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

HRID 2192970

반응식

HRID 2192970 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d38906b3d654ce0b0404a14505580b1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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