1,4-Dioxane hydrochloride → HCID 68412145, compound

HRID 2359516Notes

Reaction equation

HRID 2359516 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].[ClH:29].O1CCOCC1>CO>[ClH:29].[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 204431481,4-Dioxane hydrochlorideHCID 250990892-(5-amino-4,6-dimethylpyrimidine-2-yloxy)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

Product 1

HCID 68412145HCID 68412145, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 65 (200 mg) was suspended in methanol (1 mL) and 4N HCl/1,4-dioxane solution (130 μL) 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 (2.0 mL) was added to the resulting residue and the mixture was stirred under reflux. Water (0.2 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 162 mg (74% yield) of the desired product as pale yellow crystals.

Workup

  1. dissolutionAfter the compound was dissolved
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThen, isopropanol (2.0 mL) was added to the resulting residue
  4. temperatureunder reflux
  5. additionWater (0.2 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-f1da26d40ead4136b7c81699d3c1e045
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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