Hydrazine → HCID 59295121, compound

HRID 2233004Notes

Reaction equation

HRID 2233004 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:14]1[CH2:20][C@H:19]3[C@H:16]([CH2:17][C@@H:18]3[N:21]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:15]1)=[N:9][C:8]([O:32][CH3:33])=[CH:7][CH:6]=2.NN>CCO>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:14]1[CH2:20][C@H:19]3[C@H:16]([CH2:17][C@@H:18]3[NH2:21])[CH2:15]1)=[N:9][C:8]([O:32][CH3:33])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59295124(+/-)-2-((1S,5R,6S)-3-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azabicyclo[3.2.0]hept-6-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59295121HCID 59295121, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (±)-2-((1S,5R,6S)-3-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azabicyclo[3.2.0]hept-6-yl)-1H-isoindole-1,3(2H)-dione (324 mg, 0.73 mmol) in EtOH (36 mL) was added NH2NH2 (0.34 mL, 10.9 mmol) dropwise. After 2 h at 85° C., the solution was concentrated and the residue purified via column chromatography (silica, 2-5% MeOH in DCM (1% NH4OH)) yielding the title compound (31 mg, 13%) as a yellow oil: LC/MS (ES) m/e 317 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-59a2289f1d2b472ba8e1cad8772e6e8f
Source dataset
uspto-grants-2010_05
Patent number
US07709472B2

Reaction notes

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