HCID 68196381, compound → HCID 68196382, compound

HRID 1626831Notes

Reaction equation

HRID 1626831 reaction equation
[CH2:1]([O:3][C:4](=[O:48])[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])=[C:39]([C:45]([CH3:47])=[CH2:46])[CH:38]=4)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])[CH3:2]>CO>[CH2:1]([O:3][C:4](=[O:48])[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:42]=[CH:41][C:40]([CH2:43][OH:44])=[C:39]([CH:45]([CH3:47])[CH3:46])[CH:38]=4)=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[N:10]=1)=[O:8])[CH3:2]

Participants

3

Reactant 1

HCID 68196381HCID 68196381, compound

Product 1

HCID 68196382HCID 68196382, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl({[5-(benzyloxy)-2-{(1-[4′-(hydroxymethyl)-3′-isopropenylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.094 g, 0.14 mmol) was dissolved in methanol (3 mL), and a palladium-activated carbon ethylenediamine complex (0.090 g) was added, followed by stirring at room temperature for 2 hours under a hydrogen atmosphere. The reaction solution was filtered with celite, the filtrate was concentrated under reduced pressure, and subsequently the resulting residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: dichloromethane/ethyl acetate) to afford the title compound (0.049 g, 0.088 mmol) as a yellowish white amorphous solid (yield 60%).

Workup

  1. additiona palladium-activated carbon ethylenediamine complex (0.090 g) was added
  2. filtrationThe reaction solution was filtered with celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customsubsequently the resulting residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-a34c3bc016c34792b0bc69fa73f2564a
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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