8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine → (+/-)-(1S,5R,6R)-3-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azabicyclo[3.2.0]heptan-6-ol

HRID 2233002Notes

Reaction equation

HRID 2233002 reaction equation
[C@H:1]12[CH2:7][C@@H:6]([OH:8])[C@H:5]1[CH2:4][NH:3][CH2:2]2.[CH:9]([C:11]1[C:12]([F:23])=[CH:13][N:14]=[C:15]2[C:20]=1[N:19]=[C:18]([O:21][CH3:22])[CH:17]=[CH:16]2)=[CH2:10]>CCO>[F:23][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[CH2:9][CH2:10][N:3]1[CH2:4][C@H:5]3[C@H:1]([CH2:7][C@H:6]3[OH:8])[CH2:2]1)=[N:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2

Participants

4

Reactant 2

HCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 59295128(1S,5R,6R)-3-azabicyclo[3.2.0]heptan-6-ol

Product 1

HCID 59295127(+/-)-(1S,5R,6R)-3-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azabicyclo[3.2.0]heptan-6-olYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-(1S,5R,6R)-3-azabicyclo[3.2.0]heptan-6-ol (700 mg, 6.2 mmol) and 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (1.3 g, 6.2 mmol) in EtOH (4 mL) were heated at 85° C. After 12 h, the solution was concentrated and the residue purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (460 mg, 23%) as a yellow oil: LC/MS (ES) m/e 318 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-0e0acd44ae314da3b14722990934c327
Source dataset
uspto-grants-2010_05
Patent number
US07709472B2

Reaction notes

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