Acetic Acid → HCID 66850392, compound

HRID 655691Notes

Reaction equation

HRID 655691 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-68aceb5b0de24e52943aba9d94c9d355
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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