Water → 8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline

HRID 2287466Notes

Reaction equation

HRID 2287466 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[Cl:18][C:19]1[C:26]([N:27]([CH3:46])[C:28](=[O:45])[CH2:29][NH:30][C:31](=[O:44])[CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40](=[O:43])[NH:41][CH3:42])=[CH:36][CH:35]=2)=[CH:25][CH:24]=[C:23]([Cl:47])[C:20]=1[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:18][C:19]1[C:26]([N:27]([CH3:46])[C:28](=[O:45])[CH2:29][NH:30][C:31](=[O:44])[CH:32]=[CH:33][C:34]2[CH:35]=[CH:36][C:37]([C:40](=[O:43])[NH:41][CH3:42])=[CH:38][CH:39]=2)=[CH:25][CH:24]=[C:23]([Cl:47])[C:20]=1[CH2:21][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 184042364-(1H-Imidazol-1-yl)-2-methylquinolin-8-olHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

Product 1

HCID 544674588-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinolineYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 8-hydroxy-4-(imidazol-1-yl)-2-methylquinoline (23 mg), 2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyl bromide (52.4 mg) and potassium carbonate (42.3 mg) in N,N-dimethylformamide (0.5 ml) was stirred for 3 hours at ambient temperature. Water was added thereto, and the resulting precipitate was collected by filtration. The residue was purified by preparative thin layer chromatography (chloroform:methanol, 10:1, v/v) to give 8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (60 mg) as colorless amorphous.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-4e035ca40b5f40799a4d61e73fb64767
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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