Water → HCID 68685023, compound

HRID 1865468Notes

Reaction equation

HRID 1865468 reaction equation
[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:13][CH2:12][C:11]([CH2:18][NH:19][C:20](=[O:33])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[N:23][C:22]=3SC)([CH2:14][CH:15]3[CH2:17][CH2:16]3)[CH2:10][CH2:9]2)(=O)=[O:6])[CH2:3][CH2:2]1.O[O:35][S:36]([O-:38])=O.[K+].[C:40](=O)([O-])O.[Na+].[OH2:45]>CC(C)=O>[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:9][CH2:10][C:11]([CH2:18][NH:19][C:20](=[O:33])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[N:23][C:22]=3[S:36]([CH3:40])(=[O:38])=[O:35])([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:12][CH2:13]2)(=[O:6])=[O:45])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68681210HCID 68681210, compound

Product 1

HCID 68685023HCID 68685023, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-(4-cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohexylmethyl)-2-methylsulfanyl-6-trifluoromethylnicotinamide (44 mg, 0.087 mmol) in acetone (2 ml) was treated with a solution of oxone (161 mg, 0.26 mmol) in water (2 ml) and the mixture heated under reflux for 2 hours. The mixture was allowed to cool to ambient temperature and the pH of the mixture adjusted to 7 by the addition of saturated sodium hydrogen carbonate solution. The mixture was diluted with water (5 ml) and extracted with dichloromethane (5 ml). The mixture was separated using a 5 micron PTFE frit and the filtrate was evaporated. The colourless oil was purified by preparative plate chromatography on silica eluting with 10% ethyl acetate in dichloromethane. Collecting the appropriate band, trituration of the silica with ethyl acetate, filtration and evaporation gave a white foam (36 mg, 80%). 1H NMR δ (ppm)(CDCl3): 8.47 (1H, d, J=8.0 Hz), 7.98 (1H, d, J=8.0 Hz), 7.06 (1H, s), 3.65 (2H, d, J=6.0 Hz), 3.48 (3H, s), 2.94-2.89 (3H, m), 2.06-1.91 (6H, m), 1.41-1.35 (2H, m), 1.30 (2H, d, J=6.7 Hz), 1.22-1.15 (1H, m), 0.76-0.66 (3H, m), 0.49-0.41 (4H, m), 0.07 (2H, q, J=4.9 Hz). MS (m/e)=5.37.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with dichloromethane (5 ml)
  4. customThe mixture was separated
  5. customthe filtrate was evaporated
  6. customThe colourless oil was purified by preparative plate chromatography on silica eluting with 10% ethyl acetate in dichloromethane
  7. customCollecting the appropriate band, trituration of the silica
  8. filtrationwith ethyl acetate, filtration and evaporation

Sources & evidence

ORD record
ord-9cc888585af6400faad6885d7c1d1d38
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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