Dimethylformamide → [3-(4-{1-[4-(4-Chloro-phenoxy)-phenyl]-2-phenethyl-1h-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

HRID 901691ノート

反応式

HRID 901691 の反応式
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:2]=1.C[N:17]([CH:19]=O)C.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=1)=O>O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[CH:2]=[CH:1][C:6]([N:7]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=4)[N:17]=[C:19]3[CH2:22][CH2:23][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:5][CH:4]=2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 75784-(4-Chlorophenoxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

生成物 1

HCID 59698958[3-(4-{1-[4-(4-Chloro-phenoxy)-phenyl]-2-phenethyl-1h-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 4-amino-4′-chlorodiphenyl ether (1.2 eq., 6.2 mmol) in anhydrous DMF (10 mL) DIEA (3 eq. 16 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (5.2 mmol), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC or HPLC. The reaction mixture was then diluted with cold H2O and the product was extracted in EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product obtained from 2–4% MeOH/DCM (yield ˜22%).

後処理

  1. extractionthe product was extracted in EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of solvent in vacuuo

出典と根拠

ORDレコード
ord-9224dfcf93cc4375b1e84b0d23d25eaf
出典データセット
uspto-grants-2008_04
特許番号
US07361678B2

反応ノート

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