Réaction #61163

Équation de réaction

5-cyano-1H-pyrrole-2-carboxylic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

hydroxybenzotriazole

2-piperidinoaniline

→

title compound

Rendement 45.3%

5-Cyano-1H-pyrrole-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide

Rendement 45.3%

Solvants

brine

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (3×20 mL)
2. 2
   LavageThe organic layers were washed with brine (20 mL)
3. 3
   Séchagedried over Na2SO4
4. 4
   Autrethe solvent was removed in vacuo
5. 5
   AutrePurification of the resulting residue by silica gel preparative TLC
6. 6
   Lavageeluting with 30% ethyl acetate in hexane

Mode opératoire

To 24.5 mg (0.180 mmol) 5-cyano-1H-pyrrole-2-carboxylic acid (as prepared in the previous step) in dichloromethane (10 mL) was added 53 mg (0.28 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), hydroxybenzotriazole (HOBt, 30 mg, 0.22 mmol), and 2-piperidinoaniline (38 mg, 0.22 mmol) and the mixture stirred for 6.5 h at RT. The mixture was poured into brine (50 mL) and extracted with dichloromethane (3×20 mL). The organic layers were washed with brine (20 mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification of the resulting residue by silica gel preparative TLC eluting with 30% ethyl acetate in hexane yielded 24 mg (42%) of the title compound as a brown solid. 1H-NMR (400 MHz, CDCl3): δ 11.90 and 10.45 (br s, 1H, rotomers), 9.60 and 9.38 (s, 1H, rotomers), 8.60 and 8.47 (d, 1H, J=7.9 Hz, rotomers), 7.29-6.74 (m, 5H), 2.85 (m, 4H), 1.78-1.68 (m, 6H). LC-MS (ESI, m/z): Calcd. for C17H19N4O, 295.2 (M+H); found: 295.2.

Source