Diisopropylethylamine → N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(4-Aminophenyl)-5-bromopyridin-2-amine	HCID 68288976	—
Reactant	(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate	HCID 75951468	—
Reactant	1-(2-Fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid	HCID 86700060	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide	HCID 86700059	81.2%

Reaction Steps

DIPEA (114 μl) was added to a solution of the compound obtained in Step 2 of Example 8 (91 mg) and COMU (181 mg) in DMF (2.0 ml) at room temperature, and the mixture was stirred for 20 minutes. The compound obtained in Step 1 of Example 1 (95 mg) was added at room temperature. The mixture was stirred for six hours, followed by the addition of water. After extraction with ethyl acetate, the organic layer was washed with brine and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->30:1 (v/v)] to give 139 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-ab457a7f35314049ad14cc0f5086d06e
Source note	uspto-grants-2015_01