p-Anisoyl chloride → 4-Methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-[2-thienylmethylamino]-3-cyanoquinolin-2-yl)benzamide

HRID 1985687Notes

Reaction equation

HRID 1985687 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:21]([CH3:23])[CH3:22])[CH:8]=2)[N:3]=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:1]([C:30](=[O:31])[C:29]2[CH:33]=[CH:34][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[C:2]2[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([N:21]([CH3:23])[CH3:22])[CH:8]=3)[N:3]=2)=[O:31])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 668505672-Amino-3-cyano-4-[2-thienylmethylamino]-6-dimethylaminoquinoline

Product 1

HCID 668503774-Methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-[2-thienylmethylamino]-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-[2-thienylmethylamino]-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 0.43 g of the title compound is obtained, m.p.: 171° 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 0.43 g of the title compound
  6. customis obtained

Sources & evidence

ORD record
ord-d4ebe04b078146819df7f2651f219cc2
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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