Water → N-{1-[1-(2,4-dichlorophenyl)cyclopropyl]ethyl}-2-chloropyrazine-3-carboxamide

HRID 389175Notes

Reaction equation

HRID 389175 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[N:6][CH:5]=[CH:4][N:3]=1.Cl.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH:23]([NH2:25])[CH3:24])[CH2:22][CH2:21]1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH:23]([NH:25][C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][N:6]=2)=[O:10])[CH3:24])[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 15019003-Chloro-2-pyrazine-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672229921-[1-(2,4-Dichlorophenyl)cyclopropyl]ethylamine hydrochloride

Product 1

HCID 86654185N-{1-[1-(2,4-dichlorophenyl)cyclopropyl]ethyl}-2-chloropyrazine-3-carboxamideYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-chloropyrazine-3-carboxylic acid (0.15 g, 1.0 mmol), 1-[1-(2,4-dichlorophenyl)cyclopropyl]ethylamine hydrochloride (0.25 g, 0.94 mmol) and 4-dimethylaminopyridine (0.29 g, 2.4 mmol) in chloroform (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.22 g, 1.2 mmol) and the mixture was stirred at room temperature for 12 hrs. After adding water and chloroform, the mixture was separated, 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=3:1) to give a desired compound (yield; 0.24 g, 69%).

Workup

  1. customthe mixture was separated
  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=3:1)

Sources & evidence

ORD record
ord-d85b52312e4242fe9327a6178011d746
Source dataset
uspto-grants-2013_02
Patent number
US08378114B2

Reaction notes

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