Benzophenone imine → HCID 57893435, compound

HRID 1821652Notes

Reaction equation

HRID 1821652 reaction equation
Cl[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)=[CH:14][N:15]=[C:10]3[NH:9][C:8]2=[O:28])=[CH:4][CH:3]=1.[C:31](=[NH:44])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:31](=[N:44][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)=[CH:14][N:15]=[C:10]3[NH:9][C:8]2=[O:28])=[CH:4][CH:3]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 136809Benzophenone imineHCID 11553670HCID 11553670, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57893435HCID 57893435, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 1-(4-chlorobenzyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydro-imidazo[4,5-b]pyrazin-2-one (19 mg, 0.04 mmol; Example 28), benzhydrylideneamine (16 mg, 0.08 mmol), Pd2(dba)3(7 mg, 0.007 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl0bis[diphenylphosphine] also known as XantPhos (13 mg, 0.027 mmol) in toluene (0.5 mL) was added sodium tert-butoxide (10 mg; 0.1 mmol) and the resultant mixture was heated to 95° C. overnight. After cooling to room temperature, the reaction was diluted with water and extracted with EtOAc. Concentration of the organic phase under reduced pressure afforded a crude residue, which was purified by silica gel chromatography [EtOAc/hexane (3:2)] to afford 1-[4-(benzhydrylidene-amino)benzyl]-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one (14 mg) as a yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. customConcentration of the organic phase under reduced pressure afforded a crude residue, which
  3. customwas purified by silica gel chromatography [EtOAc/hexane (3:2)]

Sources & evidence

ORD record
ord-160d0f5f38ab4f138b2903431adcd91c
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

Loading…