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

HRID 1715800Notes

Reaction equation

HRID 1715800 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][O:25][CH2:24][CH2:23]3)[CH:8]=2)[N:3]=1.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>N1C=CC=CC=1>[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:1]([C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([O:29][CH3:28])=[CH:31][CH:32]=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]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:8]=3)[N:3]=2)=[O:35])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 116748882-Amino-3-cyano-4-benzylamino-6-morpholino-quinoline

Product 1

HCID 116859674-Methoxy-N-(4-methoxybenzoyl)-N-(6-(morpholin-4-yl)-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-(morpholin-4-yl)quinoline 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, and 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.: 157° 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-32cb05aaa25d458b95165e788ecd1c36
Source dataset
uspto-grants-2010_09
Patent number
US07799922B2

Reaction notes

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