Trimethylaluminum → HCID 178489767, Verbindung

Temperatur

60 °C

A 2M solution of trimethylaluminium (2.500 mL, 5.00 mmol) in toluene, was added dropwise to a stirred suspension of ethyl 4-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)benzoate (0.643 g, 2 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.495 g, 2.00 mmol) in toluene (10 mL) at room temperature. The solution was then heated at 60° C. for 18 h. The reaction mixture was cooled and quenched with methanol (15 ml) and 2N hydrochloric acid (5 ml). The crude reaction mixture was purified by ion exchange chromatography on a SCX column, eluting with 7N ammonia in methanol. The appropriate fractions were evaporated to give an oil. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% 2.5N ammonia/MeOH in DCM. Pure fractions were evaporated to dryness to afford, on crystallisation from DCM/diethyl ether, the title compound (0.322 g, 33.7%) as a cream solid.

1. temperatureThe reaction mixture was cooled
2. customquenched with methanol (15 ml) and 2N hydrochloric acid (5 ml)
3. customThe crude reaction mixture
4. customwas purified by ion exchange chromatography on a SCX column
5. washeluting with 7N ammonia in methanol
6. customThe appropriate fractions were evaporated
7. customto give an oil
8. customThe crude product was purified by silica column chromatography
9. washeluting with a gradient of 0 to 10% 2.5N ammonia/MeOH in DCM
10. customPure fractions were evaporated to dryness
11. customto afford, on crystallisation from DCM/diethyl ether

ORD-Eintrag

ord-3c733f1e59bb414aa5d4f88bc9293621

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129391B2