Methanesulfonic Acid → HCID 178505361, compound

HRID 1946291Notes

Reaction equation

HRID 1946291 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[C:9]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH2:22][N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[CH:21][C:15]=4[N:14]=3)=[N:10][NH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>CO.CCOC(C)=O>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH:1]1([NH:4][C:5]([NH:7][C:8]2[C:9]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH2:22][N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)=[CH:21][C:15]=4[N:14]=3)=[N:10][NH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178522431HCID 178522431, compound

Product 1

HCID 178505361HCID 178505361, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 1-cyclopropyl-3-[3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-urea free base (394 mg) in MeOH-EtOAc was added 1 equivalent of methanesulfonic acid (67 μl). A solid was formed which was collected by filtration, washing with EtOAc. The solid was dissolved in the minimum amount of hot MeOH, allowed to cool and then triturated with Et2O. The solid was left to stand for 72 h and then collected by filtration, washing with MeOH, to give 1-cyclopropyl-3-[3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-urea methanesulfonate salt.

Workup

  1. customA solid was formed which
  2. filtrationwas collected by filtration
  3. washwashing with EtOAc
  4. dissolutionThe solid was dissolved in the minimum amount of hot MeOH
  5. temperatureto cool
  6. customtriturated with Et2O
  7. waitThe solid was left
  8. filtrationcollected by filtration
  9. washwashing with MeOH

Sources & evidence

ORD record
ord-d7b5171402a44a80898514415e7cabc4
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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