1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamide

HRID 1177880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177880
CCN(C(C)C)C(C)C.[S:10]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)=[CH:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:52][CH2:53][C:54]([N:56]1[CH2:61][CH2:60][N:59]([C:62](=[O:73])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])[CH2:58][CH2:57]1)=[O:55]>CN(C=O)C.O>[O:55]=[C:54]([N:56]1[CH2:57][CH2:58][N:59]([C:62](=[O:73])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])[CH2:60][CH2:61]1)[CH2:53][NH:52][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][S:10][CH:11]=2)=[CH:23][CH:22]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7368624-(3-Thienyl)benzoic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Produkt 1

HCID 59559628N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamideAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (74.9 mg, 0.09 mL, 0.58 mmol) was added to a stirred solution of 4-thiophen-3-yl-benzoic acid (40 mg, 0.19 mmol) in DMF (1 mL). HOBT (32 mg, 0.23 mmol) and EDCI (45 mg, 0.23 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (100 mg, 0.23 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 46 mg (46.9% yield) of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamide. LCMS Purity: 97.5%. 1H NMR (DMSO-d6): δ 8.7-8.6 (m, 1H), 8.1-8.0 (s, 1H), 7.96-7.9 (m, 2H), 7.88-7.8 (m, 3H), 7.8-7.74 (m, 1H), 7.72-7.62 (m, 3H), 7.6-7.5 (bt, 1H), 4.24-4.08 (m, 2H), 3.78-3.56 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.06 (m, 2H).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0cbea3ab9cff4136b7c49272adcdad17
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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