Acetic Acid → HCID 66850392, compound

HRID 1985674Notes

Reaction equation

HRID 1985674 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([C:7]([N:9](C(=O)C2C=CC(OC)=CC=2)[C:10]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:16]=3)[N:11]=2)=[O:8])=[CH:5][CH:4]=1.C(O)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C.[OH-].[K+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:16]=3)[N:11]=2)=[O:8])=[CH:47][CH:48]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 66850723HCID 66850723, compound

Product 1

HCID 66850392HCID 66850392, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14797Potassium HydroxideSolvent

Procedure

To the solution of 2.3 g of 4-methoxy-N-(4-methoxybenzoyl)-N-(6-(4-methylpiperazino)-4-benzylamino-3-cyanoquinolin-2-yl)benzamide in 15 mL of acetonitrile, 4 mL of 1N methanolic potassium hydroxide solution is added. The reaction mixture is heated under reflux conditions for 10 minutes, 1 mL of glacial acetic acid is added to it, then it is neutralized with 12 mL of 1M sodium hydrogen carbonate solution. The precipitate is filtered off, the yellow crystalline material is recrystallized from the mixture of 15 mL of methanol and 35 mL of water. After drying 1.1 g of the title compound is obtained, m.p.: 173° C.

Workup

  1. temperatureThe reaction mixture is heated under reflux conditions for 10 minutes
  2. filtrationThe precipitate is filtered off
  3. customthe yellow crystalline material is recrystallized from the mixture of 15 mL of methanol and 35 mL of water
  4. dry with materialAfter drying 1.1 g of the title compound
  5. customis obtained

Sources & evidence

ORD record
ord-c10f781ecb4542aab4f7e8093142247f
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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