반응 #547441

반응 방정식

ethyl 2-(4-sulfamoyl-phenyl)-1,3-thiazole-4-carboxylic acid

TFA

(PhO)2PON3

6-(piperidylmethyl)-2-pyridylamine

→

title compound

4-{4-[3-(6-Piperidin-1-ylmethyl-pyridin-2-yl)-ureido]-thiazol-2-yl}-benzenesulfonamide

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도to reflux for 4 h
3. 3
   세척The mixture was washed with 10% HCl (aq)
4. 4
   추출extracted with EtOAc (3×10 mL)
5. 5
   추출extracted with CH2Cl2 (3×20 mL)
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated by rotary evaporation
8. 8
   기타purified on silica gel (2:1 hexanes/EtOAc and 1:1 MeOH/CH2Cl2)

실험 절차

To a stirred solution of ethyl 2-(4-sulfamoyl-phenyl)-1,3-thiazole-4-carboxylic acid (90 mg, 0.32 mmol) in dry TFA (3 mL) and 4A molecular sieves at RT and under N2 was added TEA (0.1 mL). After 5 min, (PhO)2PON3 (0.11 mL) and 6-(piperidylmethyl)-2-pyridylamine (0.10 g, 0.51 mmol) were added and the reaction mixture was heated to reflux for 4 h and then cooled to RT. The mixture was washed with 10% HCl (aq) and extracted with EtOAc (3×10 mL). The aqueous layer was brought to a pH 8.0 and extracted with CH2Cl2 (3×20 mL). The extracts were combined, dried over MgSO4, concentrated by rotary evaporation and purified on silica gel (2:1 hexanes/EtOAc and 1:1 MeOH/CH2Cl2) to afford the title compound as a pale yellow solid. EI-MS m/z 473 (M+H). Calc'd for C21H24N6O3S2: 472.14.

출처