Ethylenediamine → 5-(1,3-dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1H-indazol-3-amine

Temperature

50 °C

To a solution of 245 mg (0.583 mmol) 5-(1,3-dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-amine (Example 46A) in anhydrous THF (12 ml) were added 8.5 ml (8.5 mmol) tetrabutylammonium fluoride solution (1 M in THF) and ethane-1,2-diamine (200 μl). The solution was stirred at 50° C. for 3 h. After addition of further 8.5 ml tetrabutylammonium fluoride solution (1 M in THF), stirring at 50° C. was continued for 24 h. After cooling, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate solution and with water. The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. The remaining solid (200 mg, 87% of th.) was used in the next step without further purification.

1. stirringstirring at 50° C.
2. waitwas continued for 24 h
3. temperatureAfter cooling
4. concentrationthe mixture was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate
6. washwashed with saturated aqueous sodium hydrogencarbonate solution and with water
7. dry with materialThe organic layer was dried with sodium sulfate
8. filtrationfiltered
9. customevaporated to dryness
10. customThe remaining solid (200 mg, 87% of th.) was used in the next step without further purification

ORD record

ord-5aafc6647eaa428f8dd1effd3ea53266

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551989B2