4-{4-[2-({2-[3-(Aminocarbonyl)-4-(benzyloxy)phenyl]-2-hydroxyethyl}-amino)ethyl]anilino}-N-octyl-1-piperidinecarboxamide → 4-(4-{2-[2-(3-Carbamoyl-4-hydroxy-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid Octylamide

HRID 395983Notes

Reaction equation

HRID 395983 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:18]([OH:47])[CH2:19][NH:20][CH2:21][CH2:22][C:23]2[CH:46]=[CH:45][C:26]([NH:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:35])[CH2:30][CH2:29]3)=[CH:25][CH:24]=2)[CH:7]=[CH:8][C:9]=1[O:10]CC1C=CC=CC=1)=[O:3].[H][H]>C(O)C.[Pd]>[CH2:37]([NH:36][C:34]([N:31]1[CH2:32][CH2:33][CH:28]([NH:27][C:26]2[CH:45]=[CH:46][C:23]([CH2:22][CH2:21][NH:20][CH2:19][CH:18]([C:6]3[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([C:2](=[O:3])[NH2:1])[CH:5]=3)[OH:47])=[CH:24][CH:25]=2)[CH2:29][CH2:30]1)=[O:35])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 2

HCID 184256514-{4-[2-({2-[3-(Aminocarbonyl)-4-(benzyloxy)phenyl]-2-hydroxyethyl}-amino)ethyl]anilino}-N-octyl-1-piperidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 699856154-(4-{2-[2-(3-Carbamoyl-4-hydroxy-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid Octylamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-{4-[2-({2-[3-(Aminocarbonyl)-4-(benzyloxy)phenyl]-2-hydroxyethyl}-amino) ethyl]anilino}-N-octyl-1-piperidinecarboxamide was dissolved in ethanol (20 mL) and 10% palladium on carbon added (0.1 g). The mixture was shaken overnight on a Parr apparatus under 50 psi hydrogen, filtered through a Celite pad and the solvent removed in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol) to yield the title compound (0.030 g, 0.05 mmol)

Workup

  1. filtrationfiltered through a Celite pad
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol)

Sources & evidence

ORD record
ord-47d95aea7c734525aae7bd971b61ce6c
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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