Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 1,2-Dichloroethane | HCID 11 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | 4-Isopropoxy-3-(trifluoromethyl)benzoic acid | HCID 22597767 | — |
| Edukt | HCID 178471833 | HCID 178471833 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 59318349 | HCID 59318349 | 31,7% |
Reaktionsschritte
4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)benzoic acid (D71) (136 mg, 0.55 mmol), EDC (116 mg, 0.61 mmol) and HOBt (82 mg, 0.61 mmol) were stirred in N,N-dimethylformamide (5 mL) for 20 min. Ethyl 3-{-4-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D57) (150 mg, 0.55 mmol) was added and the reaction stirred at room temperature for 3 h and then 80° C. for 18 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was washed with aqueous sodium bicarbonate (25 mL) and water (25 mL) before it was dried (phase separator), filtered and concentrated in vacuo. The residue was triturated with ethanol to give the title compound (85 mg). δH (d6-DMSO, 400 MHz): 8.44 (1H, dd), 8.35 (1H, d), 7.95 (1H, d), 7.81 (1H, d), 7.62-7.58 (2H, m), 7.36 (1H,app. t), 7.07 (1H, d), 4.99 (1H, septet), 4.54 (2H, t), 4.02 (2H, q), 2.89 (2H, t), 1.36 (6H, d), 1.11 (3H, t). MS (ES+): C26H24F3N3O4 requires 487; found 488 (MH+).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08101775B2 |
|---|
| Quelldatensatz | uspto-grants-2012_01 |
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| ORD ID | ord-62b7b3651d5742e4a3ea7bc0a39afcaf |
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| Quellennotiz | uspto-grants-2012_01 |
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