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

HRID 1925105Notes

Reaction equation

HRID 1925105 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([NH:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])=O.P([O-])([O-])(O)=O.[K+].[K+]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 24450Potassium Phosphate, DibasicHCID 59233013N-(2-bromoacetyl)cyclopropanecarboxamide

Product 1

HCID 59232980N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6-Chloropyridazin-3-amine, N-(2-bromoacetyl)cyclopropanecarboxamide, and potassium hydrogenphosphate were mixed in DMA at 75° C. to provide N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide. N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide was reacted with [1,2,4]triazolo[4,3-a]pyridine-3-thiol and K2CO3 in DMA at 145° C. and 100 psi N2 to provide N-(6-([1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclo-propanecarboxamide.

Sources & evidence

ORD record
ord-c69b953895964050a1097aa78876eab9
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

Loading…