Chloroform → HCID 58087997, compound

Participants

Reaction Conditions

Reaction Steps

To N-(2-(1H-imidazole-1-carbothioamido)benzo[d]thiazol-6-yl)acetamide (300 mg, 0.95 mmol) in N,N-dimethylformamide (10 mL) was added (S)-3-(aminomethyl)quinuclidin-3-ol, 2HCl (238 mg, 1 mmol) and triethylamine (0.39 mL, 2.84 mmol). The reaction was heated to 80° C. for 3 hours. N,N′-diisopropylcarbodiimide (0.59 mL, 3.78 mmol) was then added to the reaction mixture. The mixture was heated at 80° C. for another 2 hours. The reaction was cooled, then chloroform and water were added to the mixture. The organic layer concentrated in vacuo to yield crude product. The crude material was purified via flash chromatography (2-20% [10% ammonium hydroxide/methanol-chloroform). The product fractions were then triturated with ether to yield (R)—N-(2-(4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]-2-ylamino)benzo[d]thiazol-6-yl)acetamide (144.5 mg, 0.39 mmol, 41.2% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.98 (1H, s), 8.93 (1H, br. s.), 8.12 (1H, d, J=1.83 Hz), 7.52 (1H, d, J=8.42 Hz), 7.38 (1H, dd, J=8.60, 2.01 Hz), 3.88 (1H, d, J=9.88 Hz), 3.62 (1H, d, J=9.88 Hz), 3.02 (2H, s), 2.74-2.85 (2H, m), 2.66 (2H, t, J=7.68 Hz), 2.05 (4H, s), 1.91 (1H, br. s.), 1.41-1.64 (3H, m). MS (LC/MS) R.T.=1.55; [M+H]+=372.2.

Provenance & Evidence