Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | HCID 67351988 | HCID 67351988 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67351816 | HCID 67351816 | 41% |
Reaction Steps
Compound 18 (169 mg, 0.427 mmol) obtained in Example 18 was dissolved in ethanol (2.1 mL), and the mixture was stirred overnight at 80° C. after adding hydrazine.monohydrate (0.207 mL, 4.27 mmol). The reaction mixture was then concentrated under reduced pressure, and vacuum dried. The resulting residue was dissolved in DMF (2 mL), and stirred overnight after adding acetyl chloride (0.0455 mL, 0640 mmol) and triethylamine (0.119 mL, 0.854 mmol). Then, the reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give the title compound (Compound 19) (74.0 mg, 41% (2 steps)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07998954B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-ec9a278cacfc4f02ad4ebdfcdc4c9c1b |
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| Source note | uspto-grants-2011_08 |
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