Triethylamine → [4-(6-Chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone

HRID 499144노트

반응식

HRID 499144 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>ClCCl>[Cl:8][C:9]1[N:10]=[N:11][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:25]([C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[C:22]([F:21])([F:32])[F:33])=[O:26])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 52949263-Chloro-6-(1-piperazinyl)pyridazine

생성물 1

HCID 86024941[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (2.0 mL) was added to an ice cold solution of 3-chloro-6-piperazin-1-ylpyridazine (1.00 g, 6.69 mmol) in dichloromethane (10 mL), followed by the addition of 2-trifluoromethylbenzoyl chloride (2.10 g, 10.03 mmol). The mixture was allowed to warm up to room temperature and then stirred for 30 minutes. The solvent was removed in vacuo and the crude mixture was dissolved in ethyl acetate (15 mL), washed with water and dried over anhydrous Na2SO4. [4-(6-chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone was obtained as a thick liquid after purified by column chromatography in 79% yield (1.96 g). 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=7.9 Hz, 1H), 7.63-7.50 (m, 2H), 7.32 (d, J=7.3 Hz, 1H), 7.21 (t, J=4.4 Hz, 1H), 6.92 (d, J=9.5 Hz, 1H), 4.20-3.92 (m, 1H), 3.92-3.80 (m, 1H), 3.70-3.55 (m, 4H), 3.30 (t, J=5.3 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 167.6, 158.7, 147.7, 134.2, 134.2, 132.3, 129.5, 129.1, 127.2, 126.8, 126.8, 115.6, 46.3, 45.2, 44.7, 41.2. MS (ES+) m/z 371.1 and 373.1 (M+1).

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude mixture was dissolved in ethyl acetate (15 mL)
  3. washwashed with water
  4. dry with materialdried over anhydrous Na2SO4

출처 및 근거

ORD 기록
ord-55dea1ee0255481fa759d656bc5f1767
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767677B2

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