Triethylamine → 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine

https://huagongshe.com/de/reaction/40193

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Triethylamine	HCID 8471	—
Edukt	N,N-Dimethylpropargylamine	HCID 81643	—
Edukt	4-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline	HCID 25066992	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	HCID 178418476	HCID 178418476	—
Lösungsmittel	Acetonitrile	HCID 6342	—
Produkt	Ammonium hydroxide methanol	HCID 21894508	—
Produkt	3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine	HCID 25065341	34,3%

Reaktionsbedingungen

Temperatur	80 °C

Reaktionsschritte

In a 10 mL sealed tube under N2 were dissolved dichlorobis(triphenylphosphine)palladium (41 mg, 59 μmol), N,N-dimethylprop-2-yn-1-amine (97 mg, 1170 μmol), 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (prepared according to General Method A) (200 mg, 585 μmol), TRIETHYLAMINE (1631 μl, 11704 μmol) and COPPER(I) IODIDE (11 mg, 59 μmol) in 3 mL of MeCN then stirred and heated at 80° C. for 10 h. The crude reaction mixture was directly purified by MPLC (ISCO) with DCM/DCM:MeOH:NH4OH (90:10:1) 95:5 to afforded 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine (26 mg, 11% yield) as a yellow solid. MS m/z=388.2 [M+1]+. Calc'd for C21H20N6O2: 389.2.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08524900B2
Quelldatensatz	uspto-grants-2013_09
ORD ID	ord-f4f499cd32ac4fcfab6ed56c723b95ac
Quellennotiz	uspto-grants-2013_09