HCID 57730432, compound → HCID 11528121, compound

HRID 2080324Notes

Reaction equation

HRID 2080324 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:13]=2)=[O:11])=[CH:4][C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][N:33]2[CH2:38][CH2:37][N:36](C(OCC3C=CC=CC=3)=O)[C@@H:35]([CH3:49])[CH2:34]2)[CH:27]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][N:33]3[CH2:38][CH2:37][NH:36][C@@H:35]([CH3:49])[CH2:34]3)[CH:27]=2)=[CH:4][C:5]([CH2:8][NH:9][C:10](=[O:11])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)[CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57730432HCID 57730432, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11528121HCID 11528121, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (2S)-4-[(2′-fluoro-5′-{[({3-[(1-methyl-4-piperidinyl)methyl]phenyl}carbonyl)amino]methyl)-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (120 mg, 0.18 mmol) in 5 mL of MeOH, was added 10% Pd/C (60 mg). The mixture was hydrogenated using a hydrogen balloon for 12 hours. After flittering off the catalyst, the mixture was concentrated and the residue was purified by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), to give the title compound (65 mg, 41%). LC/MS: m/z, 529 (M+H), 1.29 min.

Workup

  1. customfor 12 hours
  2. concentrationthe mixture was concentrated
  3. customthe residue was purified by Gilson reverse phase HPLC
  4. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)

Sources & evidence

ORD record
ord-8f09e0d0552b45a7b548ee30ee7517d7
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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