HCID 68196361, compound → HCID 68196362, compound

HRID 1626783Notes

Reaction equation

HRID 1626783 reaction equation
[CH2:1]([O:3][C:4](=[O:45])[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]([CH2:43][OH: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:45])[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]([CH2:43][OH: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 68196361HCID 68196361, compound

Product 1

HCID 68196362HCID 68196362, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl({[5-(benzyloxy)-2-({1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.43 g, 0.71 mmol) was dissolved in a mixed solvent of ethyl acetate (20 mL) and dichloromethane (20 mL), and 10% palladium-activated carbon (0.080 g) was added, followed by stirring at room temperature for 2.5 hours under a hydrogen atmosphere. The reaction solution was filtered with celite, and the filtrate was concentrated under reduced pressure, whereby a solid was deposited. The resulting solid was collected by filtration, and dried under reduced pressure to afford the title compound (0.34 g, 0.66 mmol) as a white solid (yield 93%).

Workup

  1. additionwas added
  2. filtrationThe reaction solution was filtered with celite
  3. concentrationthe filtrate was concentrated under reduced pressure, whereby a solid
  4. filtrationThe resulting solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-221d9ca3e8ce4b71853f6f0ccdb94b4e
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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