4-(4-{2-[((2S)-3-{[8-(Benzyloxy)-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl]oxy}-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamide → 4-(4-[2-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamide

HRID 396046Notes

Reaction equation

HRID 396046 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:21][C@@H:22]([OH:51])[CH2:23][NH:24][CH2:25][CH2:26][C:27]2[CH:50]=[CH:49][C:30]([NH:31][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([NH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:39])[CH2:34][CH2:33]3)=[CH:29][CH:28]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:41]([NH:40][C:38]([N:35]1[CH2:36][CH2:37][CH:32]([NH:31][C:30]2[CH:49]=[CH:50][C:27]([CH2:26][CH2:25][NH:24][CH2:23][C@H:22]([OH:51])[CH2:21][O:20][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[C:18]4[C:13]=3[CH2:14][CH2:15][C:16](=[O:19])[NH:17]4)=[CH:28][CH:29]=2)[CH2:33][CH2:34]1)=[O:39])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 2

HCID 699857484-(4-{2-[((2S)-3-{[8-(Benzyloxy)-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl]oxy}-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 102325934-(4-[2-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamideYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-{2-[((2S)-3-{[8-(Benzyloxy)-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl]oxy}-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamide (0.16 g, 0.228 mmol) was dissolved in ethanol and 10% palladium on carbon (0.07 g) added. The solution was shaken in a Parr apparatus at 50 psi hydrogen atmosphere for 4 hours, filtered through a Celite pad and the solvent removed in vacuo. The residue was purified by flash silica gel chromatography on silica gel Merck-60 to yield the title compound (0.05 g, 0.082 mmol).

Workup

  1. filtrationfiltered through a Celite pad
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by flash silica gel chromatography on silica gel Merck-60

Sources & evidence

ORD record
ord-1f3a437c86124c3092220d399201c8d4
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

Loading…