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

HRID 32728

反応式

HRID 32728 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-a4c32b96617f474fb32d70c7f6e317c6
出典データセット
uspto-grants-2008_09
特許番号
US07427612B2

関連ノート

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