Diisopropylethylamine → 2-[4-(3-Chloropyridin-2-yl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

HRID 730707

Reaktionsgleichung

Reaktionsgleichung von HRID 730707
Cl.[Cl:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.Cl[C:16]1[NH:20][C:19]2[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:18]=2[N:17]=1.C(N(CC)C(C)C)(C)C>CC#N>[Cl:2][C:3]1[C:4]([N:9]2[CH2:10][CH2:11][N:12]([C:16]3[NH:20][C:19]4[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:18]=4[N:17]=3)[CH2:13][CH2:14]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazoleHCID 204550741-(3-Chloropyridin-2-yl)piperazine hydrochloride

Produkt 1

HCID 117106792-[4-(3-Chloropyridin-2-yl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of the hydrochloride salt from step (b) above (0.564 g, 2.4 mmol), 2-chloro-6-trifluoromethyl-1H-benzoimidazole (0.27 g, 1.22 mmol, Example 1c) and N,N-diisopropylethylamine (0.84 mL, 4.8 mmol, Aldrich) in MeCN (1 mL) was subjected to microwave irradiation at 180° C. with stirring for 20 min. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexane, to give the title compound as a white solid. M.p. 208-210° C. MS (ESI, pos. ion) m/z: 382 (M+1).

Aufarbeitung

  1. customirradiation at 180° C.
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 30% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e5544c1df3904204b9b36f20069d17c1
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582761B2

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