Pyridine → HCID 118148713, compound

HRID 2201365Notes

Reaction equation

HRID 2201365 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]=[CH:19][N:18]=1)[CH3:15].CCN=C=NCCCN(C)C.Cl.N1C=CC=CC=1>C1C=CC2N(O)N=NC=2C=1.O>[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:23]([C:22]2[C:17]([S:16][CH2:14][CH3:15])=[N:18][CH:19]=[N:20][CH:21]=2)=[O:24])=[CH:7][C:6]([C:10]([F:13])([F:11])[F:12])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 1179889234-Ethylsulfanylpyrimidine-5-carboxylic acid

Product 1

HCID 118148713HCID 118148713, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.04 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 1.00 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid, 1.57 g of EDCI hydrochloride, 73 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, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.94 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide. 4-Ethylsulfanylpyrimidine-5-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-8d5183925ffd47aa93890955e8b5d4e1
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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