Water → HCID 73426361, compound

HRID 1507597Notes

Reaction equation

HRID 1507597 reaction equation
[CH:1]1([S:4][CH2:5][CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:15]=3)[C:10]([CH3:27])([CH3:26])[C:9]2=[O:28])[CH2:3][CH2:2]1.[OH:29]OS([O-])=O.[K+].[OH2:35]>CO>[CH:1]1([S:4]([CH2:5][CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:15]=3)[C:10]([CH3:26])([CH3:27])[C:9]2=[O:28])(=[O:29])=[O:35])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 90046331HCID 90046331, compound

Product 1

HCID 73426361HCID 73426361, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(1-(3-(cyclopropylthio)propyl)-3,3-dimethyl-2-oxoindolin-6-yl)isonicotinamide (130 mg, 329 μmol) in methanol (1 ml) was added dropwise a solution of oxone (303 mg, 493 μmol) in water (1.00 ml). After 2 hours at room temperature the reaction mixture was poured into water and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel using dichloromethane/methanol as eluent. The title compound was obtained as white foam (91 mg).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washThe combined organic layers were washed with saturated NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-678857abea0e423e8a70a9fdcf9d0eb8
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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