Potassium hydroxy sulfite → (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-((R)-methylsulfinyl)-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one

HRID 41873Notes

Reaction equation

HRID 41873 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:26][CH3:27])[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]2[C@H:28]3[CH2:33][CH2:32][CH2:31][C@H:29]3[N:30]=[C:3]12.[OH:34]OS([O-])=O.[K+]>CC#N.CO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S@@:26]([CH3:27])=[O:34])[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=4)=[CH:17][CH:18]=3)[N:11]=[C:5]2[N:4]2[C@H:28]3[CH2:33][CH2:32][CH2:31][C@H:29]3[N:30]=[C:3]12

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 58456641HCID 58456641, compound

Product 1

HCID 58456653(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-((R)-methylsulfinyl)-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(methylthio)-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (35.2 mg, 0.076 mmol) is dissolved in CH3CN (0.5 mL) and CH3OH (2 mL), and then an aqueous solution of oxone (93.7 mg, 0.152 mmol) is added. The reaction mixture is stirred at room temperature for 20 h, and then purified by a semi-preparative HPLC to give pure product as white solids. MS (ESI) m/z 479.2 [M+H]+.

Workup

  1. custompurified by a semi-preparative HPLC
  2. customto give pure product as white solids

Sources & evidence

ORD record
ord-a87f7e5c6d0442dcafb89d1b64884809
Source dataset
uspto-grants-2013_09
Patent number
US08536159B2

Reaction notes

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