Dichloromethane → (RS)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-oxo-2lambda4-[1,2,3]oxathiazolidin-3-yl)-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1951743Notes

Reaction equation

HRID 1951743 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:13]([CH3:36])([CH3:35])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:31][CH2:32][CH2:33][OH:34])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClCCl.C(N(CC)CC)C.[S:49](Cl)(Cl)=[O:50]>O>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([C:13]([CH3:35])([CH3:36])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:31]3[CH2:32][CH2:33][O:34][S:49]3=[O:50])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 103030992-(3,5-bis(trifluoromethyl)phenyl)-N-(4-(2-chlorophenyl)-6-(2-hydroxyethylamino)pyridin-3-yl)-N,2-dimethylpropanamide

Product 1

HCID 86597718(RS)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-oxo-2lambda4-[1,2,3]oxathiazolidin-3-yl)-pyridin-3-yl]-N-methyl-isobutyramideYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.20 g (0.36 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-hydroxy-ethylamino)-pyridin-3-yl]-N-methyl-isobutyramide in a 5 ml dichloromethane were added consecutively 0.11 g (1.1 mmol) triethylamine and 0.05 g (0.4 mmol) thionyl chloride at room temperature. After 1 h the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.17 g (77%) of the title compound as a white solid.

Workup

  1. extractionextracted with three portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e6fc26eadcb4f8c8f1d5ce10c9130d3
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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