Maleic Acid → HCID 131730218, compound

HRID 388511Notes

Reaction equation

HRID 388511 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:31][C:32]([CH2:34][C:35]1([CH2:38][C:39]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)=[O:40])[CH2:37][CH2:36]1)=[O:33].[C:49]([OH:56])(=[O:55])/[CH:50]=[CH:51]\[C:52]([OH:54])=[O:53]>CC(C)=O>[C:49]([OH:56])(=[O:55])/[CH:50]=[CH:51]\[C:52]([OH:54])=[O:53].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:31][C:32]([CH2:34][C:35]1([CH2:38][C:39]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)=[O:40])[CH2:37][CH2:36]1)=[O:33]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 131730213HCID 131730213, compound

Product 1

HCID 131730218HCID 131730218, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

After suspending N-(2-fluoro-4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxyamide (65.3 mg) in acetone (1.306 ml), maleic acid (12.0 mg) was added. The suspension was sonicated and then stirred at 50° C. for 5 minutes to form a solution. The solution was stirred at room temperature for 16 hours and stirred at 4° C. for 4 days. The precipitate was collected by filtration under a nitrogen stream. After washing with acetone (0.020 ml), it was dried under aeration at room temperature for 2 hours to give the title compound (15.1 mg, 20%) as white powder.

Workup

  1. additionwas added
  2. customThe suspension was sonicated
  3. customto form a solution
  4. stirringThe solution was stirred at room temperature for 16 hours
  5. stirringstirred at 4° C. for 4 days
  6. filtrationThe precipitate was collected by filtration under a nitrogen stream
  7. washAfter washing with acetone (0.020 ml), it
  8. customwas dried under aeration at room temperature for 2 hours

Sources & evidence

ORD record
ord-89b6f4b8fdc64db9a6d2a5980ee2f22f
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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