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

HRID 2203026
Notes
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Reaction equation

HRID 2203026 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[CH: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)[N: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[CH: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)[N: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 896902906-Bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazine

Product 1

HCID 89690368
4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-b]pyridazin-6-yl)pyridin-2(1H)-one
Yield 28%

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 (108 mg), 6-bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazine (150 mg), N,N′-dimethyl-1,2-ethanediamine (81 mg), CuI (87 mg), potassium carbonate (190 mg) and DMSO (3 ml) was heated at 150° C. for 1 h under microwave irradiation. The mixture was poured into 28% NH3 solution, 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), followed by crystalization from EtOAc-hexane to give the title compound (52.3 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)
  7. customfollowed by crystalization from EtOAc-hexane

Sources & evidence

ORD record
ord-7029be4f1acd4b589352e7051ad47a34
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