Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | 1-Cyclohexylpiperazine | HCID 87298 | — |
| Reactant | HCID 90410908 | HCID 90410908 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 3666186 | HCID 3666186 | 91% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08999992B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-90ddf2c800a949ada8b3c97cc1ff27f5 |
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| Source note | uspto-grants-2015_04 |
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