Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 118021461 | HCID 118021461 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 118022352 | HCID 118022352 | 74% |
Reaction Steps
The title compound of Example 90, step 2 (30 mg, 0.075 mmol) in N,N-dimethylacetamide was treated with excess 25% sodium methoxide in methanol and heated at 85° C. until complete. Silica gel chromatography (40-80% EA in hexane over 8 min, then isocratic) gave the title compound 23 mg, 0.056 mmol, 74%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.06-0.20 (m, 2H) 0.27-0.43 (m, 2H) 0.83-1.05 (m, 1H) 3.22 (s, 3H) 3.53 (s, 3H) 3.73 (s, 3H) 3.83-4.16 (m, 2H) 6.47 (s, 1H) 7.04-7.20 (m, 1H) 7.36 (d, J=8.59 Hz, 1H) 7.50 (s, 1H) 7.81 (s, 1H) 7.96 (d, J=6.82 Hz, 1H) 8.23 (d, J=8.59 Hz, 1H). LCMS: 414 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09034900B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-4be6389ec1ff42dab0086c7beced5768 |
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| Source note | uspto-grants-2015_05 |
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