Diisopropylethylamine → HCID 86700030, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
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	5-(4-Fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid	HCID 60204212	—
Reactant	HCID 86700031	HCID 86700031	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86700030	HCID 86700030	20.2%

Reaction Steps

HOAt (23 mg), HATU (97 mg), DMAP (10 mg) and DIPEA (50 μl) were added to a solution of 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid (46 mg) in DMF (1 ml) at room temperature. The reaction mixture was stirred at room temperature for three hours. The compound obtained in Step 2 of Example 1 (55 mg) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified by PLC [ethyl acetate:methanol=20:1 (v/v)] to give 19 mg of the title compound as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08933103B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-1becf47f132e4710b3dffbef92656926
Source note	uspto-grants-2015_01