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Trifluoroacetic acid → [6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone

HRID 1786462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1786462
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([CH:32]4[CH2:34][CH2:33]4)(=[O:31])=[O:30])[CH2:25][CH2:24]3)=[O:22])[N:8]2[CH2:11][CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[O:35][CH:36]1[CH2:41][CH2:40][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:38][CH2:37]1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([CH:32]4[CH2:34][CH2:33]4)(=[O:30])=[O:31])[CH2:25][CH2:24]3)=[O:22])[N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[O:35][CH:36]1[CH2:37][CH2:38][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:40][CH2:41]1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68566693[6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone

Produkt 1

HCID 68566618[6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanoneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 85 mg (0.12 mmol) [6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone in 2 mL dichloromethane was cooled to 0° C. and 1.0 mL (1.49 g, 13.1 mmol) trifluoroacetic acid were added. The cooling bath was removed and after stirring for 1 h at room temperature the solution was evaporated to dryness. The residue was taken up in dichloromethane and extracted with 1M aqueous sodium hydroxide solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated to afford 71 mg (99%) of the title compound as colourless oil.

Aufarbeitung

  1. customThe cooling bath was removed
  2. customwas evaporated to dryness
  3. extractionextracted with 1M aqueous sodium hydroxide solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5cd740228ca8414e86fd02cc422b5198
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07507736B2

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