HCID 70113859, compound → HCID 70114444, compound

HRID 868968Notes

Reaction equation

HRID 868968 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]1[N:25]=[C:16]2[CH:17]=[CH:18][C:19]3[C:24]([N:15]2[N:14]=1)=[CH:23][CH:22]=[CH:21][N:20]=3>[OH-].[Na+].CO.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]1[N:25]=[C:16]2[CH:17]=[CH:18][C:19]3[C:24]([N:15]2[N:14]=1)=[CH:23][CH:22]=[CH:21][N:20]=3

Participants

5

Reactant 1

HCID 70113859HCID 70113859, compound

Product 1

HCID 70114444HCID 70114444, compoundYield 46.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (E)-2-(2-(quinoxalin-2-yl)vinyl)-[1,2,4]triazolo[1,5-a][1,5]naphthyridine (32 mg, 0.099 mmol) in 1 N sodium hydroxide aqueous solution (1 mL) and methanol (2 mL) was added Pd/C (10%, 5 mg). The mixture was stirred under hydrogen at room temperature for 16 h. The mixture was filtered and the filtrate was concentrated, and purified by reverse phase prep-HPLC to give 15 mg of 2-(2-(quinoxalin-2-yl)ethyl)-[1,2,4]triazolo[1,5-a][1,5]naphthyridine as a yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by reverse phase prep-HPLC

Sources & evidence

ORD record
ord-f8089d7902f849fe8a09c4a6b4cf0d4c
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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