Methanesulfonic Acid → HCID 178446129, compound

HRID 730005Notes

Reaction equation

HRID 730005 reaction equation
[CH3:1][C:2]([CH3:38])([CH3:37])[CH2:3][N:4]1[C:8]2=[N:9][C:10]([C:13]3[N:14]=[C:15]([C:25]4[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][C:26]=4[F:35])[NH:16][C:17]=3[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH2:36].[CH3:39][S:40]([OH:43])(=[O:42])=[O:41]>CO>[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].[CH3:1][C:2]([CH3:38])([CH3:37])[CH2:3][N:4]1[C:8]2=[N:9][C:10]([C:13]3[N:14]=[C:15]([C:25]4[C:30]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:28]=[CH:27][C:26]=4[F:35])[NH:16][C:17]=3[C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH2:36]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178446128HCID 178446128, compound

Product 1

HCID 178446129HCID 178446129, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Mix 3-(2,2-dimethyl-propyl)-5-[5-(4-fluoro-phenyl)-2-(2-fluoro-6-trifluoromethyl-phenyl) -1H-imidazol-4-yl]-3H-imidazo[4,5-b]pyridin-2-ylamine (11.56 g, 21.95 mmol) in methanol (150 mL), and then add a solution of methanesulfonic acid (2.11 g, 21.96 mmol) in MeOH (10 mL) dropwise. Allow the resulting reaction mixture to stir at room temperature for 20 minutes, then concentrate under reduced pressure. Slurry the residue in diethyl ether, filter, and wash with fresh diethyl ether. Dry the resulting solid in a drying oven at room temperature under house vacuum for 48 h to give 12.015 g (87.9% yield) of the title compound as a light-purple solid.

Workup

  1. customthe resulting reaction mixture
  2. concentrationconcentrate under reduced pressure
  3. filtrationfilter
  4. washwash with fresh diethyl ether
  5. customDry the resulting solid in a drying oven at room temperature under house vacuum for 48 h

Sources & evidence

ORD record
ord-0883e78012ab4577be485734a972f958
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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