Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 90419167 | HCID 90419167 | — |
| Reactant | HCID 178491074 | HCID 178491074 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 90419149 | HCID 90419149 | 53% |
Reaction Steps
To a solution of compound 2 (100 mg, 0.20 mmol) in THF (20 mL) was added NaH (12 mg, 0.30 mmol) at 0° C. After stirred for 10 min, MeI (57 mg, 0.40 mmol) was added. The mixture was stirred for 2 h at room temperature and then diluted with H2O (20 mL) and EtOAc (50 mL). The organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by prep-TLC using PE/EtOAc=4/1 to give 4-((4-methoxybenzyl)((1-methyl-1H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (3) (55 mg, yield: 53%) as a yellow solid and 4-((4-methoxybenzyl)((2-methyl-2H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (4). ESI-MS: 461.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09353104B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-0a87bb8b48c444ef96eafdf402f6a338 |
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| Source note | uspto-grants-2016_05 |
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