HCID 178439887, compound → HCID 178439888, compound

HRID 234031Notes

Reaction equation

HRID 234031 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:26]=[C:27]([C:31]3[NH:32][CH2:33][CH:34]([CH3:36])[N:35]=3)[CH:28]=[C:29]([CH3:30])[C:6]=2[N:5]=1)[CH2:2][CH3:3]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:26]=[C:27]([C:31]3[NH:32][CH:33]=[C:34]([CH3:36])[N:35]=3)[CH:28]=[C:29]([CH3:30])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 178439887HCID 178439887, compound

Product 1

HCID 178439888HCID 178439888, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 0.35 g (0.7 mMol) of methyl 4'-[[2-n-propyl-4-methyl-6-(4-methyl-imidazolin-2-yl)-1H-benzimidazol-1-yl]methyl]-biphenyl-2-carboxylate in 10 ml of toluene is mixed with 0.16 g palladium (10% on activated charcoal) under nitrogen and the mixture is refluxed for 66 hours. Then the toluene is evaporated off, the residue is taken up in methylene chloride, filtered and evaporated down. The crude product is chromatographed on silica gel (particle size: 0.032-0.063 mm) using as eluant methylene chloride to start with, later followed by methylene chloride/ethanol/ammonia (50:1:0.05, 20:1:0.02, 10:1:0.01 and 5:1:0.005). The uniform fractions are combined and evaporated down.

Workup

  1. temperaturethe mixture is refluxed for 66 hours
  2. customThen the toluene is evaporated off
  3. filtrationfiltered
  4. customevaporated down
  5. customThe crude product is chromatographed on silica gel (particle size: 0.032-0.063 mm)
  6. customevaporated down

Sources & evidence

ORD record
ord-aece89440deb44439f70b70f559bfd4e
Source dataset
uspto-grants-1997_01
Patent number
US05594003

Reaction notes

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