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

HRID 499173ノート

反応式

HRID 499173 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08df919ae03c4aedae2faf745c877d2c
出典データセット
uspto-grants-2010_08
特許番号
US07767677B2

反応ノート

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