Réaction #47017

ord-69913a0ea6324408a51dd9aa7a98aa5c

Équation de réaction

Cl
Hydrogen chloride
CC(C)(C)OC(=O)N1C(NCCc2ccccc2F)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
91
CC(C)(C)OC(=O)N1C(NCCc2ccccc2F)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
2-[2-(2-Fluorophenyl)ethylamino]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester
→
Cl.Fc1ccccc1CCNC1=N[C@@H](c2ccccc2)[C@@H](c2ccccc2)N1
product 92
Cl.Fc1ccccc1CCNC1=N[C@@H](c2ccccc2)[C@@H](c2ccccc2)N1
(cis-4,5-Diphenyl-4,5-dihydro-1H-imidazol-2-yl)-[2-(2-fluorophenyl)ethyl]amine hydrochloride

Réactifs

Cl
Hydrogen chloride
CC(C)(C)OC(=O)N1C(NCCc2ccccc2F)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
91
CC(C)(C)OC(=O)N1C(NCCc2ccccc2F)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
2-[2-(2-Fluorophenyl)ethylamino]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

Réactifs

Aucun

Solvants

CCOC(C)=O
EtOAc

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe solvent is removed by rotary evaporation
  2. 2
    Autrethe residue crystallized from dichloromethane and Et2O

Mode opératoire

Hydrogen chloride is bubbled into a solution of 91 (0.37 g, 0.81 mmol) in EtOAc (10 mL) for 1 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue crystallized from dichloromethane and Et2O to give 0.21 g of the product 92. 1H NMR (DMSO-d6) δ 9.10 (t, 1 H), 8.43 (s, 1 H), 8.58 (s, 1 H), 7.40 (t, 1 H), 7.30-7.15 (m, 1 H), 7.15-6.90 (m, 8 H), 6.80-6.55 (m, 4 H), 5.15 (s, 2 H), 3.80-3.45 (m, 2 H), 3.10-2.85 (m, 2 H); MS: m/z 360 (M++1).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07741493B2uspto-grants-2010_06