Ethyl Acetate → 1-Butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate

HRID 2192970

Reaction equation

HRID 2192970 reaction equation
[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:20]=[N:19][CH:18]=[CH:17][C:9]=1[C:10]([OH:16])=[N:11]2)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].C1(N[S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])C=CC=CC=1.C(OCC)(=O)C>CC(N(C)C)=O>[F:38][C:37]([F:40])([F:39])[S:34]([O:16][C:10]1[C:9]2[CH:17]=[CH:18][N:19]=[CH:20][C:8]=2[C:7]2[C:12](=[CH:13][CH:14]=[N:15][C:6]=2[O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:11]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 178450362HCID 178450362, compound

Product 1

HCID 593754901-Butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-ol (2 g, 7.43 mmol) and cesium carbonate (4.84 g, 14.85 mmol) in DMA (75 ml), N-phenyltrifluoromethanesulfonamide (5.31 g, 14.85 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 7 min. The reaction was then cooled to room temperature and added to ethyl acetate. The organic mixture was washed with aqueous sodium hydrogen carbonate (saturated), aqueous sodium carbonate (saturated), and brine. The organic extracts were combined, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes, to afford 1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 10.68 (s, 1H), 9.08 (d, 1H), 8.52 (d, 1H), 8.14 (d, 1H), 7.62 (d, 1H), 4.70 (t, 2H), 1.96 (m, 2H), 1.57 (m, 2H), 1.00 (t, 3H). LRMS (APCI) calc'd for (C16H15F3N3O4S) [M+H]+, 402.1; found 402.0.

Workup

  1. additionwas added
  2. temperatureThe reaction was then cooled to room temperature
  3. washThe organic mixture was washed with aqueous sodium hydrogen carbonate (saturated), aqueous sodium carbonate (saturated), and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3d38906b3d654ce0b0404a14505580b1
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Linked notes

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