Acetic Anhydride → N-[3-(1H-1,3-benzodiazol-2-yl)-1H-pyrazol-4-yl]acetamide

HRID 1012053Notes

Reaction equation

HRID 1012053 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[C:21]([NH2:22])=[CH:20][NH:19][N:18]=1>N1C=CC=CC=1>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[C:21]([NH:22][C:5](=[O:7])[CH3:6])=[CH:20][NH:19][N:18]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178508052HCID 178508052, compound

Product 1

HCID 178474371N-[3-(1H-1,3-benzodiazol-2-yl)-1H-pyrazol-4-yl]acetamideYield 48.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (27 μl, 0.28 mmol) was added to a solution of 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.25 mmol) in pyridine (5 ml) and the reaction mixture stirred at ambient temperature for 24 h. The mixture was reduced in vacuo and the residue purified by flash column chromatography [SiO2, EtOAc-petrol (1:2.5, 2:1)] to give N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-acetamide as a brown crystalline solid (29 mg, 48%). (LC/MS: Rt 1.70, [M+H]+ 241.64).

Workup

  1. customthe residue purified by flash column chromatography [SiO2, EtOAc-petrol (1:2.5, 2:1)]

Sources & evidence

ORD record
ord-2a36719c2c0c40d7b8ede54c1a5d11b5
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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