Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 66677471 | HCID 66677471 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 46941191 | HCID 46941191 | — |
Reaction Steps
To tert-butyl 2-((2-chloro-4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)(methyl)amino)acetate (0.192 g, 0.35 mmol) was added a 4N solution of HCl in dioxane (2 mL) and the reaction mixture stirred at 80° C. for 2 hours. The reaction mixture was allowed to cool and the solvent evaporated in vacuo. The residue was purified by SCX-2 chromatography eluting with methanol followed by DCM and ammoniacal MeOH (7M) to afford the title compound as a colorless gum. 1H NMR (CDCl3, 400 MHz) δ 8.38 (1H, s), 8.12 (1H, d, J=7.9 Hz), 8.07 (1H, d, J=8.0 Hz), 7.72 (1H, s), 7.55 (1H, d, J=8.1 Hz), 7.32-7.19 (4H, m), 7.10 (1H, d, J=7.4 Hz), 4.19 (4H, m), 3.57 (2H, s), 3.28 (3H, s), 2.72 (3H, s), 2.05 (3H, s). LC/MS (Method A): 492 (M+H)+. HPLC (Method F) Rt 3.19 min (Purity: 98.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815919B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-b79b9672a97e42bfac713b901e44024a |
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| Source note | uspto-grants-2014_08 |
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