Water → N-[2-(2,4-dichlorophenyl)-1-methylethyl]-2-trifluoromethylpyrazine-3-carboxamide

HRID 389174Notes

Reaction equation

HRID 389174 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([OH:11])=O)=[N:7][CH:6]=[CH:5][N:4]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][CH:23]([NH2:25])[CH3:24].Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][CH:23]([NH:25][C:9]([C:8]1[C:3]([C:2]([F:1])([F:13])[F:12])=[N:4][CH:5]=[CH:6][N:7]=1)=[O:11])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30411751-(2,4-Dichlorophenyl)propan-2-amineHCID 536308603-(Trifluoromethyl)pyrazine-2-carboxylic acid

Product 1

HCID 16742597N-[2-(2,4-dichlorophenyl)-1-methylethyl]-2-trifluoromethylpyrazine-3-carboxamideYield 63.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-trifluoromethylpyrazine-3-carboxylic acid (0.25 g, 1.3 mmol), [2-(2,4-dichlorophenyl)-1-methylethyl]amine (0.27 g, 1.3 mmol) and 4-dimethylaminopyridine (0.19 g, 1.6 mmol) in chloroform (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.3 g, 1.6 mmol) and the mixture was stirred at room temperature for 12 hrs. After adding water and chloroform, the mixture was partitioned, and the organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give a desired compound (yield; 0.31 g, 63%).

Workup

  1. customthe mixture was partitioned
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0beea0ad785b46a28b366d3c0891ded1
Source dataset
uspto-grants-2013_02
Patent number
US08378114B2

Reaction notes

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