2-Amino-5-chloropyrazine → 6-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine

HRID 539794Notes

Reaction equation

HRID 539794 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1)=O>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=3)[N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 128084192-Amino-5-chloropyrazineHCID 575162692-Bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 575162776-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloropyrazin-2-amine (0.336 g, 2.6 mmol) and 2-bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone (0.811 g, 2.6 mmol) in acetonitrile (15 mL) is stirred at 100° C. for 18 hr. The mixture is concentrated to give the title compound (890 mg), which is used without further purification. LCMS m/z=343.3 [M+H]+, tR=2.65 min.

Workup

  1. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-91dbc166b06c4c8bbb6c1f6bfe7b21bc
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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