6-Amino-3-chloropyridazine → N-(3-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-5-cyanophenyl)methanesulfonamide

HRID 251830Notes

Reaction equation

HRID 251830 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)=O.[Cl:18][C:19]1[N:24]=[N:23][C:22]([NH2:25])=[CH:21][CH:20]=1>CCO>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([CH:2]=[C:3]([C:5]3[CH:6]=[C:7]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=[C:9]([C:11]#[N:12])[CH:10]=3)[N:25]=2)[N:24]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 57686827N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide

Product 1

HCID 57686797N-(3-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-5-cyanophenyl)methanesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide (0.8 mmol) and 6-chloropyridazin-3-amine (0.8 mmol) in EtOH (8 mL) was refluxed for 4 hours. After cooling, the resulting mixture was filtrated to give N-(3-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-5-cyanophenyl)methanesulfonamide in 50% yield. 10% Pd/C (20 mg) was added to the solution of N-(3-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-5-cyanophenyl)methanesulfonamide (0.3 mmol) in THF (25 mL. Then it was stirred at room temperature for 4 hours. After filtration, it was concentrated to give N-(3-cyano-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide in 95% yield.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting mixture was filtrated

Sources & evidence

ORD record
ord-34e8d54d11c9434c90117ff2bb0e9a93
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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