Participants
| Role | Name | HCID | Charge |
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| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 59376879 | HCID 59376879 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58298740 | HCID 58298740 | 37.5% |
Reaction Steps
The product from Example 7C (40 mg, 0.050 mmol) was dissolved in dioxane (2.0 mL) and 4M HCl in dioxane (0.25 mL) was added. This solution was stirred at room temperature overnight. The solid HCl salt of the product was filtered off then dissolved in methanol and added to saturated NaHCO3. Extracted with ethyl acetate and evaporated. Purification by chromatography on silica gel eluting with (0% to 30% methanol in dichloromethane) gave the title compound (13 mg, 37% yield). 1H NMR (300 MHz, DMSO-D6) d ppm 1.36 (dd, J=6.80, 4.23 Hz, 12H) 3.20-3.30 (m, 2H) 6.57 (d, J=8.46 Hz, 2H) 7.04-7.12 (m, 3H) 7.60-7.70 (m, 2H) 7.82-7.95 (m, 3H) 8.00-8.08 (m, 2H) 8.29 (s, 1H) 8.83-8.93 (m, 2H) 9.09 (d, J=12.50 Hz, 1H) 9.17 (d, J=7.72 Hz, 1H) 10.58 (s, 1H) 11.38 (s, 1H) 11.69 (s, 1H). MS (ESI) m/z 693 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09249138B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-4f1f4ff222b046e7a0769753ffa04d40 |
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| Source note | uspto-grants-2016_02 |
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