HCID 68106402, compound → HCID 70570910, compound

HRID 2403615Notes

Reaction equation

HRID 2403615 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30](C(OCC4C=CC=CC=4)=O)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C1COCC1.[Pd]>[CH3:13][N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 68106402HCID 68106402, compound

Product 1

HCID 70570910HCID 70570910, compoundYield 74.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-[3′-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)biphenyl-4-yl]piperazine-1-carboxylate (1.5 g) was dissolved in a mixed solution of MeOH (15 ml) and THF (15 ml). 10% Pd—C (150 mg) was added thereto, followed by stirring at room temperature for 1 day under a hydrogen atmosphere. The reaction mixture was filtered using Celite as a filtration assistant, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (2-{methyl [(4′-piperazin-1-ylbiphenyl-3-yl)methyl]amino}-2-oxoethyl)carbamate (860 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9483bd5ec7a4b1c8ac9cb303b5cdf6e
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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