1-Hydroxybenzotriazole → HCID 72696793, compound

HRID 1052924Notes

Reaction equation

HRID 1052924 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.[CH2:12]([S:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18])[CH3:13].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH2:12]([S:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]=1)=[O:18])[CH3:13]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 516892Sodium BicarbonateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 72696793HCID 72696793, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.81 g of 2-amino-5-trifluoromethylpyridine, 0.91 g of 2-ethylsulfanyl-benzoic 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 added to the cooled reaction mixture, and the precipitated solid was taken by filtration and washed with acetonitrile to obtain 0.60 g of 2-ethylsulfanyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide.

Workup

  1. filtrationthe precipitated solid was taken by filtration
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-79dbcce8bd21424a92314aa74c4c4e72
Source dataset
uspto-grants-2016_07
Patent number
US09392791B2

Reaction notes

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