HCID 90421932, compound → 5-Methyl-7-pyridin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752615Notes

Reaction equation

HRID 1752615 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:5]2[C:15](=[O:31])[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=S)[C:4]2=[CH:3]1>[Ni].CCO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:5]2[C:15](=[O:31])[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH2:17][C:4]2=[CH:3]1

Participants

4

Reactant 1

HCID 90421932HCID 90421932, compound

Product 1

HCID 862958445-Methyl-7-pyridin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 28%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 5-methyl-7-pyridin-4-yl-2-(2-quinolin-2-yl-ethyl)-1,6-dioxo-5H-pyrrolo[3,4-c]pyridine-3-thione (40 mg, 0.09 mmol, see Example 11.1), Raney nickel (about 400 mg) in EtOH (12 ml) was stirred at r.t. under nitrogen for 3 hours. The Raney nickel was filtered off and the filtrate was concentrated and purified by preparative thin-layer chromatography (EA:MeOH=5:1) to give the title compound as a white solid (10 mg, 26%).

Workup

  1. filtrationThe Raney nickel was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by preparative thin-layer chromatography (EA:MeOH=5:1)

Sources & evidence

ORD record
ord-3a7ac2e9398d4227937052b5e200a30f
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

Loading…