HCID 68196368, compound → HCID 52932119, compound

HRID 1626799Notes

Reaction equation

HRID 1626799 reaction equation
C([O:8][C:9]1[C:10]([C:38]([NH:40][CH2:41][C:42]([O:44]CC2C=CC=CC=2)=[O:43])=[O:39])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH:35]([OH:37])[CH3:36])=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[C:10]([C:38]([NH:40][CH2:41][C:42]([OH:44])=[O:43])=[O:39])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH:35]([OH:37])[CH3:36])=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15]

Participants

4

Reactant 1

HCID 68196368HCID 68196368, compound

Product 1

HCID 52932119HCID 52932119, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl [({5-(benzyloxy)-2-[(1-{4-[5-(1-hydroxyethyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetate (0.10 g, 0.16 mmol) was dissolved in ethyl acetate (30 mL), and 10% palladium-activated carbon (0.25 g) was added, followed by stirring at room temperature for 9 hours under a hydrogen atmosphere. After the reaction solution was filtered with celite, the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: ethyl acetate/methanol), and a fraction corresponding to the Rf value=0.10 (ethyl acetate/methanol=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.045 g, 0.089 mmol) as a yellow solid (yield 56%).

Workup

  1. filtrationAfter the reaction solution was filtered with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: ethyl acetate/methanol)
  4. concentrationa fraction corresponding to the Rf value=0.10 (ethyl acetate/methanol=4/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d47f4463e1014aa3ad3e9e3b48612314
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

Loading…