Réaction #47014

ord-e780e390a62e483688f5d057b78ce16a

Équation de réaction

Cl
Hydrogen chloride
CC(C)(C)OC(=O)N1C(NCc2cccc(F)c2)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
87
CC(C)(C)OC(=O)N1C(NCc2cccc(F)c2)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
2-(3-Fluorobenzylamino)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester
→
Cl.Fc1cccc(CNC2=N[C@@H](c3ccccc3)[C@@H](c3ccccc3)N2)c1
product 88
Cl.Fc1cccc(CNC2=N[C@@H](c3ccccc3)[C@@H](c3ccccc3)N2)c1
(cis-4,5-Diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(3-fluorobenzyl)amine hydrochloride

Réactifs

Cl
Hydrogen chloride
CC(C)(C)OC(=O)N1C(NCc2cccc(F)c2)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
87
CC(C)(C)OC(=O)N1C(NCc2cccc(F)c2)=N[C@@H](c2ccccc2)[C@H]1c1ccccc1
2-(3-Fluorobenzylamino)-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 87 (1.5 g, 3.37 mmol) in EtOAc (30 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 1.05 g of the product 88. 1H NMR (DMSO-d6) δ 9.28 (t, 1 H), 8.68 (s, 1 H), 8.15 (s, 1 H), 7.35-7.10 (m, 3 H), 7.10-6.80 (m, 7 H), 6.80-6.50 (m, 4 H), 5.03 (s, 1 H), 4.80-4.45 (m, 2 H); MS: m/z 346 (M++1).

Source

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