1-Hydroxybenzotriazole → HCID 118148693, compound

HRID 2201361Notes

Reaction equation

HRID 2201361 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.[CH2:14]([S:16][C:17]1[C:22]([C:23](O)=[O:24])=[CH:21][N:20]=[C:19]([C:26]([F:29])([F:28])[F:27])[CH:18]=1)[CH3:15].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:23]([C:22]2[CH:21]=[N:20][C:19]([C:26]([F:28])([F:29])[F:27])=[CH:18][C:17]=2[S:16][CH2:14][CH3:15])=[O:24])=[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 117988652HCID 117988652, compound

Product 1

HCID 118148693HCID 118148693, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 428 mg of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 562 mg of 4-ethylsulfanyl-6-trifluoromethylnicotinic acid, 645 mg of EDCI hydrochloride, 30 mg of HOBt and 2.5 ml of pyridine was stirred at room temperature for 5 hours, then allowed to stand at room temperature overnight. 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 786 mg of 4-ethylsulfanyl-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide. 4-Ethylsulfanyl-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide

Workup

  1. waitto stand at room temperature overnight
  2. filtrationthe precipitated solid was filtered
  3. washThe resulting solid was washed with water and n-hexane
  4. customdried

Sources & evidence

ORD record
ord-b65f71e6d3284ccba84b3f9a02c38dc8
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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