(S)-tert-butyl 1-(3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethylcarbamate → tert-Butyl (S)-(1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170382노트

반응식

HRID 2170382 반응식
[Br:1][C:2]1[C:3]([C@@H:19]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)=[N:4][CH:5]=[C:6]([N:8]2C(=O)C3C(=CC=CC=3)C2=O)[CH:7]=1>C(O)C.O.NN>[NH2:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([C@@H:19]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)=[N:4][CH:5]=1

참가 물질

4

반응물 1

HCID 90281392(S)-tert-butyl 1-(3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethylcarbamate

생성물 1

HCID 90290195tert-Butyl (S)-(1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 24654Hydrazine hydrate (1:1)용매

실험 절차

To a mixture of (S)-tert-butyl (1-(3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (30E, 1.5 g, 2.7 mmol) in 27 ml of ethanol, 0.9 ml of hydrazine monohydrate was added and stirred at room temperature for 2 hours. To the reaction mixture, ethanol was added and filtrated, and the filtrate was concentrated. The residue was diluted with ethyl acetate, and washed with water and then with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give the title product. MS (m/z) 427.83 [M+H]+.

후처리

  1. additionwas added
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-55789e97ab8e44269a50700fb17bb58a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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