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Dimethylformamide → 8-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

HRID 850180
Notes
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Reaction equation

HRID 850180 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[Cl:28][C:29]1[C:36]([N:37]([C:39](=[O:56])[CH2:40][NH:41][C:42](=[O:55])[CH:43]=[CH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51](=[O:54])[NH:52][CH3:53])=[CH:47][CH:46]=2)[CH3:38])=[CH:35][CH:34]=[C:33]([Cl:57])[C:30]=1[CH2:31]Br>O>[Cl:28][C:29]1[C:36]([N:37]([C:39](=[O:56])[CH2:40][NH:41][C:42](=[O:55])[CH:43]=[CH:44][C:45]2[CH:46]=[CH:47][C:48]([C:51](=[O:54])[NH:52][CH3:53])=[CH:49][CH:50]=2)[CH3:38])=[CH:35][CH:34]=[C:33]([Cl:57])[C:30]=1[CH2:31][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 110867028-Hydroxy-2-methyl-4-(2-pyridylmethoxy)quinolineHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

Product 1

HCID 545056398-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline
Yield 55.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cooled mixture of sodium hydride (40% in oil, 9 mg) and anhydrous N,N-dimethylformamide (1 ml) was added 8-hydroxy-2-methyl-4-(2-pyridylmethoxy)quinoline (53 mg), and the mixture was stirred at the same temperature for 30 minutes. To this mixture was added 2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide (103 mg), and the mixture was stirred at ambient temperature for 2.5 hours. Water (2 ml) was slowly added to the reaction mixture under ice-water cooling and the precipitates were collected by vacuum filtration and washed with water and diethyl ether. The crude product was purified by a preparative thin layer chromatography (chloroform-methanol-ammonium hydroxide) followed by trituration with ethyl acetate to give 8-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (77 mg) as a pinkish powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2.5 hours
  2. filtrationthe precipitates were collected by vacuum filtration
  3. washwashed with water and diethyl ether
  4. customThe crude product was purified by a preparative thin layer chromatography (chloroform-methanol-ammonium hydroxide)

Sources & evidence

ORD record
ord-60f80bf24d2740bbb1607c62447a3a50
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06015818

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes