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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1909035Generated: October 30, 2026

Lithium diisopropylamide → Benzonitrile, 4-[[5-[4-(diMethylaMino)-1-piperidinyl]-3H-iMidazo[4,5-b]pyridin-2-yl]carbonyl]-2-(1,3,5-triMethyl-1H-pyrazol-4-yl)-

https://huagongshe.com/reaction/1909035

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium diisopropylamideHCID 2724682—
Reactant[1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amineHCID 66599667—
Reactant3-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-terephthalamic acid methyl esterHCID 66599774—
ProductBenzonitrile, 4-[[5-[4-(diMethylaMino)-1-piperidinyl]-3H-iMidazo[4,5-b]pyridin-2-yl]carbonyl]-2-(1,3,5-triMethyl-1H-pyrazol-4-yl)-HCID 178434016—

Reaction Steps

Following General procedure P (LDA metallation, ketone formation and in situ deprotection) using 3-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-terephthalamic acid methyl ester and [1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amine to give 4-[5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzonitrile. (84%). HRMS m/z 501.2721 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598217B2
Source datasetuspto-grants-2013_12
ORD IDord-e10d8f992ded4ec29fb0c16de5deddc8
Source noteuspto-grants-2013_12