2-Methoxyethylamine → N-((3-(3-(imidazo[1,2-b]pyridazin-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)-2-methoxyethanamine

HRID 251811Notes

Reaction equation

HRID 251811 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[N:18][N:17]4[CH:22]=3)[CH:11]=[CH:12][CH:13]=2)[N:4]=1.[CH3:23][O:24][CH2:25][CH2:26][NH2:27]>CCO>[N:15]1[C:14]([C:10]2[CH:9]=[C:8]([C:5]3[N:4]=[C:3]([CH2:2][NH:27][CH2:26][CH2:25][O:24][CH3:23])[O:7][N:6]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:22][N:17]2[C:16]=1[CH:21]=[CH:20][CH:19]=[N:18]2

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 576868302-(3-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine

Product 1

HCID 42624177N-((3-(3-(imidazo[1,2-b]pyridazin-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)-2-methoxyethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine(1.5 mmol), sodium iodide(cat.) and 2-methoxyethanamine(3 mmol) in 25 mL EtOH was stirred under reflux for 2 h. The mixture was concentrated in vacuo and the crude product was purified by column chromatography on silica gel to give the N-((3-(3-(imidazo[1,2-b]pyridazin-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)-2-methoxyethanamine.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4817779ba35a4a1d82fb15dc9a6bc9e0
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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