Carbon Tetrachloride → HCID 9850206, compound

HRID 1168330Notes

Reaction equation

HRID 1168330 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. MS m/e (%): 540 (M+H+, 100).

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-2a52d89807014dd79c89c955e7fa370e
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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