Imidazole → 1-{3-Fluoro-4-[4-(5-imidazol-1-yl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone

HRID 736198

반응식

HRID 736198 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:11][CH2:10]1)=[O:8].[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.O1CCOCC1>[F:24][C:16]1[CH:17]=[C:18]([C:21](=[O:23])[CH3:22])[CH:19]=[CH:20][C:15]=1[N:12]1[CH2:13][CH2:14][N:9]([C:7](=[O:8])[C:6]2[CH:25]=[C:2]([N:32]3[CH:36]=[CH:35][N:34]=[CH:33]3)[CH:3]=[CH:4][C:5]=2[N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH2:10][CH2:11]1

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 445805131-(4-(4-(5-Bromo-2-morpholinobenzoyl)piperazin-1-yl)-3-fluorophenyl)ethanone

생성물 1

HCID 597936961-{3-Fluoro-4-[4-(5-imidazol-1-yl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone수율 41.9%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

In a tube were added successively 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (example BJ, 0.05 g, 0.1 mmol), imidazole (8.4 mg, 0.12 mmol), cesium carbonate (70 mg, 0.21 mmol), CuI (4 mg, 0.02 mmol), 1,10-phenanthroline (7.3 mg, 0.04 mmol) and dioxane (0.2 ml). The mixture was heated under argon at 120° C. for 12 hours. The reaction mixture was cooled to room temperature and quenched with water/ethyl acetate. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: CH2Cl2/methanol: 0-5% to provide the title compound as a brown solid (20 mg, 40%), MS (m/e): 478.4 (M+H, 100%)

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water/ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethylacetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was chromatographed over silicagel

출처 및 근거

ORD 기록
ord-dd234e85be364f4fbb1e39828c5815e6
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595314B2

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