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Imidazole → Tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate

HRID 595513
ノート
印刷プレビュー

反応式

HRID 595513 の反応式
[Cl:1][C:2]1[CH:24]=[C:23]([NH:25][CH:26]([CH3:28])[CH3:27])[C:5]([C:6]([NH:8][NH:9][C:10](=[O:22])[CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][OH:13])=[O:7])=[CH:4][N:3]=1.N1C=CN=C1.[C:34]([Si:38](Cl)([CH3:40])[CH3:39])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[Si:38]([O:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[C:10]([NH:9][NH:8][C:6](=[O:7])[C:5]1[C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[CH:24][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:22])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:40])[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 131732603Tert-butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate

生成物 1

HCID 131732604Tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

tert-Butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate (53) (1 g, 2 mmol) in DCM (10 mL), imidazole (7 mmol, 3 equiv.) was added and stirred at room temperature for 10 min. Reaction mixture was cooled to 0° C., t-butyl dimethyl silyl chloride (3.6 mmol, 1.5 equiv.) was added in portions and stirred the reaction mixture overnight at room temperature. Diluted the reaction mixture using DCM, the DCM layer was washed with water. The organic layer was collected, dried over Na2SO4, filtered and concentrated to get tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate (54). LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 2.319 min; LCMS (ES-API), m/z 530.2 (M+H).

後処理

  1. customReaction mixture
  2. temperaturewas cooled to 0° C.
  3. stirringstirred the reaction mixture overnight at room temperature
  4. additionDiluted the reaction mixture
  5. washthe DCM layer was washed with water
  6. customThe organic layer was collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-6fbe87d50517432483401f7f4c5db760
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242976B2

反応ノート

読み込み中…

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