1-Hydroxybenzotriazole → HCID 118148696, compound

HRID 2201353Notes

Reaction equation

HRID 2201353 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[N:18]([C:23](O)=O)NC=[CH:21][CH:22]=1)[CH3:15].CCN=C=NCCC[N:34]([CH3:36])C.Cl.C1C=CC2N([OH:47])N=NC=2C=1>O.N1C=CC=CC=1>[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:21]([C:22]2[C:17]([S:16][CH2:14][CH3:15])=[N:18][CH:23]=[CH:36][N:34]=2)=[O:47])=[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 117988971HCID 117988971, compound

Product 1

HCID 118148696HCID 118148696, compoundYield 966.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 618 mg of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 612 mg of 3-ethylsulfanylpyridazine-2-carboxylic acid, 958 mg of EDCI hydrochloride, 45 mg of HOBt and 5 ml of pyridine was stirred at 60° C. for 4 hours. Water was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.15 g of 3-ethylsulfanylpyrazine-2-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide. 3-Ethylsulfanylpyrazine-2-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e3e398ff6b04da2914e8f913d7e9600
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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