1,2-Dichloroethane → HCID 57476548, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml flask was added 2-(tert-butoxycarbonyl-amino)benzo[d]thiazole-6-carboxylic acid (1.0 g, 3.4 mmol) and pyrrolidine (0.559 mL, 6.8 mmol) in tetrahydrofuran (50 mL). To this solution was added EDC (1.3 g, 6.8 mmol), 1-hydroxybenzotriaxole (1.041 g, 6.8 mmol) and Hunig's Base (2.37 mL, 13.59 mmol). The reaction was stirred at 25° C. for 1 hour. The reaction was then poured into water and dichloromethane. The water was extracted 3 times with dichloromethane and the organic layers were combined and concentrated. The residue was taken up in a small amount of dichloromethane and precipitated out with diethyl ether/hexanes. The flask was put in the freezer for 1 hour and filtered. The white precipitate was collected to yield tert-butyl 6-(pyrrolidine-1-carbonyl)benzo[d]thiazol-2-ylcarbamate (1.09 g, 3.14 mmol, 92% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.95 (s, 1 H), 8.14 (s, 1 H), 7.61-7.77 (m, J=8.39, 1.98 Hz, 1 H), 7.46-7.63 (m, 1 H), 3.39-3.63 (m, 4 H), 1.74-2.00 (m, 4 H), 1.45-1.62 (m, 9 H). MS (LC/MS) R.T.=3.40; [M+H]+=363.1.

Provenance & Evidence