Reacción #10898

Ecuación de reacción

1,1-dimethylethyl ester

4-[4-[[4-Amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]-1-piperazinecarboxyli acid, 1,1-dimethylethyl ester

TFA CH2Cl2

→

[4-amino-2-[[4-(1-piperazinyl)phenyl]amino]-5-thiazolyl](3-fluorophenyl)methanone

Rendimiento 100.6%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solution was evaporated in vacuo
2. 2
   workup.ADDITIONTo the residue was added resin-bound N,N-diisopropylethylamine (2.5 g, loading capacity: 3.8 mmol/g from Argonaut, Inc.) and CH2Cl2 (15 mL)
3. 3
   Filtraciónthe mixture was filtered
4. 4
   Lavadowashed successively with CH3OH and CH2Cl2
5. 5
   OtroThe solvent was evaporated in vacuo
6. 6
   Otrothe residue was triturated by diethyl ether/hexanes (1/9)

Procedimiento

A mixture of 4-[4-[[4-amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]1-piperazinec acid, 1,1-dimethylethyl ester (75 mg, 0.15 mmol) (from Step A above) and a solution of TFA/CH2Cl2 (1:1; 1.5 mL) was gently shaken for 1.5 h. The solution was evaporated in vacuo. To the residue was added resin-bound N,N-diisopropylethylamine (2.5 g, loading capacity: 3.8 mmol/g from Argonaut, Inc.) and CH2Cl2 (15 mL). After shaking overnight, the mixture was filtered and washed successively with CH3OH and CH2Cl2. The solvent was evaporated in vacuo and the residue was triturated by diethyl ether/hexanes (1/9) to afford [4-amino-2-[[4-(1-piperazinyl)phenyl]amino]-5-thiazolyl](3-fluorophenyl)methanone (60 mg, 100%).

Fuente