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4-Chloroaniline → 2-(4-Bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide

HRID 220193
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HRID 220193 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][N:13]2[CH2:17][CH2:16][CH:15](N(CC)CC)[CH2:14]2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Cl:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH:17]2[N:25]([CH2:26][CH3:28])[CH2:29][CH3:31])[C:9]([NH:63][C:60]2[CH:61]=[CH:62][C:57]([Cl:56])=[CH:58][CH:59]=2)=[O:11])=[CH:6][CH:7]=1
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반응물 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 592382652-(4-Bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid

생성물 1

HCID 672315242-(4-Bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 2-(4-bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid (590 mg, 1.6 mmol), DIPEA (1.03 g, 8 mmol), and Pybrop (1.12 g, 2.4 mmol) in CH2Cl2 (10 mL) was added 4-chloro-phenylamine (306 mg, 2.4 mmol). This mixture was stirred overnight at room temperature and then evaporated. The mixture redissolved in EtOAc (20 mL) and washed with water, brine, dried with Na2SO4, concentrated in vacuo. The residue was purified by flash column chromatography to give a white solid. MS: calc'd 478 (MH+), exp 478 (MH+).

후처리

  1. customevaporated
  2. dissolutionThe mixture redissolved in EtOAc (20 mL)
  3. washwashed with water, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. customto give a white solid

출처 및 근거

ORD 기록
ord-b9be3c2ad4224679ae5953d8dd11722f
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202866B2

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