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

HRID 1689848ノート

反応式

HRID 1689848 の反応式
[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:33])[F:32])[CH2:19][CH2:18]3)=[C:14](Br)[CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:32])[F:33])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

参加物

4

反応物 1

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

生成物 1

HCID 113640636-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridine-3-sulfonic acid (2-cyclopropylethyl)amide収率 24%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a stirred solution of 5-bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.100 g, 0.173 mmol) in methanol (5.0 mL) was added Pd/C (0.050 g, 12 mol %). The mixture was placed under an atmosphere of hydrogen for 24 hours. The reaction mixture was filtered through celite and 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 (0.020 g, 24%). 1H NMR (300 MHz, CDCl3) δ 8.58-8.57, 7.87-7.83, 7.76-7.71, 7.26-7.23, 7.08-7.04, 6.65-6.62, 4.60-4.56, 4.00-3.93, 3.86-3.64, 3.32-3.28, 3.04-2.97, 1.40-1.33, 0.59-0.53, 0.43-0.37, 0.025-0.008. 13C NMR (75 MHz, CDCl3) δ166.1, 162.6, 159.7, 148.2, 136.7, 129.7, 125.1, 124.7, 116.8, 116.5, 114.9, 114.7, 105.8, 46.5, 44.3, 44.2, 43.4, 41.4, 34.4, 8.2, 4.2. MS (ES+) m/z 501 (M+1).

後処理

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with a solvent gradient of 35% ethyl acetate and 65% hexane

出典と根拠

ORDレコード
ord-d81bba51e86243bba4bd92a5461fda01
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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