Acetic Anhydride → HCID 178474373, compound

HRID 1624933Notes

Reaction equation

HRID 1624933 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([NH2:16])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:15]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178508056HCID 178508056, compound

Product 1

HCID 178474373HCID 178474373, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Amino-1H-pyrazole-3-carboxylic acid (4-fluorophenyl)-amide (500 mg; 2.27 mmol) was dissolved in 5 ml of pyridine, treated with acetic anhydride (240 μl, 2.5 mmol) then stirred at room temperature overnight. The solvent was removed by evaporation then dichloromethane (20 ml) and 2M hydrochloric acid (20 ml) were added. The undissolved solid was collected by filtration, washed with more dichloromethane and water then dried under vacuum. The product was isolated as an off white solid (275 mg). (LC/MS: Rt 2.96, [M+H]+ 262.91).

Workup

  1. customThe solvent was removed by evaporation
  2. additiondichloromethane (20 ml) and 2M hydrochloric acid (20 ml) were added
  3. filtrationThe undissolved solid was collected by filtration
  4. washwashed with more dichloromethane and water
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-fe6e4f5b84dd4a7ebc4792dd076df723
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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