1,2-Dichloroethane → HCID 57991969, Verbindung

HRID 2075334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075334
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:38][C:39]1[CH:44]=[N:43][CH:42]=[C:41]2[S:45][C:46]([C:48]3[S:52][C:51]([NH2:53])=[N:50][N:49]=3)=[CH:47][C:40]=12.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:38][C:39]1[CH:44]=[N:43][CH:42]=[C:41]2[S:45][C:46]([C:48]3[S:52][C:51]([NH:53][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=4)=[N:50][N:49]=3)=[CH:47][C:40]=12

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7020838N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninatoHCID 57991954HCID 57991954, Verbindung

Produkt 1

HCID 57991969HCID 57991969, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-2-((tert-Butoxycarbonyl)amino)-3-(3-(trifluoromethyl)phenyl)propanoic acid (1 g, 3 mmol) purchased from Peptech was mixed with EDC (0.766 g, 4 mmol) and HOBt (0.810 g, 6 mmol) in 5 mL DMF in a round bottom flask. The mixture was stirred at room temperature for 30 minutes. 5-(4-Chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-amine (0.268 g, 1 mmol) was added to the flask followed by addition of DIEA (1.4 mL, 8 mmol). The mixture was heated at 50° C. for one hour. After the DMF was removed under reduced pressure, the remaining residue was mixed with 200 mL EtOAc. The EtOAc solution was washed three times with saturated ammonium chloride aqueous solution, three times with saturated aqueous NaHCO3, and then dried over Na2SO4. After removing the solvent, the product was obtained and used directly in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated at 50° C. for one hour
  2. customAfter the DMF was removed under reduced pressure
  3. additionthe remaining residue was mixed with 200 mL EtOAc
  4. washThe EtOAc solution was washed three times with saturated ammonium chloride aqueous solution, three times with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customthe product was obtained

Quellen und Nachweise

ORD-Eintrag
ord-57f2b07691d343e09cb422de8eb1dbf0
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919504B2

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