HCID 178439887, compound → HCID 178439888, compound

HRID 1450597Notes

Reaction equation

HRID 1450597 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-f7710f1e353f4ee58d8db924a0ef3580
Source dataset
uspto-grants-1997_02
Patent number
US05602127

Reaction notes

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