Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1465679Generated: October 30, 2026

Methanol → HCID 3666186, compound

https://huagongshe.com/reaction/1465679

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
Reactanttert-Butyl methyl etherHCID 15413—
Reactant1-CyclohexylpiperazineHCID 87298—
ReactantHCID 90410908HCID 90410908—
SolventDimethyl SulfoxideHCID 679—
ProductHCID 3666186HCID 366618691%

Reaction Conditions

Temperature65 °C

Reaction Steps

About 70 g of 4-((3-bromo-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid was dissolved in 950 mL of DMSO. About 50 mL of TEA and 50 g of 1-cyclohexyl piperazine were added to the reaction. Temperature was raised to 60-70° C. After 2-3 hours, slowly added 500 mL of MTBE and MeOH (10:1) solution and adjusted the temperature to 40-50° C. The solid was centrifuged and washed by 100 mL of MTBE and MeOH solution and followed by 100 mL of MeOH. Solid was dried under reduced pressure at 25-30° C. for 12-24 hours to obtain the 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid at about 98% purity and about 91% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08999992B2
Source datasetuspto-grants-2015_04
ORD IDord-90ddf2c800a949ada8b3c97cc1ff27f5
Source noteuspto-grants-2015_04