Thiazolidine → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiazolidin-3-yl-pyridin-3-yl]-N-methyl-isobutyramide

HRID 547822Notes

Reaction equation

HRID 547822 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>[OH-].[Na+]>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:39]3[CH2:40][CH2:41][S:37][CH2:38]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 10444ThiazolidineHCID 235027842-(3,5-Bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(4-fluoro-2-methylphenyl)pyrid-3-yl)-N,2-dimethylpropanamide

Product 1

HCID 117866102-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiazolidin-3-yl-pyridin-3-yl]-N-methyl-isobutyramideYield 12%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 0.25 g (0.47 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide and 0.59 g (6.6 mmol) thiazolidine was heated three times at 180° C. for 30 minutes and once at 250° C. for 15 minutes under microwave irradiation in a sealed tube. The reaction mixture was diluted with a 0.2 M aqueous solution of sodium hydroxide and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography and drying in high vacuo (70-90° C./1-2 mbar) for three hours gave 33 mg (12%) of the title compound as a yellow oil.

Workup

  1. customonce at 250° C. for 15 minutes under microwave irradiation in a sealed tube
  2. extractionextracted with three portions of tert-butyl methyl ether
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customFlash column chromatography and drying in high vacuo (70-90° C./1-2 mbar) for three hours

Sources & evidence

ORD record
ord-665589352c444dd29ddf952d02aa599e
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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