Hydrochloric Acid → HCID 118023085, compound

HRID 2171827Notes

Reaction equation

HRID 2171827 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][NH:17][C:18]4([CH3:24])[CH2:23][CH2:22]S[CH2:20][CH2:19]4)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[ClH:28].OO.[O-:31][S:32]([O-:35])(=S)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CO.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[ClH:28].[CH3:27][C:2]1([CH3:1])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][NH:17][C:18]4([CH3:24])[CH2:23][CH2:22][S:32](=[O:35])(=[O:31])[CH2:20][CH2:19]4)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 118024107HCID 118024107, compound

Product 1

HCID 118023085HCID 118023085, compound

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 887MethanolSolvent

Procedure

To a suspension of N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-4-methyltetrahydro-2H-thiopyran-4-amine (55 mg) and sodium tungstate (IV) dihydrate (9.0 mg) in MeOH (1.1 mL) were sequentially added dropwise 1 M hydrochloric acid (313 μL) and a 35% hydrogen peroxide solution (56 μL) under ice-cooling, followed by stirring at the same temperature for 10 minutes, and further stirring at room temperature for 6 hours. To the reaction mixture that had been ice-cooled was added an aqueous Na2S2O3 solution, followed by stirring at room temperature for 30 minutes. Then, saturated aqueous sodium bicarbonate was added thereto, followed by extraction with chloroform. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column. The obtained purified product was dissolved in EtOAc, and 4 M HCl/dioxane was added dropwise thereto. The precipitate was collected by filtration and then dried under reduced pressure to obtain N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-4-methyltetrahydro-2H-thiopyran-4-amine-1,1-dioxidehydrochloride (22 mg).

Workup

  1. stirringfurther stirring at room temperature for 6 hours
  2. temperaturecooled
  3. stirringby stirring at room temperature for 30 minutes
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column
  9. customThe obtained purified product
  10. dissolutionwas dissolved in EtOAc
  11. addition4 M HCl/dioxane was added dropwise
  12. filtrationThe precipitate was collected by filtration
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-e36f76ae3c3f43a3b91604f39dc912ed
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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