Diisopropylethylamine → N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide

https://huagongshe.com/de/reaction/1055992

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	2-Chloropyridine-3,4-diamine	HCID 285736	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	2-Phenoxyquinoline-8-carboxylic acid	HCID 89782088	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide	HCID 89782020	—
Produkt	N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide	HCID 89782144	—

Reaktionsschritte

A mixture of 2-phenoxyquinoline-8-carboxylic acid (119 mg, 0.449 mmol), 2-chloropyridine-3,4-diamine (97 mg, 0.673 mmol, Waterstone Technology, Carmel, Ind.), HATU (341 mg, 0.897 mmol), and DIPEA (235 μl, 1.346 mmol) in DMF (449 μl) was stirred at RT for 2 h. The mixture was diluted with EtOAc (100 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (3×75 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica chromatography (100% DCM to 5% MeOH/DCM) provided N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide (or N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide; regioisomer not determined; 178d, 49% yield). MS (ESI, pos. ion) m/z: 391.2 (M+1).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09394297B2
Quelldatensatz	uspto-grants-2016_07
ORD ID	ord-8ac49400164d4853ab290c11952e5d11
Quellennotiz	uspto-grants-2016_07