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1-Hydroxybenzotriazole → 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

HRID 713657
Notes
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Reaction equation

HRID 713657 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1.[CH2:13]([S:15][C:16]1[C:17]([C:26]([OH:28])=O)=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH3:14].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH2:13]([S:15][C:16]1[C:17]([C:26]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:11])([F:10])[F:12])=[CH:5][N:4]=2)=[O:28])=[N:18][CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1)[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18526206N-Methyl-5-(trifluoromethyl)pyridin-2-amineHCID 712468933-Ethylsulfanyl-5-trifluoromethylpicolinic acid

Product 1

HCID 118113423
3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide
Yield 22.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.35 g of 2-methylamino-5-trifluoromethylpyridine, 0.50 g of 3-ethylsulfanyl-5-trifluoromethylpicolinic acid, 0.46 g of EDCI hydrochloride, 0.02 g of HOBt and 3 mL of pyridine was stirred at room temperature for 3 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 0.18 g of 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 24).

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-458a5450666b49328c77ae9d77320c27
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09185910B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes