Triethylamine → N,N-dimethyl-3-(4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)pyridin-3-yl)prop-2-yn-1-amine

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Triethylamine	HCID 8471	—
Edukt	N,N-Dimethylpropargylamine	HCID 81643	—
Edukt	3-((3-Iodopyridin-4-yloxy)methyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine	HCID 57691157	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	HCID 178418397	HCID 178418397	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Produkt	N,N-dimethyl-3-(4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)pyridin-3-yl)prop-2-yn-1-amine	HCID 57691024	—

Reaktionsbedingungen

Temperatur	75 °C

Reaktionsschritte

Tetrakis(triphenylphosphine)palladium(0) (14.4 mg, 12.5 μmol) was added to a suspension of 3-((3-iodopyridin-4-yloxy)methyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine (107 mg, 249 μmol) and 1-dimethylamino-2-propyne (80.4 μl, 748 μmol) in THF (0.6 mL) and triethylamine (591 μl, 4238 μmol) at RT. Copper(i) iodide, 99.999% (4.75 mg, 24.9 μmol) was added and the reaction mixture was stirred at 75° C. (oil bath) for ˜75 min. The reaction mixture was cooled at RT, concentrated in vacuo. Purification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 90/10) afforded the title compound. MS m/z=385.1 [M+H]+. Calc'd for C, 22; H, 20; N, 6; O, : 384.44

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08217177B2
Quelldatensatz	uspto-grants-2012_07
ORD ID	ord-42411ee82bee41fc9f0e9be6f823c673
Quellennotiz	uspto-grants-2012_07