Water → 2-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

HRID 912760

Reaktionsgleichung

Reaktionsgleichung von HRID 912760
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.O>CS(C)=O>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[C:17]=1[N:23]1[CH2:28][CH2:27][N:26]([C:2]2[NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazoleHCID 114923451-(2,6-Dichlorophenyl)piperazine

Produkt 1

HCID 100474472-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of the benzoimidazole from step (c) above (75 mg, 0.34 mmol), the piperazine from step (a) above (90 mg, 0.39 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in DMSO (2 mL) was stirred at 80° C. for 24 h. The mixture was cooled to room temperature, water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (2×10 mL) and brine (5 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexane to give the title compound as a white solid. M.p. 263-265° C. MS (ESI, pos. ion) m/z: 415 (M+1).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic phases were washed with water (2×10 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d733d12a73de412484663657742d8122
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026241B2

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