N-methyl-2-pyrrolidone → HCID 67265589, compound

Participants

Reaction Steps

To a solution of the 5-formyl-thiophen-2-yl-oxadiazol derivative (1 eq., usual scale 0.02-0.25 mmol) and the appropriate amine (2-40 eq.) in DCM (24 mL/mmol) and NMP (6 mL/mmol), sodium triacetoxy borohydride (NaBH(OAc)3) (3 eq.) is added. The mixture is stirred for 2 h before another portion of NaBH(OAc)3 (3 eq.) is added. Stirring of the suspension is continued for another 2 h and a third portion of NaBH(OAc)3 (3 eq.) is added. The mixture is stirred for 16 h before the DCM is evaporated. The remaining residue is diluted with water (4 mL/mmol) and formic acid (4 mL/mmol) and the resulting solution is separated by prep. HPLC (XBridge Prep C18, 19×50 mm, 5 μm, 10% to 95% acetonitrile in water containing 0.5% formic acid) to give the desired 5-aminomethyl-thiophen-2-yl-oxadiazol derivative as a colourless to pale yellow resin.

Provenance & Evidence