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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2095921Generated: October 30, 2026

Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(4-fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

https://huagongshe.com/reaction/2095921

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
ReactantN-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 58158605—
Reactant1-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 66968922—
SolventDimethylformamideHCID 6228—
ProductN-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(4-fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideHCID 5815855558.6%

Reaction Steps

A mixture of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.459 mmol), 1-(4-fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (151 mg, 0.551 mmol), HATU (262 mg, 0.689 mmol), N,N-diisopropylethylamine (240 μL, 1.37 mmol) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 4 days. After dilution with ethyl acetate, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, 30 g, ethyl acetate/hexane=2/98-+80/20) to give the title compound (157 mg, 58%) as a white powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445509B2
Source datasetuspto-grants-2013_05
ORD IDord-01b53812d77045e48253d0eda11e546b
Source noteuspto-grants-2013_05