HCID 68775359, compound → HCID 68775158, compound

HRID 1711193Notes

Reaction equation

HRID 1711193 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C@H:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][N:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N+:35]([O-])=O)[C:19]2=[O:38])[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:13][CH2:14][CH:15]([N:18]2[C@H:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:21][N:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[NH2:35])[C:19]2=[O:38])[CH2:16][CH2:17]1)[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68775359HCID 68775359, compound

Product 1

HCID 68775158HCID 68775158, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3-{4-[(R)-3-(2-nitro-phenyl)-2-oxo-5-phenyl-imidazolidin-1-yl]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (180 mg, 0.334 mmol) in CH3OH (3 ml) was added Pd/C (20 mg, 50%). The mixture was hydrogenated under H2 (2 atm.) for 10 min. Filtration and concentration gave (3-{4-[(R)-3-(2-amino-phenyl)-2-oxo-5-phenyl-imidazolidin-1-yl]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (160 mg, 94%). Treatment with TFA (1 ml) and CH2Cl2 (1 ml) according to general procedure C gave (R)-3-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-1-(2-amino-phenyl)-4-phenyl-imidazolidin-2-one (114 mg, 94%).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-acf151cbc5444e8fb26a99b896581955
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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