Methanesulfonic Acid → HCID 11236900, compound

HRID 639492Notes

Reaction equation

HRID 639492 reaction equation
[CH3:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:9]=[C:10]([C:12]([NH:14][CH2:15][C@@H:16]([OH:18])[CH3:17])=[O:13])[CH:11]=1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>C(O)(C)C>[S:30]([OH:33])(=[O:32])(=[O:31])[CH3:29].[CH3:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([CH3:1])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:9]=[C:10]([C:12]([NH:14][CH2:15][C@@H:16]([OH:18])[CH3:17])=[O:13])[CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 11176458HCID 11176458, compound

Product 1

HCID 11236900HCID 11236900, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

8-[(2,6-dimethylbenzyl)amino]-N-[(2S)-2-hydroxypropyl]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide (29.0 g, 0.0762 mol) was dissolved in refluxing isopropanol (280 ml). Methanesulfonic acid (7.4 g, 0.0770 mol), dissolved in isopropanol (20 ml), was added to the solution. When cooled, a crystalline substance precipitated. The mixture was left over night at room temperature. The product was filtered off and washed with isopropanol. 29.9 g of the compound of the invention as mesylate salt was obtained.

Workup

  1. additionwas added to the solution
  2. temperatureWhen cooled
  3. customa crystalline substance precipitated
  4. waitThe mixture was left over night at room temperature
  5. filtrationThe product was filtered off
  6. washwashed with isopropanol

Sources & evidence

ORD record
ord-050bb7a8b5c64b3eb49c6c82aa7e97fd
Source dataset
uspto-grants-2010_04
Patent number
US07691875B2

Reaction notes

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