Befetupitant → HCID 10144852, compound

HRID 1168331Notes

Reaction equation

HRID 1168331 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][C:8]([F:46])([F:45])[C:9]1[CH:10]=[C:11]([C:19]([CH3:44])([CH3:43])[C:20]([N:22]([CH3:42])[C:23]2[CH:24]=[N:25][C:26]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:21])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1>C(Cl)(Cl)(Cl)Cl.O.O.[Ru](=O)=O>[F:46][C:8]([F:7])([F:45])[C:9]1[CH:10]=[C:11]([C:19]([CH3:44])([CH3:43])[C:20]([N:22]([CH3:42])[C:23]2[CH:24]=[N:25][C:26]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][C:37]3=[O:2])=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:21])[CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=1

Participants

6

Reactant 2

HCID 6450815BefetupitantHCID 23667635Sodium periodate

Product 1

HCID 10144852HCID 10144852, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled suspension of 1.2 g (7.1 mmol) ruthenium(IV)oxide hydrate in a mixture of 50 ml carbon tetrachloride and 50 ml water were added 9.0 g (42 mmol) sodium periodate. After stirring for 30 min the organic layer was separated and the aqueous layer was extracted twice with 10-ml portions of carbon tetrachloride. The combined organic layers were filtered over celite, cooled to 0° C. and were added slowly to an ice-cooled solution of 2.0 g (3.54 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide in 20 ml carbon tetrachloride. The mixture was stirred for additional 15 min at 0° C., was filtered over celite and was evaporated. The residue was purified by flash-chromatography and gave 704 mg (34%) of the title compound as colourless foam. MS m/e (%): 580 (M+H+, 100).

Workup

  1. customwas separated
  2. extractionthe aqueous layer was extracted twice with 10-ml portions of carbon tetrachloride
  3. filtrationThe combined organic layers were filtered over celite
  4. additionwere added slowly to an ice-
  5. stirringThe mixture was stirred for additional 15 min at 0° C.
  6. filtrationwas filtered over celite
  7. customwas evaporated
  8. customThe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-75d504aa9d4244a49c8318d20cfa1890
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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