6-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate → 2-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 2356339Notes

Reaction equation

HRID 2356339 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.[O:21]=[C:22]1[CH2:27][NH:26][CH2:25][CH2:24][N:23]1[CH2:28][CH2:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40]>CCO>[CH3:18][O:17][C:14]1[N:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[N:26]1[CH2:25][CH2:24][N:23]([CH2:28][CH2:29][N:30]2[C:31](=[O:40])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]2=[O:39])[C:22](=[O:21])[CH2:27]1

Participants

4

Reactant 2

HCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonateHCID 684533342-[2-(2-oxo-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 684555142-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole-1,3(2H)-dioneYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (169 mg, 0.55 mmol) and 2-[2-(2-oxo-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione (150 mg, 0.55 mmol) in EtOH (2 mL) were stirred at 85° C. After 12 h, the solution was concentrated and the residue purified via column chromatography (silica, 0-8% MeOH in DCM (1% NH4OH)) yielding the title compound (100 mg, 42%) as a light yellow solid: LCMS (ES) m/e 432 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue purified via column chromatography (silica, 0-8% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-a59c4c7876e24c65993fb6d2d9e21404
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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