Acetic Anhydride → HCID 18378615, compound

HRID 2298810Notes

Reaction equation

HRID 2298810 reaction equation
[NH2:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][C:12](=[O:34])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:20])=[CH:15][C:14]=3[O:32][CH3:33])[C:4]=2[N:3]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>>[C:35]([NH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][C:12](=[O:34])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:20])=[CH:15][C:14]=3[O:32][CH3:33])[C:4]=2[N:3]=1)(=[O:37])[CH3:36]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18378584HCID 18378584, compound

Product 1

HCID 18378615HCID 18378615, compound

Procedure

A mixture of N-(2-amino-1H-benzimidazol-4-yl)-2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (90 mg) and acetic anhydride (1.0 ml) was stirred for 1 hour at room temperature and allowed to stand overnight at the same temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The resulting solution was washed with saturated aqueous sodium hydrogencarbonate solution, water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-ethyl acetate=10-1) to give N-(2-acetamido-1H-benzimidazol-4-yl)-2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (42 mg).

Workup

  1. waitto stand overnight at the same temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe resulting solution was washed with saturated aqueous sodium hydrogencarbonate solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (chloroform-ethyl acetate=10-1)

Sources & evidence

ORD record
ord-dc2f84525310407ead32e0a1a71e314e
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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