Dimethylformamide → (S)-3-((5-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-yl)amino)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 51a (145 mg, 0.47 mmol) in DMF (4 mL) was added DIEA (0.243 mL, 1.39 mmol) followed by (S)-3-aminopyrrolidin-2-one, HCl (70 mg, 0.51 mmol). To the stirring solution was added BOP (247 mg, 0.56 mmol) and the reaction mixture stirred at 35° C. for 18 h. The reaction mixture was diluted with EtOAc and the solution washed with saturated NH4Cl. The aqueous portion was washed with EtOAc, and the combined organic extracts washed with brine. The organic portion was dried (Na2SO4), filtered and concentrated under reduced pressure then the residue purified on silica gel chromatography eluting with 0.5 to 12% MeOH to give Compound 51b (92 mg, 50% yield) as a light orange solid. LCMS=0.75 min using analytical method (M), 396.0 (M+H). 1H NMR (400 MHz CDCl3 containing CD3OD) δ 8.02 (d, J=1.8 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.58 (dd, J=8.7, 1.9 Hz, 1H), 4.26 (dd, J=10.4, 8.4 Hz, 1H), 3.43-3.38 (m, 1H), 2.68 (dddd, J=12.6, 8.3, 6.1, 2.0 Hz, 1H), 2.18-1.96 (m, 1H).

Provenance & Evidence