Reacción #433800

Ecuación de reacción

2-Thiophene carbonyl chloride

Compound 48

1-Benzyl-6-fluoro-2-oxo-4-(piperazin-1-yl)-1,2-dihydro-quinolin-3-carbonitrile

→

white solids

Rendimiento 76.0%

1-Benzyl-6-fluoro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

Rendimiento 76.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto come to room temperature
2. 2
   Otrothe solids formed
3. 3
   Filtraciónwere filtered
4. 4
   LavadoThe solids were washed by excess water
5. 5
   Otrodried
6. 6
   Otrorecrystallized by ethyl acetate

Procedimiento

2-Thiophene carbonyl chloride (160 μL, 1.5 mmol) was added to a stirred solution of Compound 48 (362 mg, 1.0 mmol) in pyridine (5 mL) under argon at 0° C. The solution was allowed to come to room temperature and further stirred overnight. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and recrystallized by ethyl acetate to yield 359 mg (76%) of white solids. M.P. 246° C. 1H NMR (DMSO-d6): δ 3.67 (m, 4H), 3.94 (m, 4H), 5.49 (s, 2H), 7.16 (m, 1H), 7.20–7.26 (m, 3H), 7.45 (dd, J=4.6, 9.4 Hz, 1H), 7.50 (d, J=3.9 Hz, 1H), 7.55 (td, J=2.7, 9.2 Hz, 1H), 7.66 (dd, J=2.8, 9.7 Hz, 1H), 7.80 (d, J=5.1 Hz, 1H). EIMS m/z 473 (M+1). Anal. (C26H21FN4O2S) C, H, N.

Fuente