Methanol → N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]methanesulfonamide

HRID 915958Notes

Reaction equation

HRID 915958 reaction equation
CO.[CH:3]1([C:9]2[C:17]3[C:16](=[O:18])[NH:15][C:14]([C:19]4[CH:24]=[CH:23][C:22]([N:25](S(C)(=O)=O)[S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][C:20]=4[O:34][CH3:35])=[N:13][C:12]=3[N:11]([CH3:36])[N:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[OH-].[Na+]>O>[CH:3]1([C:9]2[C:17]3[C:16](=[O:18])[NH:15][C:14]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:21][C:20]=4[O:34][CH3:35])=[N:13][C:12]=3[N:11]([CH3:36])[N:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 136005960N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 136005815N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]methanesulfonamideYield 22.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2 ml methanol solution of 100 mg (0.20 mg) of the compound obtained in Example 141, 1 ml of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was diluted with water, and the dilution was washed with dichloromethane. The aqueous layer was acidified with a 2M aqueous solution of hydrochloric acid, and precipitated solids were collected by filtration, followed by drying and recrystallization to obtain 19 mg (22%) of the captioned compound.

Workup

  1. washthe dilution was washed with dichloromethane
  2. customprecipitated solids
  3. filtrationwere collected by filtration
  4. customby drying
  5. customrecrystallization

Sources & evidence

ORD record
ord-ee14cbf754f84fd9bd9e19ea23140b26
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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