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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 476012Generated: October 29, 2026

4-Aminopyridine → HCID 56598681, compound

https://huagongshe.com/reaction/476012

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-AminopyridineHCID 1727—
ReactantCesium carbonateHCID 10796—
ReactantBinap, (A+-)-HCID 634876—
Reactant6-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamideHCID 56597425—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 56598681HCID 56598681—

Reaction Steps

The title compound was prepared in the same manner as described in example 74 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (50 mg, 0.134 mmol), 4-pyridinamine (12.59 mg, 0.134 mmol), cesium carbonate (131 mg, 0.401 mmol), 1,4-dioxane (2 mL), palladium(II) acetate (1.501 mg, 6.69 μmol) and BINAP (8.33 mg, 0.013 mmol), wherein the reaction time was 2 h. The final product was collected as 29 mg (50%). LCMS E-S (M+H)=432.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45-1.59 (d, J=6.8 Hz, 6H), 2.14 (s, 3H), 2.23 (s, 3H), 4.36 (d, J=5.0 Hz, 2H), 5.16 (m, 1H), 5.91 (s, 1H), 7.09 (s, 1H), 7.99 (d, J=6.1 Hz, 2H), 8.12 (s, 1H) 8.49 (d, J=6.6 Hz, 2H), 8.74 (t, J=5.1 Hz, 1H), 10.58 (s, 1H), 11.58 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08637509B2
Source datasetuspto-grants-2014_01
ORD IDord-52ad821a648247a7bee29e40e9e53195
Source noteuspto-grants-2014_01