Methanesulfonic Acid → Piperidine-4-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide methane sulfonate

HRID 1020051Notes

Reaction equation

HRID 1020051 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[CH:10]=1.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>CO.C(Cl)(Cl)Cl>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[CH:10]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59508946Piperidine-4-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide

Product 1

HCID 86645893Piperidine-4-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide methane sulfonateYield 89%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a clear solution of piperidine-4-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #6A) (2.5 g, 8 mmol) in methanol:chloroform (1:1, 75 ml) was added methane sulfonic acid (5 ml, 80 mmol) dropwise at 0° C. and the formed clear solution was stirred at room temperature for half an hour. A white solid precipitated out and diethyl ether (150 ml) was added to precipitate more of the solid which was then filtered off and washed with diethyl ether (50 ml). This crude solid was dissolved in 90 ml of chloroform: methanol (2:1) and the mixture heated at 60° C. to become a clear solution. Then diethyl ether (90 ml) was added and the turbid solution was kept at room temperature for one hour. The formed crystalline solid was filtered off, washed with diethyl ether (50 ml) and dried under high vacuum to give piperidine-4-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide methane sulfonate (compound #15A, methane sulfonic acid salt of compound #6A) (2.9 g, 89%) as a white solid.

Workup

  1. customA white solid precipitated out and diethyl ether (150 ml)
  2. additionwas added
  3. customto precipitate more of the solid which
  4. filtrationwas then filtered off
  5. washwashed with diethyl ether (50 ml)
  6. dissolutionThis crude solid was dissolved in 90 ml of chloroform: methanol (2:1)
  7. temperaturethe mixture heated at 60° C.
  8. additionThen diethyl ether (90 ml) was added
  9. filtrationThe formed crystalline solid was filtered off
  10. washwashed with diethyl ether (50 ml)
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-a7198252f425479db571932d8f2e6a85
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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