反应 #61163

反应方程式

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

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

hydroxybenzotriazole

2-piperidinoaniline

→

title compound

收率 45.3%

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

收率 45.3%

溶剂

brine

dichloromethane

反应条件

后处理

1. 1
   萃取extracted with dichloromethane (3×20 mL)
2. 2
   洗涤The organic layers were washed with brine (20 mL)
3. 3
   干燥dried over Na2SO4
4. 4
   其他the solvent was removed in vacuo
5. 5
   其他Purification of the resulting residue by silica gel preparative TLC
6. 6
   洗涤eluting with 30% ethyl acetate in hexane

实验过程

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.

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