Sodium Bicarbonate → 3-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide

HRID 713655Notes

Reaction equation

HRID 713655 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH2:13]([S:15][C:16]1[C:17]([C:22](O)=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14].CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>C1C=CC2N(O)N=NC=2C=1.N1C=CC=CC=1>[CH2:13]([S:15][C:16]1[C:17]([C:22]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 790069543-(Ethylsulfanyl)pyridine-2-carboxylic acid

Product 1

HCID 1181133323-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamideYield 89.2%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 0.35 g of 4-trifluoromethoxyaniline, 0.36 g of 3-ethylsulfanylpicolinic acid, 0.46 g of EDCI hydrochloride, 0.02 g of HOBt and 3 mL of pyridine was stirred at room temperature overnight. 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 solid was washed with hexane and dried to obtain 0.60 g of 3-ethylsulfanyl-N-(4-trifluoromethoxyphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 18).

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
  4. washthe resulting solid was washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-8bf246cef7684967ad24936a9495a887
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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