Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | HCID 67451381 | HCID 67451381 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 68224035 | HCID 68224035 | 75% |
Reaction Steps
To a solution of 112 (560 mg, 0.923 mmol) in DCM (10 mL) was added 4.0M HCl in dioxane (0.923 mL, 3.69 mmol) and the reaction mixture was stirred at RT for 2 hours. The mixture was diluted with saturated NaHCO3 solution and the layers were separated. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with Et2O to afford title compound 113 (350 mg, 75% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.48 (d, J=5.48 Hz, 1H), 8.00 (s, 1H), 7.82 (d, J=8.41 Hz, 1H), 7.70 (m, 1H), 7.44 (d, J=8.22 Hz, 1H), 7.36 (t, J=9.19 Hz, 1H), 7.19 (m, 1H), 6.56 (m, 2H), 3.75 (s, 2H), 3.39 (t, J=5.67 Hz, 2H), 3.22 (s, 3H), 2.64 (t, J=5.67 Hz, 2H), 2.53 (m, 1H), 0.63 (m, 2H), 0.41 (m, 2H). MS (m/z)=507.5 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906852B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-7097cc4c061246e792c5345f51c46ec6 |
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| Source note | uspto-grants-2014_12 |
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