Tetrahydrofuran → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-3-methylisoxazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Oxalyl chloride	HCID 65578	—
Reactant	3-Methyl-1,2-oxazole-4-carboxylic acid	HCID 4589692	—
Reactant	N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide	HCID 57505446	—
Catalyst	Dimethylformamide	HCID 6228	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-3-methylisoxazole-4-carboxamide	HCID 57505539	65.5%

Reaction Steps

Using 3-methylisoxazole-4-carboxylic acid (127 mg, 1.0 mmol), N,N-dimethylformamide (2 drops), tetrahydrofuran (10 mL), oxalyl chloride (0.172 mL, 2.0 mmol), N-methylpyrrolidone (5 mL) and N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (164 mg, 0.50 mmol), and in the same manner as in Example 173, the title compound (143 mg, yield 65%) was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08044049B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-1118a891695843fba77de2f34c5a12b2
Source note	uspto-grants-2011_10