1-Hydroxybenzotriazole → HCID 118148694, compound

HRID 2201348Notes

Reaction equation

HRID 2201348 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[Cl:14][C:15]1[C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=[C:17]([C:24]([F:27])([F:26])[F:25])[N:16]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.N1C=CC=CC=1>[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:21]([C:20]2[C:15]([Cl:14])=[N:16][C:17]([C:24]([F:27])([F:25])[F:26])=[CH:18][CH:19]=2)=[O:22])=[CH:7][C:6]([C:10]([F:13])([F:11])[F:12])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 118148694HCID 118148694, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 0.42 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.50 g of 2-chloro-6-trifluoromethylpyridine-3-carboxylic acid, 0.64 g of EDCI hydrochloride, 30 mg of HOBt and 2.5 ml of pyridine was stirred at room temperature for 7 hours. Water was poured to the reaction mixture, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane, and then dried to obtain 0.81 g of 2-chloro-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide. 2-Chloro-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide

Workup

  1. filtrationthe precipitated solid was filtered
  2. washThe resulting solid was washed with water and n-hexane
  3. customdried

Sources & evidence

ORD record
ord-0b54445aee194df79e22b728776802c8
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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