Nitric Acid → HCID 68416053, compound

HRID 2359519Notes

Reaction equation

HRID 2359519 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].[N+:29]([O-:32])([OH:31])=[O:30]>CO>[N+:29]([O-:32])([OH:31])=[O:30].[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 944Nitric AcidHCID 250990892-(5-amino-4,6-dimethylpyrimidine-2-yloxy)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

Product 1

HCID 68416053HCID 68416053, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 65 (186 mg) was suspended in methanol (1 mL) and nitric acid (44.3 mg: d=1.42) 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 (240 μL) 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 116 mg (54% 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 (2.0 mL) was added to the resulting residue
  4. temperatureunder reflux
  5. additionWater (240 μL) 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-c14307520aa84d489bac363a06f5c916
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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