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(2-Aminoethoxy)(tert-butyl)dimethylsilane → (S)-N1-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methyl-N2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)butane-1,2-diamine

HRID 539016
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HRID 539016 반응식
[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:24]=[CH:25][N:26]=4)=[CH:18][CH:17]=3)=[C:9]2[N:8]=1)[CH:4]=O.[Si:36]([O:43][CH2:44][CH2:45][NH2:46])([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C1COCC1>[Si:36]([O:43][CH2:44][CH2:45][NH:46][CH2:4][C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])[CH:24]=[CH:25][N:26]=4)=[CH:18][CH:17]=3)=[C:9]2[N:8]=1)[CH:2]([CH3:35])[CH3:1])([C:39]([CH3:41])([CH3:42])[CH3:40])([CH3:38])[CH3:37]
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참가 물질

6

반응물 3

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 5049666Sodium triacetoxyborohydrideHCID 86667823(S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal

생성물 1

HCID 68088943(S)-N1-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methyl-N2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)butane-1,2-diamine

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal (27 mg, 0.055 mmol) in DCE (1 mL) was added a solution of 2-(tert-butyldimethylsilyloxy)ethanamine (29 mg, 0.17 mmol) in THF (0.2 mL). The reaction was allowed to stir at ambient temperature for 15 minutes, at which point Na(OAc)3BH was added and the reaction allowed to stir at ambient temperature for 2 hours. The reaction mixture was partitioned between saturated aqueous NaHCO3 and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined extracts were washed with brine, dried and concentrated to give (S)—N1-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methyl-N2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)butane-1,2-diamine. The crude was used in the next step without further purification. LCMS (APCI+) m/z 650.9 [M+H]+.

후처리

  1. additionwas added
  2. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af9745d036514735b53843d350443961
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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