HCID 178478079, compound → HCID 178420219, compound

HRID 1028197Notes

Reaction equation

HRID 1028197 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]([C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1>CCO.[Pd]>[C:4]1([CH:8]([C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 178478079HCID 178478079, compound

Product 1

HCID 178420219HCID 178420219, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(1-(3-chlorophenyl)-2-phenylvinyl)-1H-imidazole (AGN-216677) (35 mg) in EtOH (10 mL) was reduced by the action of 10% Pd/C (20 mg) under H2 atmosphere forl 6 h at rt. The mixture was filtered through Celite and freed of solvent under reduced pressure. The residue was purified by chromatography on silica gel with 5% NH3-MeOH: CH2Cl2 to give 4-(1,2-diphenylethyl)-1H imidazole as a solid, (31 mg), AGN217242. 1H NMR (300 MHz, CD3OD): δ 7.38 (s, 1H), 7.10-7.26 (m, 8H), 7.08 (s, 1H), 4.41 (t, J=9 Hz, 3H), 3.43 (dd; J=9 Hz, 15 Hz, 1H), 3.27 (dd, J=6 Hz, 9 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customThe residue was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-02f87b0573134f6781f6138c17912e32
Source dataset
uspto-grants-2014_05
Patent number
US08735438B2

Reaction notes

Loading…