Nitrogen → 8-Chloro-3-cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

Participants

Reaction Steps

In an oven-dried flask filled with N2 was added cyclopentanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide (80 mg, 0.2 mol), MeCN (5 mL) and DMF (0.9 mL). POCl3 was added dropwise at 0° C. The reaction was warmed up to rt and stirred at that temp overnight. The excess of POCl3 was removed under reduced pressure and the residue was quenched with 2 N NH3 in i-PrOH at 0° C. with vigorous stirring to adjust pH to 9. The crude reaction mixture was then charged with water and the aqueous layer was washed with DCM. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to obtain 42 mg of the title compound as a yellow oil. Compound was carried over to the next step. MS (ES+): m/z 389.88 (30)[MH+]. HPLC: tR=4.29 min (Open Lynx, polar—5 min).

Provenance & Evidence