Diisopropylethylamine → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

HRID 884052노트

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HRID 884052 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])/[C:12]([OH:14])=O)=[CH:7][CH:6]=1.Cl.Cl.[CH3:26][N:27]([CH3:38])[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:26][N:27]([CH3:38])[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:12](=[O:14])/[C:11](/[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:33][CH:32]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 574247414-[2-(Dimethylamino)ethoxy]aniline dihydrochlorideHCID 57693045(E)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enoic acid

생성물 1

HCID 57693048(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide수율 65%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a mixture of 3 (2.90 g, 9.28 mmol), 4-(2-(dimethylamino)ethoxy)benzenamine dihydrochloride (2.58 g, 10.2 mmol), 4-Dimethylaminopyridine (56.7 mg, 0.464 mmol) in CH2Cl2 (100 ml) was added O-Benzotriazoyl-N,N,N′,N′-tetramethyluronium Hexafluorophosphate (3.87 g, 10.2 mmol) under ice cooling, and the mixture was stirred at 0° C. for 10 min. Then N,N-Diisopropylethylamine (4.19 g, 32.4 mmol) was added under ice cooling. The mixture was stirred at 0° C. for 5 min, and at room temperature for 15 h. The reaction was quenched with saturated aqueous NaHCO3 under ice cooling, and the whole was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by Biotage (eluent: CH2Cl2 to CH2Cl2/MeOH, 6:1) gave the colorless solid. The solid was triturated with Et2O-hexane to give 4 (65%).

후처리

  1. stirringThe mixture was stirred at 0° C. for 5 min
  2. waitat room temperature for 15 h
  3. customThe reaction was quenched with saturated aqueous NaHCO3 under ice cooling
  4. extractionthe whole was extracted with CHCl3
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by Biotage (eluent: CH2Cl2 to CH2Cl2/MeOH, 6:1)
  9. customgave the colorless solid
  10. customThe solid was triturated with Et2O-hexane

출처 및 근거

ORD 기록
ord-bd615208740641bb90c3637a809a53e5
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236987B2

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