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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1915051Generated: November 2, 2026

Diisopropylethylamine → N-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamide

https://huagongshe.com/reaction/1915051

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant(3S)-pyrrolidin-3-olHCID 2733874—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acidHCID 51001626—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductN-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamideHCID 67042283—

Reaction Steps

A mixture of 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid (50 mg, 0.12 mmol), HATU (55 mg, 0.14 mmol) and N,N-diisopropylethylamine (34 mg, 0.26 mmol) in anhydrous DMF (8 ml) was stirred at room temperature for 10 minutes, followed by addition of (S)-3-pyrrolidinol (16 mg, 0.18 mmol). The mixture was stirred for another 10 minutes and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give N-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamide as white solid. Yield: 40 mg, 69%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08614234B2
Source datasetuspto-grants-2013_12
ORD IDord-cadfb9bdeb6c45a789a93a99b3f32832
Source noteuspto-grants-2013_12