Triethylamine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

HRID 69150

Reaction equation

HRID 69150 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[CH:9]N(C)C)=[CH:4][CH:3]=1.Br[CH2:14][C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2)=[O:16].C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:14]([C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)=[O:16])=[CH:9][N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6802247[2-(6-Chloro-3-pyridazinyl)-2-azavinyl]dimethylamineHCID 716996922-Bromo-1-(quinolin-6-yl)ethan-1-one

Product 1

HCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N′-(6-chloro-pyridazin-3-yl)-N,N-dimethyl-formamidine (Stage 1.6, 2 g, 10.8 mmol), 2-bromo-1-quinolin-6-yl-ethanone (Stage 1.3, 3.36 g, 10.8 mmol) and triethylamine (1.1 g, 10.8 mmol) was stirred under reflux for 90 min. The reaction was allowed to cool and water (100 mL) was then added. The resulting red precipitate was filtered off to afford the title compound as a red solid (tR 1.2 min(conditions 1), MH+=309).

Workup

  1. temperatureunder reflux for 90 min
  2. temperatureto cool
  3. filtrationThe resulting red precipitate was filtered off

Sources & evidence

ORD record
ord-a3c3b3b4a60845de82fab6907bdca040
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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