Methanesulfonic Acid → HCID 178446127, compound

HRID 730004Notes

Reaction equation

HRID 730004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[C:12]([C:14]2[N:19]=[C:18]3[N:20]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]([NH2:23])=[N:22][C:17]3=[CH:16][CH:15]=2)[N:13]=1.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>CO>[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)=[C:12]([C:14]2[N:19]=[C:18]3[N:20]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]([NH2:23])=[N:22][C:17]3=[CH:16][CH:15]=2)[N:13]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178446126HCID 178446126, compound

Product 1

HCID 178446127HCID 178446127, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Mix 5-[2-(2,6-dichloro-phenyl)-5-(4-fluoro-phenyl)-1H-imidazol-4-yl]-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine (11.20 g, 21.99 mmol) in methanol (150 mL), and then add a solution of methanesulfonic acid (2.11 g, 21.96 mmol) in methanol (10 mL) dropwise. Stir at room temperature for 20 minutes and then concentrate under reduced pressure. Add ethyl acetate (150 mL), filter resulting slurry, and wash filter cake with diethyl ether (200 mL). Dry the resulting solid in a drying oven at 80° C. under house vacuum for 2 h to give 12.765 g (95% yield) of the title compound as a light-purple solid.

Workup

  1. concentrationconcentrate under reduced pressure
  2. filtrationAdd ethyl acetate (150 mL), filter
  3. customresulting slurry
  4. washwash
  5. filtrationfilter cake with diethyl ether (200 mL)
  6. customDry the resulting solid in a drying oven at 80° C. under house vacuum for 2 h

Sources & evidence

ORD record
ord-d1165cb42e4643c1804030bab9deb3e5
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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