Trifluoroacetic acid → 5-amino-N-(2-(5-chloro-1H-indol-3-yl)ethyl)isoxazole-3-carboxamide

HRID 58685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58685
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1[CH:20]=[C:19]([NH:21]C(=O)OC(C)(C)C)[O:18][N:17]=1)=[O:15].FC(F)(F)C(O)=O>ClCCl>[NH2:21][C:19]1[O:18][N:17]=[C:16]([C:14]([NH:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][CH:6]=2)=[O:15])[CH:20]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 66831951tert-butyl 3-(2-(5-chloro-1H-indol-3-yl)ethylcarbamoyl)isoxazol-5-ylcarbamate

Produkt 1

HCID 668319505-amino-N-(2-(5-chloro-1H-indol-3-yl)ethyl)isoxazole-3-carboxamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-(2-(5-chloro-1H-indol-3-yl)ethylcarbamoyl)isoxazol-5-ylcarbamate (0.400 g; 0.988 mmol) in dichloromethane (8 mL) was added trifluoroacetic acid (2 mL). The mixture was stirred at room temperature for 4 h and was then evaporated to dryness to remove the excess of TFA. The residue was dissolved in dichloromethane and the solution was washed with an aqueous solution of sodium carbonate. The organic layer was evaporated and the crude material was purified by flash chromatography on silica gel (eluent: 1 to 10% methanol in dichloromethane) to afford 0.207 g (69%) of 5-amino-N-(2-(5-chloro-1H-indol-3-yl)ethyl)isoxazole-3-carboxamide as a solid.

Aufarbeitung

  1. customwas then evaporated to dryness
  2. customto remove the excess of TFA
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe solution was washed with an aqueous solution of sodium carbonate
  5. customThe organic layer was evaporated
  6. customthe crude material was purified by flash chromatography on silica gel (eluent: 1 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cda6d69232de40d6869e8e5f72eabf3b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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