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

HRID 1689847ノート

反応式

HRID 1689847 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 57875818(5-Fluoro-2-trifluoromethylphenyl)piperazin-1-ylmethanoneHCID 86028518HCID 86028518、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1a0d8625564647d2b71c3308b983c7dc
出典データセット
uspto-grants-2012_04
特許番号
US08153636B2

反応ノート

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