1-Hydroxybenzotriazole → HCID 118148702, compound

HRID 2201356Notes

Reaction equation

HRID 2201356 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][N:18]=[CH:17][CH: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[CH:19]=[N:18][CH:17]=[CH:16][C:15]=2[Cl:14])=[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 8182294-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 118148702HCID 118148702, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 524 mg of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 500 mg of 4-chloronicotinic acid, 790 mg of EDCI hydrochloride, 37 mg of HOBt and 4 ml of pyridine was stirred at room temperature for 4 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 828 mg of 4-chloropyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide. 4-chloropyridine-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-2a8d13ec42b44f1c8145b8b3a424f800
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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