Carbon Tetrachloride → HCID 9850206, compound

HRID 1369153Notes

Reaction equation

HRID 1369153 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]3CC[O:33][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.I([O-])(=O)(=O)=O.[Na+].C(Cl)(Cl)(Cl)Cl.C(#N)C>O.[Ru](Cl)(Cl)Cl.ClCCl.O>[F:39][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:37])([CH3:38])[C:14]([N:16]([C:17]2[CH:18]=[N:19][C:20]([NH:30][CH2:31][CH2:32][OH:33])=[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:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 6450815BefetupitantHCID 23667635Sodium periodate

Product 1

HCID 9850206HCID 9850206, compoundYield 37.1%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g (1.76 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide, 100 mg (0.48 mmol) ruthenium(III)chloride hydrate, 832 mg (3.87 mmol) sodium periodate, 3.5 ml carbon tetrachloride, 3.5 ml acetonitrile and 5.3 ml water was stirred for 4 days at room temperature. Dichloromethane was added, the organic layer was separated, washed with sodium hydrogensulfite solution and filtered over celite. To the filtrate were added 10 ml 1 N potassium hydroxide solution and 20 ml methanol. After heating the mixture for 1 h at 40° C., the solvents were removed in vacuo and the residue was purified by flash-chromatography to give 352 mg (37%) of the title compound as light brown foam.

Workup

  1. customthe organic layer was separated
  2. washwashed with sodium hydrogensulfite solution
  3. filtrationfiltered over celite
  4. additionTo the filtrate were added 10 ml 1 N potassium hydroxide solution and 20 ml methanol
  5. temperatureAfter heating the mixture for 1 h at 40° C.
  6. customthe solvents were removed in vacuo
  7. customthe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-dedb3492d164404aae5443eeab49d44f
Source dataset
uspto-grants-2003_06
Patent number
US06576762B2

Reaction notes

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