Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl N-[(4-aminophenyl)methyl]carbamate | HCID 2756041 | — |
| Reactant | 5-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one | HCID 10732015 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 69154117 | HCID 69154117 | 55.5% |
Reaction Steps
To a stirred solution of 100 mg (0.348 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (6 ml), (4-aminobenzyl)carbamic acid tert-butyl ester (Gallo-Rodriguez, C et al J. Med. Chem. 1994, 37(5), 636-46) (1.16 mg, 0.52 mmol) was added portionwise. The resulting mixture was stirred at room temperature for 1 h. The precipitate thus formed was collected by filtration and washed with diethylether. Then it was solved in dichloromethane (1 mL) and trifluoroacetic acid (0.23 mL, 3.03 mmol) was added dropwise. The final mixture was stirred at room temperature for 20 minutes. Some more dichloromethane was added and this solution was washed with saturated K2CO3 solution until pH 6. The organic layer was dried and solvent removed to yield 70 mg (54% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07459453B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-a80314914e0d4925acf959483cc588ba |
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| Source note | uspto-grants-2008_12 |
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