Reacción #47198

Ecuación de reacción

4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3-ethyl-3-methylpiperazin-2-one

1,2-dichloro-3-isocyanatobenzene

→

1-(5-tert-butyl-3-(2-ethyl-2-methyl-3-oxopiperazine-1-carbonyl)thiophen-2-yl)-3-(2,3-dichlorophenyl)urea

Rendimiento 44.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Otrosolvent was removed under reduced pressure
3. 3
   Otrothe crude product purified by preparative TLC

Procedimiento

To 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3-ethyl-3-methylpiperazin-2-one (72.0 mg, 0.22 mmol) in THF (2 mL) was added 1,2-dichloro-3-isocyanatobenzene (50.0 mg, 0.27 mmol). The resulting reaction mixture was stirred at room temperature and the reaction progress monitored by SFC-MS. When the reaction was completed, solvent was removed under reduced pressure and the crude product purified by preparative TLC to afford 1-(5-tert-butyl-3-(2-ethyl-2-methyl-3-oxopiperazine-1-carbonyl)thiophen-2-yl)-3-(2,3-dichlorophenyl)urea (50 mg, 44%) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 9.93 (s, 1H), 9.52 (s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.26-7.22 (m, 2H), 6.46 (s, 1H), 3.62-3.58 (m, 1H), 3.40-3.35 (m, 1H), 3.30-3.23 (m, 1H), 3.19-3.13 (m, 1H), 2.65-2.61 (m, 1H), 1.89-1.85 (m, 1H), 1.58 (s, 3H), 1.22 (s, 9H), 0.69 (t, J=7.4 Hz, 3H).

Fuente