p-Anisoyl chloride → 4-methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide

HRID 655698Notes

Reaction equation

HRID 655698 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]([CH3:24])[CH3:23])[CH:8]=2)[N:3]=1.[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:1]([C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[C:2]2[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([N:22]([CH3:24])[CH3:23])[CH:8]=3)[N:3]=2)=[O:32])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 668510232-Amino-3-cyano-4-benzylamino-6-dimethylaminoquinoline

Product 1

HCID 668507214-methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 0.4 g of 2-amino-3-cyano-4-benzylamino-6-dimethylaminoquinoline in 2 mL of pyridine, 0.4 mL of 4-methoxybenzoyl chloride is added under stirring and cooling. The reaction mixture is stirred at 80° C. for 8 hours, then poured onto 5 mL of ice-water. The precipitated material is filtered off, washed twice with 3 mL of water. After drying 0.53 g of the title compound is obtained, m.p.: 156° C.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred at 80° C. for 8 hours
  3. filtrationThe precipitated material is filtered off
  4. washwashed twice with 3 mL of water
  5. dry with materialAfter drying 0.53 g of the title compound
  6. customis obtained

Sources & evidence

ORD record
ord-20a824f2bc2843a1b2455063de4e1dc9
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

Loading…