HCID 178432569, compound → HCID 178432565, compound

HRID 49379Notes

Reaction equation

HRID 49379 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([CH3:25])[NH:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:25][C:22]1[NH:23][CH:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:15][CH:16]=2)[N:21]=1

Participants

4

Reactant 1

HCID 178432569HCID 178432569, compound

Product 1

HCID 178432565HCID 178432565, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a nitrogen-purged Parr flask, benzyl-{2-[4-(2-methyl-1H-imidazol-4-yl)-phenoxy]-ethyl}-carbamate (78 mg, 0.22 mmol) was dissolved in methanol (15 ml), and 10% Pd/C (20mg) was added in one portion. The material was then hydrogenated at about 45 psi for about four hours. The reaction mixture was then filtered through a pad of diatomaceous earth and the filter pad was washed with methanol. The filtrate was concentrated in vacuo, and the resulting material (49 mg, 100% yield) was carried on without further purification. LRMS ([M+H]+)=218.2.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-00dd19b2bdf64c6db7677df87b26e290
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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