Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Edukt | 3-Cyano-4-fluorobenzoic acid | HCID 2773932 | — |
| Edukt | HCID 178509599 | HCID 178509599 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 178511967 | HCID 178511967 | 72% |
Reaktionsschritte
Part B: 3-Cyano-N—{(S)-1-[4-(4-cyano-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-4-fluoro-benzamide: A mixture of the compound of Example 176 Part A (100 mg, 0.28 mmol), 3-cyano-4-fluorobenzoic acid (46 mg, 0.28 mmol), triethylamine (0.085 mL, 0.61 mmol) and BOP (0.18 g, 0.4 mmol) in THF (5 mL) was stirred at rt overnight under N2. Reaction mixture was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with sat'd. NaHCO3 and brine and then dried over anhydrous Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/EtOAc) provided the amide product (88 mg, 72%). 1H NMR (500 MHz, CDCl3) δ 3.41 (dd, J=13.75, 7.15 Hz, 1H) 3.58 (dd, J=13.47, 7.97 Hz, 1H) 5.33 (q, J=7.70 Hz, 1H) 7.01-7.09 (m, 1H) 7.18-7.37 (m, 7H) 7.66 (d, J=8.25 Hz, 2H) 7.85 (d, J=8.25 Hz, 2H) 7.89-7.96 (m, 1H) 7.95-8.03 (m, 1H) 9.74 (s, 1H). m/z 436.1 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08716492B2 |
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| Quelldatensatz | uspto-grants-2014_05 |
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| ORD ID | ord-ba0fb6468f544d59b8f3705cd3c4a8fa |
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| Quellennotiz | uspto-grants-2014_05 |
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