HCID 86635363, compound → 4-{2-[(3S)-3-(Aminomethyl)-1-piperidinyl]ethyl}-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one

HRID 657128Notes

Reaction equation

HRID 657128 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][C@@H:17]([CH2:21][NH:22]C(=O)OCC4C=CC=CC=4)[CH2:16]3)[C:7]=2[N:33]=1>CO.[Pd].O=[Mn]=O>[NH2:22][CH2:21][C@@H:17]1[CH2:18][CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:8]2[C:9](=[O:12])[CH:10]=[N:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:33][C:7]2=3)[CH2:16]1

Participants

5

Reactant 1

HCID 86635363HCID 86635363, compound

Product 1

HCID 689911274-{2-[(3S)-3-(Aminomethyl)-1-piperidinyl]ethyl}-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl [((3S)-1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-3-piperidinyl)methyl]carbamate (0.37 g, 0.83 mmol) in MeOH (20 mL) was added 10% Pd/C (0.10 g). The solution was hydrogenated on a Parr apparatus at 50 PSI for 3 h. The Pd/C catalyst was filtered off, MnO2 (0.22 g, 2.48 mmol) was added, and the solution stirred at ambient temperature for 16 h. The MnO2 was filtered off and the crude material (yellowish oil) was used without further purification (0.26 g, 97% over 2 steps).

Workup

  1. filtrationThe Pd/C catalyst was filtered off
  2. filtrationThe MnO2 was filtered off
  3. customthe crude material (yellowish oil) was used without further purification (0.26 g, 97% over 2 steps)

Sources & evidence

ORD record
ord-4c832c8898ae4161905c57600b3a2079
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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