Water → HCID 66732814, compound

HRID 1966820Notes

Reaction equation

HRID 1966820 reaction equation
CS(O[CH2:6][C:7]1([CH2:30][CH2:31]OS(C)(=O)=O)O[N:10]=[C:9]([C:12]2[C:13]([NH:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:14]3[CH:20]=[N:19][N:18]([CH2:21][CH3:22])[C:15]3=[N:16][CH:17]=2)[CH2:8]1)(=O)=O.[S-2:37].[Na+].[Na+].[OH2:40]>CN(C)C=O>[CH:24]1([NH:23][C:13]2[C:14]3[CH:20]=[N:19][N:18]([CH2:21][CH3:22])[C:15]=3[N:16]=[CH:17][C:12]=2[C:9]2[CH2:8][C:7]3([CH2:30][CH2:31][S:37][CH2:6]3)[O:40][N:10]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 14804Sodium SulfideHCID 86647600HCID 86647600, compound

Product 1

HCID 66732814HCID 66732814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

(3-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-5-{2-[(methylsulfonyl)oxy]ethyl}-4,5-dihydroisoxazol-5-yl)methyl methanesulfonate (280 mg, 0.00051 mole) (example 12) was taken in dimethylformamide (5 ml). Sodium sulphide nanohydrate (372 mg, 0.0015 mole) was added. The reaction mixture was refluxed at 90-100° C. overnight. Water was added, extraction was done with ethyl acetate, the organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuum. Purification was done by preparative thin layer chromatography by using ethyl acetate (40%) in hexane solvent.

Workup

  1. extractionextraction
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuum
  5. customPurification

Sources & evidence

ORD record
ord-630d1a6c98c5427a9d9d6bb1cd10cb9d
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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