HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Exatecan intermediate 9
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide | HCID 10220585 | — |
| Reactant | (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione | HCID 10220900 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Exatecan intermediate 9 | HCID 12067229 | 59.1% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
To 150 mg of 2-acetylamino-8-amino-6-fluoro-5-methyl-1-tetralone and 158 mg of (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 30 ml of toluene and then 150 mg of pyridinium p-toluenesulfonate were added, followed by heating at an external temperature of 120° C. under reflux for 28 hours. After completion of the reaction, the solvent was removed under reduced pressure. Acetone was added to the residue and crystals so precipitated were collected by filtration, whereby 169 mg of the title compound were obtained. Melting point: 225-235° C. (decomposed)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06552197B2 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-0d155233dab94487a539ee2f46cdfa33 |
| Source note | uspto-grants-2003_04 |