반응 #165013

반응 방정식

4-benzyloxy-phenyl-acetohydroximoyl chloride

3-ethynyl-pyridin-2,6-diamine

triethylamine

→

title compound

수율 27.0%

3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamine

수율 27.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was then stirred for further 1.5 hours at 55° C
2. 2
   온도The reaction solution was cooled to room temperature
3. 3
   농축concentrated under a reduced pressure
4. 4
   여과The residue was filtered by NH silica gel column chromatography (ethyl acetate)
5. 5
   기타to obtain a crude product
6. 6
   기타The crude product was purified by reverse-phase high performance liquid chromatography (
7. 7
   workup.ADDITIONcontaining 0.1% trifluoroacetic acid)
8. 8
   기타The solvent was evaporated under a reduced pressure
9. 9
   여과the residue was filtered with NH silica gel

실험 절차

To a mixture of 4-benzyloxy-phenyl-acetohydroximoyl chloride (140 mg, 0.51 mmol) described in Manufacturing Example 1-1-3 and tetrahydrofuran (10 mL) were added 3-ethynyl-pyridin-2,6-diamine (102 mg, 0.76 mmol) described in Manufacturing Example 13-1-3 and triethylamine (0.71 mL, 5.1 mmol), which was stirred overnight at room temperature. The reaction mixture was then stirred for further 1.5 hours at 55° C. The reaction solution was cooled to room temperature and concentrated under a reduced pressure. The residue was filtered by NH silica gel column chromatography (ethyl acetate) to obtain a crude product. The crude product was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid). The solvent was evaporated under a reduced pressure, and the residue was filtered with NH silica gel to obtain the title compound (51 mg, 27%).

출처