1-Methylpiperidine-4-methylamine → 7-Methyl-N-((1-methylpiperidin-4-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)-imidazo[1,2-b]pyridazin-6-amine

Participants

Role	Name	HCID	Charge
Reactant	1-Methylpiperidine-4-methylamine	HCID 81574	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	6-Chloro-7-methyl-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine	HCID 59380263	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	7-Methyl-N-((1-methylpiperidin-4-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)-imidazo[1,2-b]pyridazin-6-amine	HCID 25025644	7.3%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To the toluene (5 mL) solvent was added Compound 11 (57 mg, 0.174 mmol), (1-methylpiperidine-4-yl)methanamine 17 (26.8 mg, 0.209 mmol), ligand (10.27 mg, 0.026 mmol), NaOtBu (23.40 mg, 0.244 mmol) and Pd2(dba)3 (11.95, 0.013 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated with microwave at 150° C. for 1 h. Concentration and preparative TLC (10% MeOH/DCM) afforded 5.3 mg (7.26%) of Compound 7-37.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08710057B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-1c77331032204ecbab41b6cf54562b77
Source note	uspto-grants-2014_04