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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 74633Generated: October 25, 2026

Diisopropylethylamine → 1-{1-[6-(5-Chloro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

https://huagongshe.com/reaction/74633

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantBms-973013HCID 22293182—
Reactant(5-Chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanoneHCID 58117515—
SolventDimethylformamideHCID 6228—
Product1-{1-[6-(5-Chloro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-oneHCID 58386622—

Reaction Steps

80 mg (0.27 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (dihydrochloride) were added to 100 mg (0.34 mmol) (5-chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone and 100 μL (0.58 mmol) DIPEA in 10 mL DMF. The reaction mixture was stirred for 22 h at RT and then evaporated down i. vac. The residue was combined with 20 mL water and stirred for 30 min at RT. The precipitated product was suction filtered. The purification was carried out using a silica gel column. The product fractions were combined and the solvent was eliminated using the rotary evaporator. The residue was stirred with water, suction filtered and dried.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829006B2
Source datasetuspto-grants-2014_09
ORD IDord-3b2d427af17f47889012c9eb56d19d5e
Source noteuspto-grants-2014_09