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 1820630노트

반응식

HRID 1820630 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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 9, 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) δ 166.1, 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).

후처리

  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

출처 및 근거

ORD 기록
ord-2ac3a066d21c44cab7c0094e352806ad
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605161B2

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