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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 476006Generated: October 30, 2026

Sodium Carbonate → HCID 178425144, compound

https://huagongshe.com/reaction/476006

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
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—
ReactantHCID 178514825HCID 178514825—
CatalystHCID 178418476HCID 178418476—
SolventDimethyl SulfoxideHCID 679—
ProductHCID 178425144HCID 178425144—

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 (70 mg, 0.187 mmol), 1H-1,2,3-benzotriazol-5-ylboronic acid (39.7 mg, 0.243 mmol), DMSO (2 mL), sodium carbonate (0.281 mL, 0.562 mmol) and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 22 mg (26%). LCMS E-S (M+H)=457.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (d, 6 J=6.4 Hz, H), 2.14 (s, 3H), 2.24 (s, 3H), 4.43 (d, J=4.3 Hz, 2H), 5.31-5.46 (m, 1H), 5.91 (s, 1H), 8.07 (br. s., 1H), 8.34 (s, 1H), 8.41 (m, 2H), 8.85 (br. s., 1H), 9.02 (br. s., 1H), 11.59 (br. s., 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08637509B2
Source datasetuspto-grants-2014_01
ORD IDord-aeb6d1246f724137bccff1bb951aedd7
Source noteuspto-grants-2014_01