Sodium Carbonate → HCID 10304406, compound

HRID 22648Notes

Reaction equation

HRID 22648 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C:13]([CH3:38])([CH3:37])[C:14]([N:16]([CH3:36])[C:17]2[CH:18]=[N:19][C:20]([N:30]3[CH2:35][CH2:34]S[CH2:32][CH2:31]3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O[O:42][S:43]([O-:45])=O.[K+].S([O-])(O)=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:38])([CH3:37])[C:14]([N:16]([C:17]2[CH:18]=[N:19][C:20]([N:30]3[CH2:31][CH2:32][S:43](=[O:45])(=[O:42])[CH2:34][CH2:35]3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH3:36])=[O:15])[CH:4]=[C:3]([C:2]([F:39])([F:40])[F:1])[CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 112501862-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramideHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10304406HCID 10304406, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.00 g (1.72 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide in 10 ml methanol were added 1.59 g (2.58 mmol) OXONE®. After stirring for 2 days at room temperature, 5 ml 38% sodium hydrogensulfite solution and 20 ml saturated sodium carbonate solution were added consecutively and methanol was removed in vacuo. The residue was diluted with 25 ml water and extracted with three 25-ml portions of dichloromethane. The combined organic layers were dried (sodium sulfate), purified by flash chromatography and crystallized from ethanol to give 980 mg (93%) of the title compound as white crystals. M.p. 200-201° C.

Workup

  1. custommethanol was removed in vacuo
  2. additionThe residue was diluted with 25 ml water
  3. extractionextracted with three 25-ml portions of dichloromethane
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. custompurified by flash chromatography
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-2318b35b29504f0ba66fc5ea24422cc2
Source dataset
uspto-grants-2005_02
Patent number
US06849624B2

Reaction notes

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