HCID 9893845, compound → HCID 9937926, compound

HRID 352324Notes

Reaction equation

HRID 352324 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][S:25][CH2:24][CH2:23]2)=[N:11][CH:10]=1.[OH:39]OS([O-])=O.[K+]>CO>[F:38][C:2]([F:37])([F:1])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][S:25](=[O:39])[CH2:24][CH2:23]2)=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 9893845HCID 9893845, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 9937926HCID 9937926, compoundYield 159.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.24 g (2.24 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-thiomorpholin-4-yl-4-o-tolyl-nicotinamide (step a)) in 25 ml methanol were added 689 mg (1.12 mmol) Oxone® at 0° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. Quenching with 5 ml 40% aqueous sodium hydrogen sulfite solution was followed by addition of 6 ml 1N sodium hydroxide solution to adjust the pH to 7-8. The mixture was diluted with 50 ml water and extracted with 3 150-ml portions of dichloromethane. The combined extracts were dried with sodium sulfate and concentrated to give 1.20 g of crude product. Flash chromatography afforded 1.02 g (79.9%) of the title compound as a white solid.

Workup

  1. additionaddition the reaction mixture
  2. customQuenching with 5 ml 40% aqueous sodium hydrogen sulfite solution
  3. additionwas followed by addition of 6 ml 1N sodium hydroxide solution
  4. additionThe mixture was diluted with 50 ml water
  5. extractionextracted with 3 150-ml portions of dichloromethane
  6. dry with materialThe combined extracts were dried with sodium sulfate
  7. concentrationconcentrated
  8. customto give 1.20 g of crude product

Sources & evidence

ORD record
ord-1238e77d85264993ad48519fd4afbfde
Source dataset
uspto-grants-2004_06
Patent number
US06747026B2

Reaction notes

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