HCID 86295427, compound → HCID 90421727, compound

HRID 1752610Notes

Reaction equation

HRID 1752610 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:5]2[C:16](=[O:32])[N:17]([CH2:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[C:18](=[O:19])[C:4]2=[CH:3]1>C(O)(=O)C.[Zn]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[C:5]2[CH:16]([OH:32])[N:17]([CH2:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[C:18](=[O:19])[C:4]2=[CH:3]1

Participants

4

Reactant 1

HCID 86295427HCID 86295427, compound

Product 1

HCID 90421727HCID 90421727, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

Zinc (0.38 g, 5.8 mmol) was added rapidly to a solution of 5-methyl-7-(4-methyl-piperazin-1-yl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (1 g, 2.318 mmol, see Example 2) in acetic acid (30 ml). The reaction was heated at about 110° C. for about 4 h. The solvent was removed. The residue was purified on a silica column (DCM/MeOH=10:1) to afford the title compound (0.5 g, 49.8% yield).

Workup

  1. customThe solvent was removed
  2. customThe residue was purified on a silica column (DCM/MeOH=10:1)

Sources & evidence

ORD record
ord-89bd5af2e22c4ce793c0defe354eba8b
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

Loading…