반응 #970235

반응 방정식

3-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid

1-benzyl-1H-pyrazol-3-ylamine

→

N-(1-Benzyl-1H-pyrazol-3-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide

수율 45.0%

용매

thionylchloride

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   기타the solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue is dissolved in dichloromethane (1.2 ml)
4. 4
   workup.ADDITIONethyldiisopropyl-amine (167 μl) is added
5. 5
   추출The reaction solution is extracted with water
6. 6
   세척The organic layer is washed with brine
7. 7
   건조dried over MgSO4
8. 8
   기타the solvent is removed in vacuo

실험 절차

3-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid (0.672 mmol) is dissolved in thionylchloride (1.2 ml) and heated to 70° C. for 1 hour. After cooling to room temperature, the solvent is removed in vacuo. The residue is dissolved in dichloromethane (1.2 ml) and ethyldiisopropyl-amine (167 μl) is added and 1-benzyl-1H-pyrazol-3-ylamine (1.2 eq) is added. The solution is stirred 21 hours at room temperature. The reaction solution is extracted with water. The organic layer is washed with brine and dried over MgSO4 and the solvent is removed in vacuo. N-(1-Benzyl-1H-pyrazol-3-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide is isolated after column chromatography (heptan /ethylacetate) as yellow oil in a yield of 45%; HPLC (method B): 3.63 min; LC-MS (method B): 2.74 min, 462.2 (MH+); 1H-NMR (DMSO-d5, 500 MHz): δ [ppm] 10.78 (s, 1), 7.79 (d, 1H, J=2.2 Hz), 7.468 (dd, 1H, J=3 Hz, J=4.9 Hz), 7.359-7.269 (m, 4H), 7.245-7228 (m, 2H), 7.174-7.139 (m, 2H), 7.11 (dd, 1H, J=1.1 Hz, J=4.9 Hz), 6.648 (d, 1H, J=2.2 Hz), 5.256 (s, 2H), 4.678 (sep, 1H, J=6 Hz), 4.223 (t, 2H, J=6.9 Hz), 3.049 (t, 2H, J=6.9 Hz), 1.262 (d, 6H, J=6 Hz).

출처