Trifluoroacetic acid → 5-amino-N-(2-(5-chloro-1H-indol-3-yl)ethyl)isoxazole-3-carboxamide
Reaction equation
[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]=1Participants
4
Procedure
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.
Workup
- customwas then evaporated to dryness
- customto remove the excess of TFA
- dissolutionThe residue was dissolved in dichloromethane
- washthe solution was washed with an aqueous solution of sodium carbonate
- customThe organic layer was evaporated
- customthe crude material was purified by flash chromatography on silica gel (eluent: 1 to 10% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-cda6d69232de40d6869e8e5f72eabf3b
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Reaction notes
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