Hydrochloric Acid → HCID 178429089, compound

HRID 254831Notes

Reaction equation

[NH2-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:20]=[C:19]([C:30](OCC)=[O:31])[C:18]=2[CH3:35])=[CH:13][CH:12]=1.Cl>C1COCC1>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:20]=[C:19]([C:30](=[O:31])/[CH:3]=[C:4](\[OH:9])/[C:5]([CH3:8])([CH3:7])[CH3:6])[C:18]=2[CH3:35])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of sodium amide (215 mg, 5.5 mmol) in THF (5 mL) was added pinacolone (1.0 M THF solution, 5 mL, 5.0 mmol). The reaction mixture was refluxed at 80° C. for 30 min and then ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate (4) (2.05 g, 5.0 mmol) in THF (15 mL) was added. The resulting solution was stirred and refluxed at 80° C. overnight. HCl aquous solution (11.0M, 50 mL) was added and extracted organic layer with ethyl acetate (50 mL twice). The combined organic phase was evaporated under vacuum. The crude residue was further purified by prep HPLC to provide 0.862 g (1.86 mmol, 37%) of the title compound.

Workup

temperaturerefluxed at 80° C. overnight
extractionextracted organic layer with ethyl acetate (50 mL twice)
customThe combined organic phase was evaporated under vacuum
customThe crude residue was further purified by prep HPLC

Sources & evidence

ORD record: ord-8ca88733c03b4795805f39eaa4d215a6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875647B2

Reaction notes

Loading…