Hydrochloric Acid → 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-amine

Temperature

50 °C

2-(4H-[1,2,4]Triazol-3-yl)-isoindole-1,3-dione (1.60 g, 7.48 mmol) was dissolved in DMF (16 ml) and NaH (55% in oil, 500 mg, 11.5 mmol) and SEMCl (2.00 g, 12.0 mmol) was added thereto at room temperature. After stirring at 50° C. for 5 h, the reaction mixture was diluted with EtOAc. The mixture was poured into diluted HCl aq. and the organic layer was washed with brine, dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in THF (16 ml) and MeOH (16 ml), and hydrazine hydrate (561 mg, 11.2 mmol) was added thereto. After stirred at room temperature for 15 h, the mixture was concentrated in vacuo. The residue was suspended in EtOAc and the desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc=5/5 to 0/10) to obtain the intended compound as a colorless solid.

1. customat room temperature
2. washthe organic layer was washed with brine
3. dry with materialdried over MgSO4
4. customThe desiccant was removed through filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. dissolutionThe residue was dissolved in THF (16 ml)
7. stirringAfter stirred at room temperature for 15 h
8. concentrationthe mixture was concentrated in vacuo
9. customthe desiccant was removed through filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (hexane/EtOAc=5/5 to 0/10)

ORD record

ord-d8f60e7ff4a64fea9db26d8885b0db16

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935712B2