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

HRID 1918676노트

반응식

HRID 1918676 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-866e90909d06454596e8b1e5eae23128
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618138B2

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