1-Hydroxybenzotriazole → HCID 118113275, compound

HRID 713635Notes

Reaction equation

HRID 713635 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[Cl:12][C:13]1[C:14]([C:23](O)=[O:24])=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:12][C:13]1[C:14]([C:23]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]=2)=[O:24])=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28219083-Chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid

Product 1

HCID 118113275HCID 118113275, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.81 g of 2-amino-5-trifluoromethylpyridine, 1.13 g of 3-chloro-5-trifluoromethylpicolinic acid, 1.15 g of EDCI hydrochloride, 0.06 g of HOBt and 10 mL of pyridine was stirred at 60° C. for 2 hours. A saturated aqueous sodium bicarbonate solution was poured to the cooled 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 1.35 g of 3-chloro-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide.

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-415f64c56635417ebdc44d85f543ddd1
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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