Acetic Anhydride → N-acetyl-1-benzyl-3-[(4{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxamide

HRID 2221724Notes

Reaction equation

HRID 2221724 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)[O:29][C:30]=3[CH3:31])=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>>[C:37]([NH:15][C:13]([C:11]1[C:10]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)[O:29][C:30]=3[CH3:31])=[CH:22][CH:23]=2)=[N:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=1)=[O:14])(=[O:39])[CH3:38]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 692176221-benzyl-3-[(4{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxamide

Product 1

HCID 69217650N-acetyl-1-benzyl-3-[(4{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxamideYield 48%

Procedure

A mixture of 1-benzyl-3-[(4{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxamide (0.50 g) and acetic anhydride (20 mL) was heated under reflux for 4 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine and concentrated to give N-acetyl-1-benzyl-3-[(4{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxamide as colorless crystals (0.25 g, yield 48%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 193-194° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9ee0e8db03b4ce8a5d5985a8b1760a3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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