Hydrogen Bromide → HCID 68411662, compound

HRID 1749312Notes

Reaction equation

HRID 1749312 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].[BrH:29]>CO>[BrH: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 260Hydrogen BromideHCID 250990892-(5-amino-4,6-dimethylpyrimidine-2-yloxy)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

Product 1

HCID 68411662HCID 68411662, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 65 (198 mg) was suspended in methanol (1 mL) and hydrobromic acid (89 mg: 47% aqueous solution) was added to the suspension at room temperature (20 to 30° C.). After the compound was dissolved, the mixture was concentrated under reduced pressure. Ethanol (3 mL) was added to the resulting residue and the mixture was stirred under reflux. Water (0.6 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 ethanol and dried to give 189 mg (78% yield) of the desired product as white crystals.

Workup

  1. dissolutionAfter the compound was dissolved
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionEthanol (3 mL) was added to the resulting residue
  4. temperatureunder reflux
  5. additionWater (0.6 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 ethanol
  13. customdried

Sources & evidence

ORD record
ord-244fe0079b2f48ada9af7a4d105e9ccc
Source dataset
uspto-grants-2015_10
Patent number
US09156817B2

Reaction notes

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