Cesium carbonate → {3-[3-(5-Acetyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propyl}-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

Cesium carbonate [534-17-8] (125 mg, 0.4 mmol) was added to a solution of 1-[5-(6-fluoro-imidazo[1,2-b]pyridazin-3-yl)-thiophen-2-yl]-ethanone (50 mg, 0.2 mmol) and N-(3-aminopropyl)-N-methylcarbamic acid tert-butyl ester [150349-36-3] (72 mg, 0.4 mmol) in N,N-dimethylformamide (1.5 mL) and stirred overnight at ambient temperature then partitioned between ethyl acetate and water. The organic extract was evaporated and product isolated by preparative RP-HPLC to provide {3-[3-(5-acetyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propyl}-methyl-carbamic acid tert-butyl ester as a yellow oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.33-1.49 (m, 9H) 2.04 (d, J=11.87 Hz, 2H) 2.59 (s, 3H) 2.91 (s, 3H) 3.35-3.53 (m, 4H) 4.62 (s, 1H) 6.75 (d, J=9.60 Hz, 1H) 7.64-7.75 (m, 2H) 7.87 (d, J=4.04 Hz, 1H) 7.98 (s, 1H). LRMS (ESI) m/z 430.2 [(M+H)]+, calc'd for C21H27N5O3S: 429.55.

Provenance & Evidence