Dimethylformamide → [3-(4-{2-butyl-1-[4-(4-chloro-2-cyclohexyl-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

HRID 17728

반응식

HRID 17728 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[C:4]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1.C[N:23]([CH:25]=O)C.Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:33][CH:32]=1)=O>O.CCOC(C)=O>[CH2:15]([C:25]1[N:11]([C:10]2[CH:12]=[CH:13][C:7]([O:6][C:5]3[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][C:4]=3[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:8][CH:9]=2)[CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:33][CH:32]=2)[N:23]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 686845334-(4-Chloro-2-cyclohexylphenoxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

생성물 1

HCID 59699407[3-(4-{2-butyl-1-[4-(4-chloro-2-cyclohexyl-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-(4-chloro-2-cyclohexylphenoxy)aniline (1.2 eq., 2.5 mmol) in anhydrous DMF (5 mL) DIEA (3 eq. 6 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (2.4 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 isolated 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˜50-60%).

후처리

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

출처 및 근거

ORD 기록
ord-5cbd554d65364d76aa89d6fe80581cea
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737285B2

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