Hydrazine hydrate (1:1) → 1-(2-Aminoethyl)-4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-piperazinone

HRID 1787694Notes

Reaction equation

HRID 1787694 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2CC3C(=CC=CC=3)C2)[C:15](=[O:30])[CH2:14]1.O.NN>CCO>[NH2:21][CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][N:13]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=3)[N:9]=[CH:8][CH:7]=2)[CH2:14][C:15]1=[O:30]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866205952-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole

Product 1

HCID 575995921-(2-Aminoethyl)-4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-piperazinoneYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole-1,3(2H-dione (100 mg, 0.232 mmol) in EtOH (2 mL) was added hydrazine hydrate (120 μL, 3.85 mmol). After 2 h at 85° C., the solution was concentrated and the residue purified by column chromatography (silica, 5-10% MeOH in DCM (1% NH4OH)) yielding the title compound (46 mg, 66%) as a yellow oil: LCMS (ES) m/e 302 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue purified by column chromatography (silica, 5-10% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-9a4f0297f0af44dbb58c5d7903615c4b
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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