Cyclopropanecarbonyl chloride → N-{3-[(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamide

HRID 2391176Notes

Reaction equation

HRID 2391176 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[N:14]=2)[N:11]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>CN(C)C(=O)C>[C:16]([NH:15][C:13]1[N:14]=[C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:25]([CH:22]4[CH2:24][CH2:23]4)=[O:26])[CH:21]=[CH:20][CH:19]=3)=[N:11][N:10]2[CH:12]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57441053N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide

Product 1

HCID 57505442N-{3-[(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide (17 mg, 0.06 mmol), cyclopropanecarbonyl chloride (9.5 mg, 0.09 mmol) and N,N-dimethylacetamide (0.5 mL) was stirred at room temperature for 14 hr. The reaction mixture was purified by preparative HPLC to give the title compound (10.8 mg, 51%).

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-42a666ae556d462b9a7a3d17aeb7e7df
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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