Citric Acid → 3-Ethylsulfanyl pyridin-2-carboxylic acid [2-(2,2,2-trifluoroethyl)amino-5-trifluoromethylpyridin-3-yl]amide

HRID 2273331

Reaction equation

HRID 2273331 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][NH:4][C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1.[CH2:18]([S:20][C:21]1[C:22]([C:27](O)=[O:28])=[N:23][CH:24]=[CH:25][CH:26]=1)[CH3:19].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[F:17][C:2]([F:1])([F:16])[CH2:3][NH:4][C:5]1[C:10]([NH:11][C:27]([C:22]2[C:21]([S:20][CH2:18][CH3:19])=[CH:26][CH:25]=[CH:24][N:23]=2)=[O:28])=[CH:9][C:8]([C:12]([F:13])([F:14])[F:15])=[CH:7][N:6]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acidHCID 86725179N2-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridine-2,3-diamine

Product 1

HCID 903242123-Ethylsulfanyl pyridin-2-carboxylic acid [2-(2,2,2-trifluoroethyl)amino-5-trifluoromethylpyridin-3-yl]amideYield 88.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N2-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine (0.52 g), 3-ethylsulfanylpyridin-2-carboxylic acid (0.37 g), WSC (0.46 g), HOBt (27 mg) and pyridine (2 ml) was stirred at room temperature for 3 hours. To the reaction mixture was poured aqueous 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give 3-ethylsulfanyl pyridin-2-carboxylic acid [2-(2,2,2-trifluoroethyl)amino-5-trifluoromethylpyridin-3-yl]amide (0.75 g), which is hereinafter referred to as “intermediate compound (M3-43)”.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1225677c803d42a09aad29db42533660
Source dataset
uspto-grants-2015_09
Patent number
US09120823B2

Linked notes

Loading…