Acetic Anhydride → HCID 24771267, compound

HRID 1670700Notes

Reaction equation

HRID 1670700 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:32]([CH:33]=1)[C:15]1[N:16]([C:25]3[CH:26]=[N:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[C:17](=[O:24])[C:18]3[C:23]([C:14]=1[N:13]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3.C(N(CC)CC)C>ClCCl>[Cl:31][C:28]1[N:27]=[CH:26][C:25]([N:16]2[C:15]3[N:32]4[CH:33]=[C:9]([NH:8][C:5](=[O:7])[CH3:6])[CH:10]=[CH:11][C:12]4=[N:13][C:14]=3[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:24])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24771431HCID 24771431, compound

Product 1

HCID 24771267HCID 24771267, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1.5 equiv., 0.829 mmol, 0.084 g) was added to a cooled (0° C.) solution of compound 53 (1.0 equiv., 0.553 mmol, 0.200 g) and triethylamine (1.5 equiv., 0.829 mmol, 0.085 g) in dichloromethane (6 ml). The reaction mixture was stirred at room temperature for 20 h. The solvent was evaporated under reduced pressure, and the resulting residue purified by column chromatography (dichloromethane/methanol 9:1; Rf=0.3) affording N-[6-(6-chloro-pyridin-3-yl)-5,6-dihydro-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl]-acetamide (56) (0.105 g, yield=47%, purity (LC)=90%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue purified by column chromatography (dichloromethane/methanol 9:1; Rf=0.3)

Sources & evidence

ORD record
ord-1a169e8318f143fc90a56dfc3d3b81f6
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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