Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate → 3-Amino-1-benzyl-6-phenyl-3,4-dihydro-1,7-naphthyridin-2(1H)-one

HRID 2221099Notes

Reaction equation

HRID 2221099 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][CH:16]=2)[CH2:11][CH:10]([NH:24]C(=O)OCC2C=CC=CC=2)[C:9]1=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CO.[Pd]>[NH2:24][CH:10]1[CH2:11][C:12]2[C:17](=[CH:16][N:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]1=[O:35]

Participants

5

Reactant 1

HCID 11605071Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate

Product 1

HCID 586715523-Amino-1-benzyl-6-phenyl-3,4-dihydro-1,7-naphthyridin-2(1H)-oneYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3G (300 mg, 0.65 mmol) in THF (80 mL) and MeOH (80 niL) at RT was added palladium 5% wt. on activated carbon (150 mg). The reaction mixture was stirred under a hydrogen balloon for lh. The reaction was filtered and the filtrate concentrated to give the title compound as a foam (144 mg, 91%). LC/MS (method A): retention time=2.37 min, (M+H)+=330.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-aeff6fa0e5ba453bad629049543c686f
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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