m-Anisoyl chloride → 3-Methoxy-N-[6-(4-acetylpiperazin-1-yl)-4-benzylamino-3-cyanoquinolin-2-yl]benzamide

HRID 2195697Notes

Reaction equation

HRID 2195697 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]3)[CH:8]=2)[N:3]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](Cl)=[O:37]>N1C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36]([NH:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH2:27]3)[CH:8]=2)[N:3]=1)=[O:37]

Participants

4

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 670236072-Amino-3-cyano-4-benzylamino-6-(4-acetylpiperazin-1-yl)quinoline

Product 1

HCID 670236583-Methoxy-N-[6-(4-acetylpiperazin-1-yl)-4-benzylamino-3-cyanoquinolin-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 1.2 g 2-amino-3-cyano-4-benzylamino-6-(4-acetylpiperazin-1-yl)quinoline in 20 ml pyridine, 1.5 g 3-methoxybenzoyl chloride is added and the mixture is heated at reflux temperature for 5 hours. The reaction mixture is poured onto 30 g ice-water and the precipitated solid material is filtered off. After drying 0.45 g of the title compound is obtained (MH+: 535).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature for 5 hours
  3. filtrationthe precipitated solid material is filtered off
  4. dry with materialAfter drying 0.45 g of the title compound
  5. customis obtained (MH+: 535)

Sources & evidence

ORD record
ord-c37d07c2effe49d1b8da2826319c5ec0
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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