HCID 68196363, compound → HCID 68196364, compound

HRID 1626786Notes

Reaction equation

HRID 1626786 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[CH2:5][NH:6][C:7]([C:9]1[C:14]([O:15]CC2C=CC=CC=2)=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][C:40]([C:43](=[O:45])[CH3:44])=[CH:39][CH:38]=4)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])[CH3:2]>C(OCC)(=O)C.ClCCl.[Pd]>[CH2:1]([O:3][C:4](=[O:46])[CH2:5][NH:6][C:7]([C:9]1[C:14]([OH:15])=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:32]=[CH:33][C:34]([C:37]4[CH:38]=[CH:39][C:40]([CH:43]([OH:45])[CH3:44])=[CH:41][CH:42]=4)=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[N:10]=1)=[O:8])[CH3:2]

Participants

5

Reactant 1

HCID 68196363HCID 68196363, compound

Product 1

HCID 68196364HCID 68196364, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl({[2-{[1-(4′-acetylbiphenyl-4-yl)piperidin-4-yl]methyl}-5-(benzyloxy)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.67 g, 1.1 mmol) was dissolved in a mixed solvent of ethyl acetate (35 mL) and dichloromethane (35 mL), and 10% palladium-activated carbon (0.65 g) was added, followed by stirring at room temperature for 8 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: dichloromethane/ethyl acetate), and a fraction corresponding to the Rf value=0.27 (dichloromethane/ethyl acetate=1/3) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.44 g, 0.82 mmol) as a white solid (yield 77%).

Workup

  1. additionwas added
  2. filtrationAfter the reaction solution was filtered with celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.27 (dichloromethane/ethyl acetate=1/3) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d051ad65d236472e80cfc94e076eaac5
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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