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

HRID 58685ノート

反応式

HRID 58685 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cda6d69232de40d6869e8e5f72eabf3b
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

反応ノート

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