Methanesulfonic Acid → HCID 178446135, compound

HRID 730024Notes

Reaction equation

HRID 730024 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH2:19])=[N:18][C:13]3=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>CO.CCOC(C)=O>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[C:1]([C:5]1[NH:6][C:7]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH2:19])=[N:18][C:13]3=[CH:12][CH:11]=2)[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178446132HCID 178446132, compound

Product 1

HCID 178446135HCID 178446135, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Heat a solution of 5-[2-tert-Butyl-5-(4-fluoro-phenyl)-1H-imidazol-4-yl]-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine (10.0853 g, 23.98 mmol) in MeOH (24 mL) to 40° C. Remove heat source and add methanesulfonic acid (3.14 mL, 47.91 mmol) in EtOAc (10 mL) dropwise over 3.5 minutes. Stir for 1 h while cooling to room temperature. Add EtOAc (20 mL) and stir 5 minutes. Filter, wash solid with 2×50 mL EtOAc, and dry under reduced pressure at 45-50° C. for 2.5 h to provide 12.62 g (86%) of the title compound as a white powder solid.

Workup

  1. customRemove
  2. temperatureheat source
  3. filtrationFilter
  4. washwash solid with 2×50 mL EtOAc
  5. customdry under reduced pressure at 45-50° C. for 2.5 h

Sources & evidence

ORD record
ord-592f1891df96476bb6fe1ae648c7ea06
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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