Maleic Acid → HCID 68413808, compound

HRID 1749314Notes

Reaction equation

HRID 1749314 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[N:4][C:5]([O:9][CH2:10][C:11]([N:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH3:14])=[O:12])=[N:6][C:7]=1[CH3:8].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>CO>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[NH2:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH2:10][C:11]([N:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:17][CH2:16]2)[CH3:14])=[O:12])=[N:4][C:3]=1[CH3:28]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 250990892-(5-amino-4,6-dimethylpyrimidine-2-yloxy)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

Product 1

HCID 68413808HCID 68413808, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 65 (1.0 g) was suspended in methanol (5.0 mL) and maleic acid (307 mg) was added to the suspension at room temperature (20 to 30° C.). After the compound was dissolved, the mixture was concentrated under reduced pressure. Then, isopropanol (5.0 mL) was added to the resulting residue and the mixture was stirred under reflux. Water (0.4 mL) was then added portionwise. Once the residue was dissolved, the mixture was stirred overnight as it was allowed to cool. Subsequently, the mixture was stirred and cooled with ice for 1 hour and was suction-filtered. The resulting solid was washed with isopropanol and dried to give 1.1 g (86% yield) of the desired product as white crystals.

Workup

  1. dissolutionAfter the compound was dissolved
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThen, isopropanol (5.0 mL) was added to the resulting residue
  4. temperatureunder reflux
  5. additionWater (0.4 mL) was then added portionwise
  6. dissolutionOnce the residue was dissolved
  7. stirringthe mixture was stirred overnight as it
  8. temperatureto cool
  9. stirringSubsequently, the mixture was stirred
  10. temperaturecooled with ice for 1 hour
  11. filtrationwas suction-filtered
  12. washThe resulting solid was washed with isopropanol
  13. customdried

Sources & evidence

ORD record
ord-f755f6c0e729430e9eaceb66573e1956
Source dataset
uspto-grants-2015_10
Patent number
US09156817B2

Reaction notes

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