Phenylmethyl [((3S)-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate → 1-{2-[(3S)-3-(Aminomethyl)-1-pyrrolidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

HRID 657036Notes

Reaction equation

HRID 657036 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:32])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][C@@H:17]([CH2:20][NH:21]C(=O)OCC3C=CC=CC=3)[CH2:16]2)=[N:5][CH:4]=1>CO.[Pd]>[NH2:21][CH2:20][C@@H:17]1[CH2:18][CH2:19][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[N:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:32])[CH2:16]1

Participants

4

Reactant 1

HCID 86635340Phenylmethyl [((3S)-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 688172201-{2-[(3S)-3-(Aminomethyl)-1-pyrrolidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl [((3S)-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (0.33 g, 0.761 mmol) in MeOH (30 mL) was added catalytic 10% Palladium on carbon (0.20 g) and the resulting solution was subjected to H2 at 50 PSI on a Parr shaker. The solution was filtered through a pad of Celite® and concentrated under reduced pressure to yield a colorless oil, (0.100 g, 43%).

Workup

  1. filtrationThe solution was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure
  3. customto yield a colorless oil, (0.100 g, 43%)

Sources & evidence

ORD record
ord-6aa6e405fa5f4bda99a12f4d18889e2e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…