Diisopropylethylamine → 2-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	6-(Morpholin-4-ylmethyl)pyridin-2-amine	HCID 12077809	—
Reactant	2-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid	HCID 58154611	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamide	HCID 58154657	22%

Reaction Steps

2-(5-methylpyridin-3-yl)quinoline-8-carboxylic acid (0.135 g, 0.51 mmol) was combined with DIPEA (0.140 mL, 0.811 mmol) and HATU (0.200 g, 0.51 mmol) in DMF (5 mL). The mixture was stirred at room temperature for ten minutes, at which time 6-(morpholinomethyl)pyridin-2-amine (0.090 g, 0.466 mmol) was added. The mixture was stirred 18 hours, and then water (10 mL) was added. The resulting precipitate was collected by filtration, and the solids were triturated in methanol to obtain 2-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamide as a tan solid (0.045 g, 22% yield. MS (ESI) calcd for C26H25N5O2 (m/z): 439.20. found: 440 [M+1].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08685970B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-b3503837a4ce401cb3b63c8de76added
Source note	uspto-grants-2014_04