Acetic Anhydride → N-(4-((2-acetamidopyridin-4-yl)oxy)-2-chlorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 870435Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[C:11]([Cl:32])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>>[C:40]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[C:11]([Cl:32])[CH:10]=2)[CH:5]=[CH:4][N:3]=1)(=[O:42])[CH3:41]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 8471Triethylamine

HCID 73053612N-(4-((2-aminopyridin-4-yl)oxy)-2-chlorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 73053669N-(4-((2-acetamidopyridin-4-yl)oxy)-2-chlorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 63%

Conditions

Temperature: 35 °C

Procedure

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)-2-chlorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (125 mg, 0.28 mmol) in acetic anhydride (6.0 mL) was added triethylamine (0.4 mL). The reaction mixture was stirred at 35° C. for 13 hours, then filtered, and the filter cake was washed with petroleum ether (6 mL), MeOH (3 mL), and ethyl acetate (6 mL) respectively to give the title compound as a light blue solid (87 mg, 63%).

Workup

filtrationfiltered
washthe filter cake was washed with petroleum ether (6 mL), MeOH (3 mL), and ethyl acetate (6 mL) respectively

Sources & evidence

ORD record: ord-fe8ace577de1494f831d0be40fff3a14
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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