N-Iodosuccinimide → (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

HRID 589201노트

반응식

HRID 589201 반응식
[CH3:1][Si:2]([CH3:41])([CH3:40])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1.C1C(=O)N([I:49])C(=O)C1>CC#N>[CH3:39][Si:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][O:33][CH2:32][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:40])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:49])=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 67294324(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

생성물 1

HCID 67294877(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate (6.32 g, 10.5 mmol, preparation described previously) in CH3CN (50 mL) was added NIS (2.60 g, 11.5 mmol). The resulting solution was stirred at it for 1 h. The reaction quenched with Na2SO3 and CH3CN was evaporated. The aqueous residue was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc) to afford the titled compound as a pale yellow oil (6.94 g).

후처리

  1. customThe reaction quenched with Na2SO3 and CH3CN
  2. customwas evaporated
  3. extractionThe aqueous residue was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc)

출처 및 근거

ORD 기록
ord-de0037525a214c42bd6ff39215c6a140
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227971B2

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