Dimethyl Sulfoxide → 2-Piperazin-1-yl-6-trifluoromethyl-1H-benzoimidazole

HRID 730703

Reaktionsgleichung

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.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CS(C)=O>O>[N:15]1([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)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-chloro-6-trifluoromethyl-1H-benzoimidazole (221 mg, 1 mmol, Example 1c), piperazine (172 mg, 2 mmol, Aldrich) and 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 (2×5 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 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 271 (M+1).

Aufarbeitung

temperatureThe mixture was cooled to room temperature
extractionthe mixture was extracted with EtOAc (2×20 mL)
washThe combined organic phases were washed with water (2×5 mL) and brine (5 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

Quellen und Nachweise

ORD-Eintrag: ord-e86feb2cc7564c5fb9120f920da27bee
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07582761B2

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