huagongshe.com
HRID245217

反应详情

EQUATION

反应方程式

HRID 245217 的结构方程式

REACTANTS

反应物

2
结构：C1CC(N2CCOCC2)CCN1
HCID795724

4-Morpholinopiperidine

C9H18N2O

结构：CCOc1cc2nc(-c3cccc(C(F)(F)F)c3)c(CBr)c(C(=O)OC)c2cc1S(=O)(=O)CC
HCID67383752

未命名化合物

PRODUCTS

生成物

1
结构：CCOc1cc2nc(-c3cccc(C(F)(F)F)c3)c(CN3CCC(N4CCOCC4)CC3)c(C(=O)OC)c2cc1S(=O)(=O)CC
HCID67418349

未命名化合物

收率 51%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

A suspension of methyl 3-(bromomethyl)-7-(ethyloxy)-6-(ethylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.54 g, 6.31 mmol) and 4-(4-piperidinyl)morpholine (1.397 g, 8.20 mmol) in acetonitrile (30 mL) was stirred for 3 h. The solvent was removed under reduced pressure, and the residue was diluted with NaHCO3 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in DMF and purified via HPLC (Biotage RP, 0-50% MeCN/H2O with 0.1% TFA). The fractions containing the product were neutralized with saturated aqueous NaHCO3 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to afford methyl 7-(ethyloxy)-6-(ethylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.09 g, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ8.37 (s, 1H), 7.97 (s, 1H), 7.90 (t, J=8.53 Hz, 2H), 7.76-7.81 (m, 2H), 4.39 (q, J=6.94 Hz, 2H), 4.01 (s, 3H), 3.50-3.64 (m, 9H), 2.63 (d, J=11.29 Hz, 2H), 2.38 (br. s., 4H), 1.95-2.05 (m, 1H), 1.81 (t, J=11.17 Hz, 2H), 1.61 (d, J=11.54 Hz, 2H), 1.45 (t, J=7.03 Hz, 3H), 1.19-1.30 (m, 2H), 1.15 (t, J=7.40 Hz, 3H); MS (m/z) 650.2 (M+H+).

WORKUP

后处理

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with NaHCO3
  3. extractionextracted with methylene chloride (three times)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in DMF
  9. custompurified via HPLC (Biotage RP, 0-50% MeCN/H2O with 0.1% TFA)
  10. additionThe fractions containing the product
  11. extractionextracted with methylene chloride (three times)
  12. washThe combined organic extracts were washed with brine
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated