Diisopropylethylamine → HCID 66977626, Verbindung

Temperatur

35 °C

Method G—Step a To a mixture of 1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-pyrrolidine-3-carboxylic acid (obtained as described in general method 2, step e) (0.01 g, 0.26 mmol) in dcm (4 mL), HATU (0.10 g, 0.29 mmol), diisopropylethylamine (DIPEA) (0.14 mL, 0.76 mmol) and tert-butyl-1-piperazine carboxylate (0.06 g, 0.32 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature and washed with water (2×5 mL) and saturated Na2CO3 solution (2×5 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to obtain a crude that was triturated with diethylether (3 mL), filtered and dried. The precipitate was then purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:NH3 in MeOH (2M)/4:0.8), and then a filtration on an SCX cartridge was run (eluent gradient: DCM:MeOH/1:1 to NH3 in MeOH), to obtain 0.11 g of the title compound (67%).

1. additionwere added
2. temperaturecooled to room temperature
3. washwashed with water (2×5 mL) and saturated Na2CO3 solution (2×5 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customto obtain a crude that
8. customwas triturated with diethylether (3 mL)
9. filtrationfiltered
10. customdried
11. customThe precipitate was then purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:NH3 in MeOH (2M)/4:0.8)
12. filtrationa filtration on an SCX cartridge

ORD-Eintrag

ord-72d4ca0834ca4ae9be78011979c74bf5

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08835648B2