Cyclobutanecarbonyl chloride → N-[5-({2-[(cyclobutylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391404

Reaction equation

HRID 2391404 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:17]=3)=[N:7][N:6]2[CH:29]=1.[CH:30]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31]1>CN(C)C(=O)C>[CH:30]1([C:34]([NH:2][C:3]2[N:4]=[C:5]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([NH:18][C:19]([C:21]5[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=5)=[O:20])[CH:17]=4)=[N:7][N:6]3[CH:29]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 57505635N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride

Product 1

HCID 57505644N-[5-({2-[(cyclobutylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 264 and using N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (200 mg, 0.48 mmol), cyclobutanecarbonyl chloride (86 mg, 0.73 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (170 mg, 76%) was obtained as a white solid.

Sources & evidence

ORD record
ord-104c4f399be3484f83a862d5e8f07247
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Linked notes

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