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

HRID 1820629노트

반응식

HRID 1820629 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 5-bromo-6-chloro-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.432 9,1.272 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) δ 166.1, 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).

후처리

  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

출처 및 근거

ORD 기록
ord-a3ab60c4dc304525a481995b28e500cc
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605161B2

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