Befetupitant → HCID 10144852, compound

HRID 1835318Notes

Reaction equation

HRID 1835318 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 (7.12 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.

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-aeaa67a446fc4d2da045cb1bc89ee47b
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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