Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydrazinecarboxaldehyde | HCID 12229 | — |
| Reactant | HCID 67051496 | HCID 67051496 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178527313 | HCID 178527313 | 76% |
Reaction Steps
A mixture of 39 (300 mg, 0.70 mmol), formic hydrazide (209 mg, 3.47 mmol) and Et3N (759 μM, 6.95 mmol) in EtOH (10.4 mL) was heated at 75° C. overnight. After cooling, the solvent was evaporated and the residue purified by silicagel chromatography using 80% ethyl acetate in hexane (gradient elution) then preparative TLC (1 mm plates, EtOAc eluent) to give 40 as a white solid (132.6 mg, 76%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 6.71 (m, 1H), 7.40-7.70 (m, 5H), 7.84 (s, 1H), 7.93 (t, J=1.0 Hz, 1H), 8.10-8.30 (m, 3H), 8.63 (d, J=2.0 Hz, 1H), 9.10 (bs, NH); MS (CI) m/z 391.9 (MH+), 433.1 (M+MeCN).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07432375B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-dd4773b99aa9437599a0369e1ae53b4b |
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| Source note | uspto-grants-2008_10 |
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