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

HRID 870452Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[C:11]([Cl:33])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[C:41](OC(=O)C)(=[O:43])[CH3:42]>>[C:41]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[C:11]([Cl:33])[CH:10]=2)[CH:5]=[CH:4][N:3]=1)(=[O:43])[CH3:42]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 8471Triethylamine

HCID 73053629N-(4-((2-aminopyridin-4-yl)oxy)-2-chloro-5-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 73053670N-(4-((2-acetamidopyridin-4-yl)oxy)-2-chloro-5-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 50.5%

Conditions

Temperature: 30 °C

Procedure

To a solution of N-(4-((2-aminopyridin-4-yl)oxy)-2-chloro-5-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (200 mg, 0.43 mmol) in acetic anhydride (4 mL) was added Et3N (400 mg, 2.6 mmol). The mixture was stirred at 30° C. for 12 hours and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1) to give the title compound as a light yellow solid (110 mg, 50.5%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1)

Sources & evidence

ORD record: ord-b5f5106e79e64fd6849c0530664bbc5a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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