HCID 20255153, compound → HCID 20255146, compound

HRID 638028Notes

Reaction equation

HRID 638028 reaction equation
C([N:8]([CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40](=[O:42])[NH2:41])[CH:34]=1)[CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([CH3:28])[C:21]([CH3:27])=[C:22]([C:24](=[O:26])[CH3:25])[N:23]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:40]([C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][C:36]=1[OH:39])[O:32][CH2:31][CH2:30][NH:8][CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([CH3:28])[C:21]([CH3:27])=[C:22]([C:24](=[O:26])[CH3:25])[N:23]=2)=[CH:15][CH:14]=1)(=[O:42])[NH2:41]

Participants

5

Reactant 2

HCID 20255153HCID 20255153, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20255146HCID 20255146, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 13.2 g of crude 1-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[4-(4-acetyl-1,5-dimethyl-1H-imidazol-2-yl)-phenoxy]-2-propanol in 140 ml of methanol is hydrogenated with the addition of 1.3 g of palladium-on-carbon catalyst until 1 molar equivalent of hydrogen has been absorbed. After filtration and evaporation of the solvent, an oil is obtained which, after recrystallising twice from ethanol, yields 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(4-acetyl-1,5-dimethyl-1H-imidazol-2-yl)-phenoxy]-2-propanol having a melting point of 128°-130°.

Workup

  1. customhas been absorbed
  2. filtrationAfter filtration and evaporation of the solvent
  3. customan oil is obtained which
  4. customafter recrystallising twice from ethanol

Sources & evidence

ORD record
ord-44e3ab0574c94780b0bedcc58ae1cd73
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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