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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 930191Generated: October 30, 2026

Hydrochloric Acid → HCID 89717670, compound

https://huagongshe.com/reaction/930191

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant1,4-DioxaneHCID 31275—
ReactantTributyltin azideHCID 4984872—
ReactantHCID 89719245HCID 89719245—
SolventDiethyl EtherHCID 3283—
Solvent(Trifluoromethyl)benzeneHCID 7368—
ProductHCID 89717670HCID 89717670104.5%

Reaction Conditions

Temperature180 °C

Reaction Steps

In a 2-5 mL microwave vial was added 4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carbonitrile (47.5 mg, 0.142 mmol) and azidotributyltin (409 μl, 1.491 mmol) in (trifluoromethyl)benzene (2 mL) to give a tan suspension. The vial was placed in the microwave and heated to 180° C. for 30 minutes. The mixture was concentrated to dryness and MeOH (3 mL) followed by HCl 4M in Dioxane (1.07 mL, 4.26 mmol) was added to get a yellow solution. To the resulting solution was added diethyl ether (3 mL) Stirred at 20° C. for 16 hours. The solid obtained was collected on a Buchner. The cake was washed with diethyl ether (3×1 mL) and with Hexane (3×1 mL) and the solid dried at 30° C. under high vacuum until constant weight to afford 56 mg of the title compound as the HCl salt. LCMS m/z 378.2 (M+H)+, retention time (on analytical HPLC)=1.30 minutes.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09296744B2
Source datasetuspto-grants-2016_03
ORD IDord-709bb6f05546411abb3138be4e120721
Source noteuspto-grants-2016_03