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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 589491Generated: October 30, 2026

Aniline → 4-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

https://huagongshe.com/reaction/589491

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnilineHCID 6115—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-(Dimethylamino)benzoyl chlorideHCID 4400782—
Reactant4-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamideHCID 86730983—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventPyridine methylene chlorideHCID 21875418—
Product4-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamideHCID 71230911—

Reaction Steps

To a solution of aniline Intermediate 6 (84 mg, 0.213 mmol) in DCM/pyridine (2:1, 30 ml) were added DIPEA (0.372 ml, 2.13 mmol), 4-dimethylaminobenzoyl chloride (43 mg, 0.234 mmol), and DMAP (2.6 mg, 0.021 mmol). The resulting mixture was stirred at room temperature for 75 hrs. The solvents were removed in vacuo and the resulting mixture was purified by reversed phase HPLC (MeCN/H2O) to afford Example 15.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09233111B2
Source datasetuspto-grants-2016_01
ORD IDord-aaee8eeac4e4474d826b1d814f3c5335
Source noteuspto-grants-2016_01