반응 #1869174

반응 방정식

NaHCO3

2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethylamine hydrochloride

triethylamine

acetic anhydride

→

title product

수율 92.0%

N-(2-{1-[(6-Chloro-imidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}-ethyl)acetamide

수율 92.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   추출extracted with dichloromethane
2. 2
   건조dried over MgSO4
3. 3
   농축concentrated in vacuo to a foam
4. 4
   workup.ADDITIONThe foam is treated with 20:80 ethyl acetate
5. 5
   농축hexane and concentrated in vacuo to a solid
6. 6
   기타This is triturated with ether
7. 7
   여과filtered
8. 8
   기타The filtercake is dried

실험 절차

A stirred mixture of 2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethylamine hydrochloride, 417 mg, 1.00 mmol) in dichloromethane and triethylamine (0.40 mL, 3.0 mmol) is treated with catalytic 4-dimethylaminopyridine (DMAP) (˜5 mg) at room temperature under nitrogen. The heterogeneous mixture is treated with acetic anhydride (0.30 mL, 3.2 mmol) and the reaction becomes homogeneous. After 16 h, the reaction is treated with saturated aqueous NaHCO3 (8 mL) for 0.3 h and then extracted with dichloromethane. The extracts are combined, dried over MgSO4 and concentrated in vacuo to a foam. The foam is treated with 20:80 ethyl acetate:hexane and concentrated in vacuo to a solid. This is triturated with ether and filtered. The filtercake is dried to afford the title product as a white solid, 389 mg (92% yield), mp 150-152° C., characterized by CHN elemental analysis and 1H NMR.

출처