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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
ノート
印刷プレビュー

反応式

HRID 539016 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-af9745d036514735b53843d350443961
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08865726B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート