Diisopropylethylamine → Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methyl 6-chloropyridine-3-carboxylate	HCID 254249	—
Reactant	C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamine	HCID 66643513	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate	HCID 66643788	49%

Reaction Conditions

Temperature	160 °C

Reaction Steps

C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamine (320 mg, 1.90 mmol) was dissolved in DMSO (3 mL), methyl 6-chloronicotinate (326 mg, 1.90 mmol) and N,N-diisopropylethylamine (492 mg, 3.80 mmol) added, and the reaction mixture heated under microwave irradiation at 160° C. for 1 h. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (280 mg, 49%) as a white solid. MS: m/e=348.5 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08357703B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-b2a7866101834f60a0ce45dff2f8d23f
Source note	uspto-grants-2013_01