p-Toluenesulfonic acid → 2-Chloro-6-[5-ethyl-2-(2-pyridyl)oxazolidin-3-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile

HRID 1911822Notes

Reaction equation

HRID 1911822 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[C:12]([NH:22][CH2:23][CH:24](O)[CH2:25][CH3:26])[N:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=[C:12]([N:22]2[CH2:23][CH:24]([CH2:25][CH3:26])[O:8][CH:7]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 142732-PyridinecarboxaldehydeHCID 866534212-Chloro-6-(2-hydroxybutylamino)-4-(trifluoromethyl)pyridine-3-carbonitrile

Product 1

HCID 582650782-Chloro-6-[5-ethyl-2-(2-pyridyl)oxazolidin-3-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyridine-2-carboxaldehyde (207 mg, 1.9 mmol) was added to a toluene solution (15 mL) of 2-chloro-6-(2-hydroxybutylamino)-4-(trifluoromethyl)pyridine-3-carbonitrile (400 mg, 1.3 mmol) followed by a catalytic amount of para-toluene sulfonic acid (50 mg). The reactants were refluxed for 6 hours in a Dean-Stark apparatus, concentrated under reduced pressure, adsorbed onto silica and purified using a neutral alumina column, eluting with a mobile phase of 10% ethyl acetate in hexane. 2-Chloro-6-[5-ethyl-2-(2-pyridyl)oxazolidin-3-yl]-4-(trifluoromethyl) pyridine-3-carbonitrile (Compound 17) was isolated as a solid in 37% yield. mp 115-118° C.

Workup

  1. temperatureThe reactants were refluxed for 6 hours in a Dean-Stark apparatus
  2. concentrationconcentrated under reduced pressure
  3. custompurified
  4. washeluting with a mobile phase of 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0cc0408ca7624127a01f1e9ce7820c06
Source dataset
uspto-grants-2013_12
Patent number
US08604199B2

Reaction notes

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