反応 #68673

反応方程式

(Z)-tert-butyl (6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

ethynylcyclopropane

potassium hydrogencarbonate

→

title compound

収率 23.2%

(6-(5-cyclopropylisoxazol-3-yl)-[1,2,4]-triazolo-[4,3-b]pyridazin-3-yl)methanamine

収率 23.2%

溶媒

EtOAc

反応条件

後処理

1. 1
   その他to afford the protected intermediate
2. 2
   その他The solvent was removed by rotary evaporation
3. 3
   workup.DISSOLUTIONthe residue was redissolved in dicholoromethane (5 mL) and TFA (2 mL)
4. 4
   その他The solvent was then removed
5. 5
   workup.DISSOLUTIONthe residue was redissolved in MeOH
6. 6
   workup.ADDITIONSolid K2CO3 was added
7. 7
   workup.STIRRINGthe mixture was stirred for 1 h to free base the title compound
8. 8
   その他Purified the amine via MPLC (DCM/MeOH+1% NH4OH)

実験手順

Dissolved (Z)-tert-butyl (6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (110 mg, 337 μmol), ethynylcyclopropane (28 μl, 337 μmol), and potassium hydrogencarbonate (67.4 mg, 673 μmol) in 0.3 mL of EtOAc and heated to 60° C. for 12 h to afford the protected intermediate. The solvent was removed by rotary evaporation and the residue was redissolved in dicholoromethane (5 mL) and TFA (2 mL) and stirred for 30 min at room temperature. The solvent was then removed and the residue was redissolved in MeOH. Solid K2CO3 was added and the mixture was stirred for 1 h to free base the title compound. Purified the amine via MPLC (DCM/MeOH+1% NH4OH) to afford the title compound (20 mg, 23% yield).

出典