N-Methylbenzylamine → 2-(4-bromo-1H-pyrazol-1-yl)-N-methyl-N-(phenylmethyl)ethanamine

Temperatur

80 °C

4-bromo-1-(2-chloroethyl)-1H-pyrazole (317 mg, 1.513 mmol, for a preparation see Intermediate 54) was dissolved in N,N-dimethylformamide (DMF) (5 mL) and cesium carbonate (740 mg, 2.270 mmol) added with N-methyl-1-phenylmethanamine (0.973 mL, 7.57 mmol, available from Aldrich). The mixture was heated to 80° C. for 3 hours then allowed to stir at 80° C. overnight. The mixture was cooled to room temperature and loaded on to a 20 g SCX cartridge. The SCX was eluted with MeOH (100 ml) and 2M methanolic ammonia (100 ml). The basic fraction was evaporated to a colourless oil, loaded on to a 25+M Biotage silica column and eluted with a gradient of 0 to 2.5% 2M methanolic ammonia in DCM. The product containing fractions were evaporated to a pale yellow oil (155 mg). LCMS (Method C): Rt=0.67, MH+=294

1. temperatureThe mixture was cooled to room temperature
2. washThe SCX was eluted with MeOH (100 ml) and 2M methanolic ammonia (100 ml)
3. customThe basic fraction was evaporated to a colourless oil
4. washeluted with a gradient of 0 to 2.5% 2M methanolic ammonia in DCM
5. additionThe product containing fractions
6. customwere evaporated to a pale yellow oil (155 mg)

ORD-Eintrag

ord-a136d9bc00aa4b9da7a3e6aa93946b89

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08697725B2