Water → HCID 86682692, compound

HRID 1755283Notes

Reaction equation

HRID 1755283 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[C:15]1[C:16]2[N:17]([CH:22]=[CH:23][N:24]=2)[N:18]=[C:19]([Cl:21])[CH:20]=1.O>CN(C=O)C>[Cl:21][C:19]1[CH:20]=[C:15]([NH:9][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:10])[F:11])[N:8]=2)[C:16]2[N:17]([CH:22]=[CH:23][N:24]=2)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8210242-Amino-6-(trifluoromethyl)pyridineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86682692HCID 86682692, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(trifluoromethyl)pyridin-2-amine (0.668 g, 4.12 mmol) in DMF (5 mL) was added NaH (0.10 g, 4.18 mmol) and stirred for 0.5 h. To the mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.38 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h then 100 mL of water was added and the precipitate collected by filtration and washed with water to give 6-chloro-N-(6-(trifluoromethyl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.513 g, 99%) as a light brown solid. LC-MS: [M+H]+, 314.1, tR=1.738 min.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-b0306fdd73174d22a334db910cb0db61
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

Loading…