2-(Trifluoromethyl)benzoyl chloride → Piperazine,1-[5-(1h-benzo[d]imidazol-2-yl)-2-pyridinyl]-4-[2-(trifluoromethyl)benzoyl]-

HRID 499173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499173
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1COCC1.ClCCl.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35]>C(N(CC)CC)C>[NH:17]1[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=[C:13]1[C:10]1[CH:9]=[CH:8][C:7]([N:1]2[CH2:6][CH2:5][N:4]([C:34]([C:33]3[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=3[C:31]([F:30])([F:41])[F:42])=[O:35])[CH2:3][CH2:2]2)=[N:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 21919333Tetrahydrofurane dichloromethaneHCID 675232322-(6-Piperazin-1-YL-pyridin-3-YL)-1H-benzoimidazole

Produkt 1

HCID 11712097Piperazine,1-[5-(1h-benzo[d]imidazol-2-yl)-2-pyridinyl]-4-[2-(trifluoromethyl)benzoyl]-Ausbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To the suspension of 2-(6-piperazin-1-ylpyridin-3-yl)-1H-benzoimidazole (0.403 g, 1.440 mmol) in 25 mL of mixture of THF:dichloromethane (1:1) was added 2-trifluoromethylbenzoyl chloride (0.300 g, 1.440 mmol) in the presence of triethylamine (1 mL). The mixture was stirred at room temperature for 1 hour. The solvent was then evaporated and ethyl acetate was added. The suspension was ultrasonicated and filtered. The filtrate was concentrated in vacuo and the residue was subjected to column chromatography. The title compound was obtained as a white solid in 15% yield (0.097 g). 1H NMR (300 MHz, CDCl3) δ 8.71 (s, 1H), 8.24 (dd, J=2.4 and 9.0 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.74 (t, J=7.5 Hz, 1H), 7.63 (t, J=7.5 Hz, 1H), 7.52-7.48 (m, 2H), 7.51 (d, J=7.5 Hz, 1H), 7.14-7.11 (m, 2H), 6.97 (d, J=9.0 Hz, 1H), 3.78-3.71 (m, 4H), 3.60-3.46 (m, 2H), 3.29-3.11 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 166.8, 159.2, 150.4, 146.8, 136.1, 135.1, 135.1, 133.4, 130.1, 128.0, 127.1, 127.0, 126.1, 126.0, 125.6, 122.4, 116.2, 107.4, 46.6, 44.6, 44.4, 41.4. MS (ES+) m/z 452.3 (M+1).

Aufarbeitung

  1. customThe solvent was then evaporated
  2. additionethyl acetate was added
  3. customThe suspension was ultrasonicated
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08df919ae03c4aedae2faf745c877d2c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767677B2

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