(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-one → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one

HRID 2374788Notes

Reaction equation

HRID 2374788 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:4][CH:3]=1.[C:27]([Cu])#[N:28]>CN(C=O)C>[C:27]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:25][CH:26]=1)#[N:28]

Participants

4

Reactant 2

HCID 9911635(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 59923742(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-oneYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

(R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a]-imidazol-2-one (13.5 g, 29.9 mmol) was dissolved in anhydrous DMF (70 mL) and CuCN (3.22 g, 35.9 mmol) was added. The reaction mixture was heated to 140° C. under argon for 40 h. When the reaction was complete, the solvent was removed under reduced pressure and the residue was diluted with CH2Cl2. The organic solution was washed four times alternately with 5% aqueous pyridine then water. The organic layer was dried over Na2SO4 and filtered through a diatomaceous earth pad. The filtrate was concentrated and purified by silica gel column chromatography using a mixture of CH2Cl2-hexane (10:1) as an eluent to afford 9.19 g of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a]-imidazol-2-one.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CH2Cl2
  3. washThe organic solution was washed four times alternately with 5% aqueous pyridine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered through a diatomaceous earth pad
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. additiona mixture of CH2Cl2-hexane (10:1) as an eluent

Sources & evidence

ORD record
ord-f01a2334b2b14a1880daa6a696f4794a
Source dataset
uspto-grants-2008_12
Patent number
US07462637B2

Reaction notes

Loading…