Potassium Carbonate → 5-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

HRID 1689847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689847
[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13](Cl)=[C:14]([Br:16])[CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:33]([F:36])([F:35])[F:34])=[C:23]([C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:30]3[CH2:31][CH2:32][N:27]([C:25](=[O:26])[C:23]4[CH:24]=[C:19]([F:18])[CH:20]=[CH:21][C:22]=4[C:33]([F:36])([F:35])[F:34])[CH2:28][CH2:29]3)=[C:14]([Br:16])[CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 57875818(5-Fluoro-2-trifluoromethylphenyl)piperazin-1-ylmethanoneHCID 86028518HCID 86028518, Verbindung

Produkt 1

HCID 112961565-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-6-chloro-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.432 g, 1.272 mmol) in dioxane (15.0 mL) was added (5-fluoro-2-trifluoromethylphenyl)piperazin-1-yl-methanone (0.386 g, 1.399 mmol), potassium carbonate (0.703 g, 5.080 mmol) and tetrabutyl ammonium bromide (0.042 g, 0.130 mmol). The resulting mixture was stirred at reflux for 48 h, filtered and then concentrated in vacuo. The crude product was purified by column chromatography, eluting with a solvent gradient of 35% ethyl acetate and 65% hexane to yield the desired product (0.235 g, 32%). 1H NMR (300 MHz, CDCl3) δ 8.59-8.58, 8.16-8.15, 7.74-7.69, 7.24-7.18, 7.08-7.04, 4.97-4.93, 4.03-3.85, 3.60-3.55, 3.43-3.33, 3.07-2.99, 1.41-1.34, 0.60-0.53, 0.43-0.37, 0.025-0.015. 13C NMR (75 MHz, CDCl3) δ166.1, 162.6, 145.4, 141.1, 130.5, 129.6, 129.5, 116.7, 116.4, 114.9, 114.7, 110.3, 48.8, 48.6, 46.9, 43.5, 41.6, 34.5, 8.2, 4.2. MS (ES+) m/z 581 (M+1).

Aufarbeitung

  1. temperatureat reflux for 48 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography
  5. washeluting with a solvent gradient of 35% ethyl acetate and 65% hexane

Quellen und Nachweise

ORD-Eintrag
ord-1a0d8625564647d2b71c3308b983c7dc
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153636B2

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