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

HRID 499173Notes

Reaction equation

HRID 499173 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-08df919ae03c4aedae2faf745c877d2c
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

Loading…