1,1'-Carbonyldiimidazole → HCID 178488769, compound

HRID 452105Notes

Reaction equation

HRID 452105 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:14]=1[CH:15]=O.[Si](C#N)(C)(C)C.[N:29]1([C:34](N2C=CN=C2)=[O:35])C=CN=[CH:30]1>[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:15]([C:14]4[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:13]=4[O:12][CH3:11])[CH2:30][NH:29][C:34]3=[O:35])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 691752,4-DimethoxybenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 178507353HCID 178507353, compound

Product 1

HCID 178488769HCID 178488769, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound was synthesized starting from 1H-benzo[d]imidazol-5-amine (0.400 g, 3 mmol), 2,4-dimethoxybenzaldehyde (0.5 g, 3 mmol), TMSCN (0.375 mL, 3 mmol), Pd/C (10%, 0.02 g), TEA 1.05 mL, 7.5 mmol), di-(imidazol-1-yl)methanone (0.730 g, 4.5 mmol) as described in method 2 to give 1-(1H-benzo[d]imidazol-5-yl)-5-(2,4-dimethoxyphenyl)imidazolidin-2-one (yield: 0.305 g, 0.9 mmol, 30%). Treating with borontribromide (0.512 mL, 5.41 mmol) as described for Example 151 gives the title compound.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-03509728bcf94581b05f204521517a57
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

Loading…