Hydrochloric Acid → HCID 58443379, compound

HRID 2067966Notes

Reaction equation

C[O:2][C:3](=[O:30])[CH2:4][CH:5]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)[NH:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[C:13]=1[CH3:14])=[O:8].[OH-].[Na+].Cl>>[Br:29][C:25]1[CH:24]=[C:23]([CH:5]([NH:6][C:7]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[C:13]=2[CH3:14])=[O:8])[CH2:4][C:3]([OH:30])=[O:2])[CH:28]=[CH:27][CH:26]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 44479601HCID 44479601, compound

Product 1

HCID 58443379HCID 58443379, compoundYield 60.3%

Procedure

3-(3-Bromo-phenyl)-3-{[1-(3,4-dichloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-amino}-propionic acid methyl ester (1.5 g, 2.9 mmol) is treated with aqueous NaOH (1.0 N solution, 60 mL, 60 mmol) and stirred at reflux for 1 hour. After cooling to room temperature, the reaction mixture is acidified with aqueous 1N HCl. The resultant precipitate is collected by filtration and dried in vacuo to afford 3-(3-bromo-phenyl)-3-{[1-(3,4-dichloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-amino}-propionic acid as a off-white solid (870 mg, 60%).

Workup

temperatureat reflux for 1 hour
filtrationThe resultant precipitate is collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-e9c059c357e8477b912973a97c385bba
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293917B2

Reaction notes

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