Triethylamine → 7-(Methyloxy)-1-(2-oxiranylmethyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one
Reaction equation
O[CH:2]([CH2:17][OH:18])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[N:12]=2)[CH2:7][CH2:6][C:5]1=[O:16].C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[CH3:15][O:14][C:11]1[N:12]=[C:13]2[C:8]([CH2:7][CH2:6][C:5](=[O:16])[N:4]2[CH2:3][CH:2]2[CH2:17][O:18]2)=[CH:9][CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(2,3-dihydroxypropyl)-7-(methyloxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (2.325 g, 9.226 mmol) in DCM (40 ml) and triethylamine (1.915 ml, 13.839 mmol) at 0° C. under argon was treated with methanesulfonyl chloride (0.714 ml, 9.226 mmol) and stirred at 0° C. for 0.5 h. The reaction mixture was then treated with water (100 ml), extracted with DCM (3×100 ml). The organic extracts were dried (MgSO4), and evaporated. The residue was then dissolved in methanol (50 ml) and treated with potassium carbonate (6.366 g, 46.130 mmol) and stirred at rt for 15 min. The reaction mixture was then treated with water (100 ml), extracted with DCM (3×200 ml). The organic extracts were dried (MgSO4), evaporated and chromatographed (0-100% ethyl acetate:Hexane) to give the product as a yellow oil (428 mg, 20%).
Workup
- extractionextracted with DCM (3×100 ml)
- dry with materialThe organic extracts were dried (MgSO4)
- customevaporated
- dissolutionThe residue was then dissolved in methanol (50 ml)
- stirringstirred at rt for 15 min
- extractionextracted with DCM (3×200 ml)
- dry with materialThe organic extracts were dried (MgSO4)
- customevaporated
- customchromatographed (0-100% ethyl acetate:Hexane)
Sources & evidence
- ORD record
- ord-015fe4849b4b4af79d450dedca752f11
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389524B2
Reaction notes
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