Dimethylformamide → HCID 25123070, compound

HRID 2382159Notes

Reaction equation

HRID 2382159 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl-].[N:13]1[C:22]2[C:17](=[CH:18][N:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[CH3:23]N(C=O)C>CCOC(C)=O.O>[CH3:23][C:18]1[N:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[CH:16]=[CH:15][C:14]([O:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[N:13]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 86641724HCID 86641724, compound

Product 1

HCID 25123070HCID 25123070, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Piperidin-1-ylethanol (43 mg, 0.34 mmol) was treated with a 60% dispersion of NaH in mineral oil (17 mg, 0.42 mmol) in 2 mL of DMF. The mixture was stirred for 20 minutes and the 1,6-naphthyridine chloride was added, and the solution was stirred at 50° C. for 16 hours. The solution was cooled to room temperature and diluted with EtOAc and H2O. The organic layer was separated and washed with saturated aqueous sodium bicarbonate solution (NaHCO3) and brine, and dried over magnesium sulfate. The organics were filtered, concentrated, and purified by silica gel chromatography eluting with a gradient of dichloromethane/MeOH/NH4OH to yield 33 mg (41%) of compound 16. LCMS (EI) m/z 274 (M+1).

Workup

  1. stirringthe solution was stirred at 50° C. for 16 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium bicarbonate solution (NaHCO3) and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe organics were filtered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography
  8. washeluting with a gradient of dichloromethane/MeOH/NH4OH

Sources & evidence

ORD record
ord-92bdce71854b4cef8d87407d0c9d6294
Source dataset
uspto-grants-2012_09
Patent number
US08258301B2

Reaction notes

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