Sodium Bicarbonate → 3-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide

HRID 713665Notes

Reaction equation

HRID 713665 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)([O:6][CH3:7])[O:4][CH3:5].[CH2:17]([S:19][C:20]1[C:21]([C:26](O)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=1)[CH3:18].CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>C1C=CC2N(O)N=NC=2C=1.N1C=CC=CC=1>[CH2:17]([S:19][C:20]1[C:21]([C:26]([NH:12][C:11]2[CH:13]=[CH:14][C:8]([C:3]([O:6][CH3:7])([O:4][CH3:5])[C:2]([F:15])([F:16])[F:1])=[CH:9][CH:10]=2)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=1)[CH3:18]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acidHCID 1181134654-(2,2,2-Trifluoro-1,1-dimethoxyethyl)aniline

Product 1

HCID 1181134133-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamideYield 89.4%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 0.38 g of 4-(2,2,2-trifluoro-1,1-dimethoxyethyl)aniline, 0.22 g of 3-ethylsulfanylpicolinic acid, 0.29 g of EDCI hydrochloride, 0.01 g of HOBt and 5 mL of pyridine was stirred at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.43 g of 3-ethylsulfanyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide (Compound of Present Invention 58).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acc110fd4c104b7da7e5a3017d460713
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

Loading…