][S:23]([NH2:26])(=[O:24])=[O:25])[CH:16]=1Participants
4
Procedure
A mixture of 5-amino-4-[3-(2-aminosulfonylethenyl)benzoyl]-1-(4-fluorophenyl)-pyrazole (2.1 g, 5.43 mmol) and palladium hydroxide (0.6 g) in methanol (150 ml) was shaken in a Parr apparatus under hydrogen atmosphere at 50 psi. After 4 days, the reaction mixture was filtered through CELITE® and the filtrate was concentrated. The residue was purified by flash chromatography (elution gradient: 40-100% ethyl acetate/hexane) to give a crude product which was recrystallized from methanol/ethyl acetate/hexane to give 5-amino-4-[3-(2-aminosulfonylethyl)benzoyl]-1-(4-fluorophenyl)pyrazole (0.95 g, mpt. 170-170.4° C.) as a solid.
Workup
- filtrationthe reaction mixture was filtered through CELITE®
- concentrationthe filtrate was concentrated
- customThe residue was purified by flash chromatography (elution gradient: 40-100% ethyl acetate/hexane)
- customto give a crude product which
- customwas recrystallized from methanol/ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-441d6cf5bc804347a1f36d839fd78c80
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316466B1
Reaction notes
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