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

HRID 499173노트

반응식

HRID 499173 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08df919ae03c4aedae2faf745c877d2c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767677B2

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