Diisopropylethylamine → 2-(4-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-quinolinecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	5-(Furan-2-yl)-1,3,4-oxadiazol-2-amine	HCID 202185	—
Reactant	2-(4-Fluorophenyl)quinoline-4-carboxylic acid	HCID 723163	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-quinolinecarboxamide	HCID 67204157	60%

Reaction Steps

Commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (57 mg, 0.38 mmol), HOAt (51 mg, 0.37 mmol), HATU (143 mg, 0.38 mmol), and N,N-diisopropylethylamine (87 μL, 0.50 mmol) were added to a DMF (2 mL) solution of commercially available 2-(4-fluorophenyl)-4-quinolinecarboxylic acid (67 mg, 0.25 mmol), and the mixture was stirred at room temperature for 3 days. To the reaction solution, water was added, and the deposited solid was collected by filtration, and washed with water and then with methanol and methylene chloride in this order. The obtained solid was dried to obtain the title compound (61 mg, 0.15 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08466290B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-4fb70990186948669737a7c83bc94597
Source note	uspto-grants-2013_06