Methanesulfonic Acid → N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carboxamide methanesulfonate

HRID 55365Notes

Reaction equation

HRID 55365 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1([NH:12][C:13]([C:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:17]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[N:16]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>CC(C)=O>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1([NH:12][C:13]([C:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[N:17]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[N:16]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 104850Rimonabant

Product 1

HCID 86750772N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carboxamide methanesulfonateYield 96.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.84 g of methanesulfonic acid are added at 20°±3° C. to a solution of 18.55 g of the compound obtained in example 195 in 185 ml of acetone and the mixture is stirred for 20 hours at the same temperature. The white crystals formed are filtered off, washed with acetone and dried under vacuum to give 21.65 g of the expected product. DSC: melting, recrystallisation at about 175° C. then melting at 191.5° C. Thermogravimetry: weight less:about 5.2 % starting at 90° C.

Workup

  1. customThe white crystals formed
  2. filtrationare filtered off
  3. washwashed with acetone
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7806f4eac78243939b0c1ede32b29092
Source dataset
uspto-grants-1997_04
Patent number
US05624941

Reaction notes

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