Potassium Carbonate → 2-[3-(acetylamino)-4-nitro-1H-pyrazol-1-yl]-N-(3-fluorophenyl)acetamide

HRID 639977Notes

Reaction equation

[N+:1]([C:4]1[C:5]([NH:9][C:10](=[O:12])[CH3:11])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:10]([NH:9][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][N:7]([CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[O:16])[N:6]=1)(=[O:12])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(4-nitro-1H-pyrazol-3-yl)acetamide (0.380 g, 2.25 mmol), 2-chloro-N-(3-fluorophenyl)acetamide (0.420 g, 2.25 mmol) and potassium carbonate (00.370 g, 2.7 mmol) in dimethyl formamide (10 ml) was heated at 50° C. for 1 hour. The mixture was filtered and the filtrate was evaporated. The residue was triturated with a mixture of 2% methanol in dichloromethane and then with diethyl ether to give 2-[3-(acetylamino)-4-nitro-1H-pyrazol-1-yl]-N-(3-fluorophenyl)acetamide

Workup

filtrationThe mixture was filtered
customthe filtrate was evaporated
customThe residue was triturated with a mixture of 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-44c5b635ffc045d0b7dcd093a1747cde
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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