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Ammonia → 4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyrazin-6-yl)pyridin-2(1H)-one

HRID 2203017
Notes
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Reaction equation

HRID 2203017 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[N:19]=[CH:20][C:21]2[N:22]([C:24]([CH3:30])=[C:25]([CH:27]3[CH2:29][CH2:28]3)[N:26]=2)[CH:23]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>[Cu]I.CS(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[N:19]=[CH:20][C:21]4[N:22]([C:24]([CH3:30])=[C:25]([CH:27]5[CH2:29][CH2:28]5)[N:26]=4)[CH:23]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 896903556-Bromo-2-cyclopropyl-3-methylimidazo[1,2-a]pyrazine

Product 1

HCID 89691416
4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyrazin-6-yl)pyridin-2(1H)-one
Yield 42.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (26.2 mg), 6-bromo-2-cyclopropyl-3-methylimidazo[1,2-a]pyrazine (42.1 mg), N,N′-dimethyl-1,2-ethanediamine (19.63 mg), CuI (21.2 mg), potassium carbonate (46.2 mg) and DMSO (1 ml) was heated at 150° C. for 1 h under microwave irradiation. The mixture was poured into 28% NH3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc) to give the title compound (19.1 mg) as pale yellow crystals.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-4b0c648af6c746bb8a8f103e6087762e
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365540B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes