Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 22934024 | HCID 22934024 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18447172 | HCID 18447172 | 76.8% |
Reaction Steps
Triethylamine (0.14 ml, 1.0 mmol) was added to a mixture of the 4-methyl-5-(piperidin-3-yloxy)-1H-indazole (92 mg, 0.40 mmol) obtained in Example 422, acetic acid (24 mg, 0.40 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (77 mg, 0.40 mmol), 1-hydroxybenzo-triazole (54 mg, 0.40 mmol) and N,N-dimethylformamide (1.5 ml), and the resulting mixture was stirred at room temperature for 19 hours. The mixture was diluted with a mixed solution of ethyl acetate (10 ml)/toluene (10 ml) and washed with water and then a saturated aqueous sodium hydrogencarbonate solution. The mixture washed was dried over potassium carbonate and then concentrated to dryness to obtain 5-[(1-acetylpiperidin-3-yl)oxy]-4-methyl-1H-indazole (84 mg, 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07199147B2 |
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| Source dataset | uspto-grants-2007_04 |
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| ORD ID | ord-44704d39dc5c4ba9981d5dadce7b8eb1 |
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| Source note | uspto-grants-2007_04 |
|---|