Potassium Carbonate → 6-{4-[Methyl(2-trifluoromethylphenyl)amino]piperidin-1-YL}pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Piperidinamine, N-methyl-N-[2-(trifluoromethyl)phenyl]-	HCID 57874421	—
Reactant	6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide	HCID 65561565	—
Catalyst	Tetrabutylammonium Iodide	HCID 67553	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-{4-[Methyl(2-trifluoromethylphenyl)amino]piperidin-1-YL}pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide	HCID 11712020	60%

Reaction Steps

A mixture of methylpiperidin-4-yl-(2-trifluoromethylphenyl)amine (0.130 g, 0.500 mmol), 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.113 g, 0.500 mmol), K2CO3 (0.100 g, 0.720 mmol) and n-Bu4NI (10 mg) in dioxane (10 mL) was heated to reflux overnight, then concentrated and purified by column chromatography to afford the title compound in 60% yield (0.147 g). 1H NMR (300 MHz, CDCl3) δ 8.30-8.26 (m, 1H), 8.10-7.95 (m, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.55-7.34 (m, 2H), 7.28 (d, J=7.8 Hz, 1H), 4.51 (s, br, 2H), 3.83-3.28 (m, 5H), 2.67 (s, 3H), 2.07-1.98 (m, 2H), 1.77 (s, br, 2H), 1.51-1.44 (m, 2H), 0.68-0.66 (m, 1H), 0.47-0.38 (m, 2H), 0.07-0.03 (m, 2H). MS (ES+) m/z 448.4 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07951805B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-4cc89a65a1b74b569bef3e8cfba27318
Source note	uspto-grants-2011_05