Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | HCID 21054585 | HCID 21054585 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 21054582 | HCID 21054582 | 58% |
Reaction Steps
To a solution of (9S)-9-acetoxy-1-butyl-9-ethyl-1H,12H-pyrano[3″,4″:6′,7′]indolizino-[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-2,10,13(3H,9H,15H)-trione (11.5 mg, 0.023 mmol) in MeOH (3 ml) cooled in an ice-bath was added anhydrous hydrazine (100 μl). The mixture was warmed to room temperature and stirred for 1 hr. Aqueous 1 N HCl solution was added dropwise to acidify the reaction mixture and the mixture was stirred for 1 hr. at room temperature. After concentrated under reduced pressure, the obtaining residue was extracted with CH2Cl2 (20 ml×3). The combined CH2Cl2 solution was washed with brine, dried over MgSO4 and evaporated. The residue was purified by column chromatography (dichloromethane/methanol=30/1) to give pure product (6.1 mg, 58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06825194B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-cfe24ca18f5940e49b3cd38787fdd187 |
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| Source note | uspto-grants-2004_11 |
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