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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 527299Generated: October 26, 2026

4-Dimethylamino-1-naphthaldehyde → 5-(((4-(dimethylamino)naphthalen-1-yl)methyl)amino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

https://huagongshe.com/reaction/527299

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Dimethylamino-1-naphthaldehydeHCID 608052—
Reactant5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamideHCID 86698959—
CatalystPiperidineHCID 8082—
SolventEthanolHCID 702—
Product5-(((4-(dimethylamino)naphthalen-1-yl)methyl)amino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamideHCID 178482794—

Reaction Steps

5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide 8 (100 mg) was suspended in EtOH (3 mL) and 4-Dimethylamino-1-naphthaldehyde (1 eq.) and piperidine (1 drop) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 5-(((4-(dimethylamino)naphthalen-1-yl)methyl)amino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09346792B2
Source datasetuspto-grants-2016_05
ORD IDord-ce9f4c882c2e4700829ba1a3c491a15e
Source noteuspto-grants-2016_05