Diisopropylethylamine → HCID 78035251, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available 5-chloro-2-pyridinecarboxylic acid (30 mg, 0.19 mmol) was dissolved in dichloromethane (3 ml) and DMF (1 ml), then diisopropylethylamine (85 μl, 0.50 mmol) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate (HATU) (87 mg, 0.23 mmol) were added at 23° C. After 15 min of stiffing tert-butyl (1SR,7SR)-1-(5-amino-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate rac-A8a) (53 mg, 0.15 mmol) was added. The brown solution was stirred for 20 hours at 23° C. The grey reaction mixture was poured on ice cold sat. NaHCO3 solution and extracted twice with dichloromethane. The organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give a brown oil which was chromatographed on 5 g silica gel with cyclohexane/ethyl acetate 1:1 to give the tert-butyl (1SR,7SR)-1-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (29 mg; 31%) as a light yellow oil. MS (ISP): m/z=491.1 [(M+H)+] and 493.2 [(M+2+H)+].

Provenance & Evidence