Methanesulfonic Acid → HCID 86641960, compound

HRID 2359518Notes

Reaction equation

HRID 2359518 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].[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>CO>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[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 6395Methanesulfonic AcidHCID 250990892-(5-amino-4,6-dimethylpyrimidine-2-yloxy)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

Product 1

HCID 86641960HCID 86641960, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 65 (202 mg) was suspended in methanol (1 mL) and methanesulfonic acid (50.6 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 (1.0 mL) was added to the resulting residue and the mixture was stirred under reflux. 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 232 mg (92% 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 (1.0 mL) was added to the resulting residue
  4. temperatureunder reflux
  5. dissolutionOnce the residue was dissolved
  6. stirringthe mixture was stirred overnight as it
  7. temperatureto cool
  8. stirringSubsequently, the mixture was stirred
  9. temperaturecooled with ice for 1 hour
  10. filtrationwas suction-filtered
  11. washThe resulting solid was washed with isopropanol
  12. customdried

Sources & evidence

ORD record
ord-126ba1ffe4b641cc95d20bffb641895c
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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