Water → HCID 24771705, compound

HRID 1670703Notes

Reaction equation

HRID 1670703 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21]3[N:22]4[CH:28]=[C:27]([NH:29][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:26]=[CH:25][C:23]4=[N:24][C:20]=3[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:37])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:38]I.O>CN(C=O)C>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:21]3[N:22]4[CH:28]=[C:27]([N:29]([CH3:38])[C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:26]=[CH:25][C:23]4=[N:24][C:20]=3[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:37])=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24771704HCID 24771704, compound

Product 1

HCID 24771705HCID 24771705, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.6 equiv., 1.029 mmol, 0.041 g (60%)) was added to a solution of 86 (1.0 equiv., 0.643 mmol, 0.302 g) in DMF (15 ml), the reaction mixture was stirred for 1 h at room temperature. Methyl iodide (1.2 equiv., 0.772 mmol, 0.110 g) was added and the mixture was stirred at room temperature for 24 h. Water was added to the reaction mixture, and the formed precipitate was filtered off and washed with water and isopropyl ether to give N-[5,6-dihydro-6-(4-nitrophenyl)-5-oxo-pyrido[2′,1′:2,3]-imidazo[4,5-c]isoquinolin-9-yl]-N-methyl-hexanamide (87) (0.296 g, yield=95%, purity (LC)=93%).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. filtrationthe formed precipitate was filtered off
  3. washwashed with water and isopropyl ether

Sources & evidence

ORD record
ord-260f8cf4fe0a4977831bc263c51126c6
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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