Diethylethanolamine → HCID 58879980, compound

Participants

Role	Name	HCID	Charge
Reactant	Diethylethanolamine	HCID 7497	—
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	HCID 58879956	HCID 58879956	—
Reactant	3-amino-1-(4-fluorophenyl)pyridin-2(1H)-one	HCID 58879972	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 58879980	HCID 58879980	57%

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 4-(2-carbamoylpyridin-4-yloxy)-3-fluorobenzoic acid (0.3 mmol, 83 mg) in DMF (2 mL), were added HATU (Perspective Biosystems, 0.45 mmol, 171 mg), 3-amino-1-(4-fluorophenyl)pyridin-2(1H)-one (0.3 mmol, 61.2 mg) and DEEA (Aldrich, 0.2 mL). The reaction mixture were heated at 50° C. for 5 h. After cooling to room temperature, 5 mL of methanol was added. The product was purified by preparative HPLC. The desired fractions were combined, neutralized to pH 7-8 with aq. K2HPO4, and concentrated in vacuo. The precipitate that formed was collected by filtration, rinsed with water, and dried under vacuum to give the desired product (78 mg, 57% yield). MS(ESf+) m/z 463.25 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07880004B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-ecdfdf6fdb3e451dbf7821a3bb60bcd1
Source note	uspto-grants-2011_02