Réaction #72008

ord-2ed9b9743456472f927467f61d5c1949

Équation de réaction

CCO[C@@H]1CNCC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1.Cl
cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride
O=C(O)C(=O)c1ccccc1
benzoylformic acid
→
CCO[C@@H]1CN(C(=O)C(=O)c2ccccc2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1
title compound
Rendement 67.0%
CCO[C@@H]1CN(C(=O)C(=O)c2ccccc2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1
cis(±)-4-Chloro-N-{3-ethoxy-1-[oxo(phenyl)acetyl]piperidin-4-yl}-5-ethyl-1H-imidazole-2-carboxamide
Rendement 67.0%

Réactifs

CCO[C@@H]1CNCC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1.Cl
cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride
O=C(O)C(=O)c1ccccc1
benzoylformic acid

Réactifs

Aucun

Solvants

CN(C)C=O
DMF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol) and benzoylformic acid (45 mg, 0.30 mmol) were suspended in DMF (3 mL). The suspension was subjected to the same operation as in Example (138a) to obtain 86.2 mg of the title compound as a colorless amorphous solid (67%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08536197B2uspto-grants-2013_09