Trimethylaluminum → HCID 178462529, Verbindung

A 2M solution of trimethylaluminium in toluene (0.413 mL, 0.83 mmol), was added drop-wise to a suspension of methyl 4-(1-ethylpiperidin-4-yl)benzoate (0.082 g, 0.33 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.082 g, 0.33 mmol) in toluene (2 mL) at room temperature. The solution was then heated at 60° C. for 18 h. The reaction mixture was cooled, quenched with methanol (2 ml) and 2N hydrochloric acid (1 ml). The reaction mixture was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.058 g, 38.0%) as a white solid.

1. temperatureThe reaction mixture was cooled
2. customquenched with methanol (2 ml) and 2N hydrochloric acid (1 ml)
3. customThe reaction mixture was purified by ion exchange chromatography
4. washThe desired product was eluted from the column
5. customwere evaporated to dryness
6. customThe crude product was purified by preparative HPLC
7. additionFractions containing the desired compound
8. customwere evaporated to dryness

ORD-Eintrag

ord-37c735125f524b8fa3ea042232e2ba59

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08604022B2