1,2-Dichloroethane → HCID 59318349, Verbindung

HRID 423347

Reaktionsgleichung

Reaktionsgleichung von HRID 423347
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O[NH:33][C:34](=[NH:51])[C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH:37]=[CH:38][N:39]2[CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>CN(C)C=O>[CH3:3][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:51]=[C:34]([C:35]3[CH:43]=[CH:42][CH:41]=[C:40]4[C:36]=3[CH:37]=[CH:38][N:39]4[CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[N:33]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:1]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidHCID 178471833HCID 178471833, Verbindung

Produkt 1

HCID 59318349HCID 59318349, VerbindungAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  1. wait80° C. for 18 h
  2. customThe reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
  3. washThe organic layer was washed with aqueous sodium bicarbonate (25 mL) and water (25 mL) before it
  4. customwas dried (phase separator)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-62b7b3651d5742e4a3ea7bc0a39afcaf
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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