Methanesulfonic Acid → HCID 178505344, compound

HRID 497929Notes

Reaction equation

HRID 497929 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]#[N:19])=[CH:17][C:12]=3[CH2:11][N:10]([S:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)(=[O:22])=[O:21])[C@H:9]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:8]2)[N:3]=[CH:2]1.[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>C(O)C>[S:36]([OH:39])(=[O:38])(=[O:37])[CH3:35].[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]#[N:19])=[CH:17][C:12]=3[CH2:11][N:10]([S:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)(=[O:21])=[O:22])[C@H:9]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:8]2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178509455HCID 178509455, compound

Product 1

HCID 178505344HCID 178505344, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example I was dissolved in anhydrous ethanol. The solution was heated to 60° C. Methanesulfonic acid was added at this temperature and a white slurry formed. The slurry was cooled to 0 to 5° C. over 1 hour and stirred for an additional 1 hour. The resulting white crystalline solid was filtered and washed with cold anhydrous ethanol. The wet cake was dried in a vacuum oven at 70° C. until the loss on drying (LOD) was <0.5% to afford the title product as a white, crystalline substance (13.2 g, 92.3% yield, HPLC AP >99). Typical yield is between about 92% to about 97%.

Workup

  1. customa white slurry formed
  2. temperatureThe slurry was cooled to 0 to 5° C. over 1 hour
  3. filtrationThe resulting white crystalline solid was filtered
  4. washwashed with cold anhydrous ethanol
  5. customThe wet cake was dried in a vacuum oven at 70° C. until the loss
  6. customon drying (LOD)

Sources & evidence

ORD record
ord-e4877bb1c29545d19fa98c97e298ef82
Source dataset
uspto-grants-2005_09
Patent number
US06949642B2

Reaction notes

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