반응 #1834507

반응 방정식

1,8-diazabicyclo[5,4,0]undec-7-ene

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid

1,1′-carbonyl diimidazole

HCl

benzenesulfonamide

→

N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionyl}-benzenesulfonamide

수율 60.0%

용매

water

THF

반응 조건

후처리

1. 1
   온도After the mixture is cooled down to room temperature
2. 2
   workup.STIRRINGThe mixture is stirred for 5 hr at room temperature
3. 3
   추출The mixture is extracted with EtOAc (3×50 mL)
4. 4
   기타dried
5. 5
   농축concentrated
6. 6
   기타to give crude product
7. 7
   기타Purification by preparative TLC

실험 절차

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid (150 mg, 0.41 mmol) is dissolved in dry THF (3.0 mL) and 1,1′-carbonyl diimidazole (150 mg, 0.92 mmol) is added into it at room temperature. The mixture is stirred for 30 min and then it is heated at 55° C. for 1 hr. After the mixture is cooled down to room temperature, benzenesulfonamide (130 mg, 0.82 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.12 mL, 0.82 mmol) is added. The mixture is stirred for 5 hr at room temperature and then 1.0 M HCl (3 mL) is added followed by water (30 mL). The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC using 75% EtOAc in Hexanes affords 123 mg (60%) of N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionyl}-benzenesulfonamide. LCMS (ESMS): m/z 506.18 (M+H+).

출처