Methanol → HCID 70817269, compound

HRID 82110Notes

Reaction equation

HRID 82110 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[C:24]([C:26]([C:28]3[C:36]4[CH:35]=[N:34][CH:33]=[N:32][C:31]=4[N:30]([CH2:37]SC)[CH:29]=3)=[O:27])[CH:25]=2)=[O:18])=[CH:12][CH:11]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[CH3:49]O>O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[C:24]([C:26]([C:28]3[C:36]4[CH:35]=[N:34][CH:33]=[N:32][C:31]=4[N:30]([CH2:37][S:1]([CH3:49])(=[O:6])=[O:2])[CH:29]=3)=[O:27])[CH:25]=2)=[O:18])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 656671Sodium PyrosulfiteHCID 10313463Potassium peroxymonosulphateHCID 708177472-(4-chlorophenyl)-N-[5-({7-[(methylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]acetamide

Product 1

HCID 70817269HCID 70817269, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium peroxomonosulfate (Oxone, 67.2 mg, 0.110 mmol) was added to a stirring solution of 2-(4-chlorophenyl)-N-[5-({7-[(methylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]acetamide (Example 313, 25.0 mg, 0.055 mmol) in methanol (1.0 mL) and water (0.25 mL) at 0° C. After 1 hour, the reaction was allowed to warm to room temperature and stirred for 24 hours. The reaction mixture was cooled to 0° C. and sodium metabisulfite (0.5M, 1 ml) was added. The reaction mixture was evaporated under reduced pressure to remove the methanol. Water (3 mL) was added to the mixture and it was extracted with EtOAc (3×5 mL). The combined organic fractions were washed with water (5 mL), brine (5 mL), dried over magnesium sulfate the solvent was removed under reduced pressure to give the crude product as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto remove the methanol
  4. additionWater (3 mL) was added to the mixture and it
  5. extractionwas extracted with EtOAc (3×5 mL)
  6. washThe combined organic fractions were washed with water (5 mL), brine (5 mL)
  7. dry with materialdried over magnesium sulfate the solvent
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-dca3888232fc470baebefdccf15e9cb9
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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