Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 87192444 | HCID 87192444 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 87191929 | HCID 87191929 | 71.5% |
Reaction Steps
A solution of Example 178a (90.0 mg, 0.181 mmol) in dioxane (2.5 mL) was treated with 20% NaOH (0.12 mL). The reaction was heated at 50° C. for 4 hours. The solvent was evaporated and the residue was triturated with water. The solid was filtered and purified by reverse-phase HPLC as described in Example 56 to give the title compound (46.2 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 1.23-1.39 (m, 3H), 1.40-1.55 (m, 2H), 1.69 (m, 1H), 1.76-1.88 (m, 2H), 2.00-2.12 (m, 2H), 3.75 (m, 1H), 3.96 (s, 3H), 6.90 (d, J=1.22 Hz, 1H), 7.00 (d, J=1.53 Hz, 1H), 7.91 (d, J=2.44 Hz, 1H), 7.99 (s, 1H), 8.09 (d, J=2.75 Hz, 1H). MS (ESI+) m/z 357.5 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08435980B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-c33cd611cbf44e9e94d55e3c23c09572 |
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| Source note | uspto-grants-2013_05 |
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