Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(4-Chlorobutyl)pyridine--hydrogen chloride (1/1) | HCID 19766757 | — |
| Reactant | HCID 68429305 | HCID 68429305 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68432148 | HCID 68432148 | 12.2% |
Reaction Steps
4-Bromo-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one (221 mg, 0.677 mmol) in N,N-dimethylformamide (4 mL) was mixed with 4-(4-chlorobutyl)pyridine hydrochloride (278 mg, 1.35 mmol) and potassium carbonate (375 mg, 2.71 mmol) at room temperature and stirred at 80° C. for 6.5 hours. After cooling, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=50/1) to give the desired product (38 mg, 12% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440666B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-2418d7a6214f4244a4e3953fb7f1ee0b |
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| Source note | uspto-grants-2013_05 |
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