Diisopropylethylamine → HCID 66622465, compound

Participants

Reaction Steps

To a solution of isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-5-oxo-pentyl ester (75 mg crude mixture, 0.15 mmol) in anhydrous DCE (2 mL) and DIEA (56 uL, 0.32 mmol) was added the triazolopiperazine HCl salt (27 mg, 0.17 mmol) at RT. After 5 min of stirring at RT, sodium triacetoxyborohydride (98 mg, 0.45 mmol) was added in one portion. The slurry was stirred for 16 h at RT, the diluted in CH2Cl2 and washed with saturated aq. NaHCO3 and brine. After drying the solution over Na2SO4, the reaction mixture was concentrated and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-5-(5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-pentyl ester (30 mg, 30%) LRMS (M+H+) m/z 595.2.

Provenance & Evidence