Tetrahydrofuran → 5-(4-Propylphenyl)-3-(1,2,3,4-tetrahydroquinolin-5-yl)-1,2,4-oxadiazole

HRID 710479ノート

反応式

HRID 710479 の反応式
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][CH:19]=[N:20]4)[N:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C1COCC1>CC(O)=O>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH2:17][CH2:18][CH2:19][NH:20]4)[N:11]=2)=[CH:8][CH:9]=1)[CH2:2][CH3:3]

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 667269365-(4-Propylphenyl)-3-(quinolin-5-yl)-1,2,4-oxadiazole

生成物 1

HCID 667263485-(4-Propylphenyl)-3-(1,2,3,4-tetrahydroquinolin-5-yl)-1,2,4-oxadiazole収率 48.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of the product of Step C (0.069 g; 0.219 mmol) in AcOH (1 ml) and anhydrous THF (1.5 ml) NaBH3CN (3×0.07 g; 3.34 mmol) was added portion wise over a period of 2 h, while the temperature of the reaction mixture was kept <15° C. The solvents were removed in vacuo and the residue was diluted to 15 ml with EtOAc, washed with 5% NaOH, H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was dissolved in a mixture of CF3CO2H and EtOH (2 ml+2 ml), refluxed for 1 h and re evaporated. The residue was treated with NH4OH saturated CH2Cl2 (5 ml) and evaporated under reduced pressure. The residue was purified by FCC (SiO2, CH2Cl2) to give the title compound (0.034 g; 48%), as colourless solid. 1H-NMR (CDCl3) 0.95 (tr, 3H, J=7.4 Hz); 1.61-1.75 (m, 2H); 1.91-2.0 (m, 2H); 2.66 (tr, 2H, J=7.8 Hz); 3.09 (tr, 2H, J=6.5 Hz); 3.29-3.33 (m, 2H); 3.8 (broad s, 1H); 6.6 (dd, 1H, J=1, 8 Hz); 7.07 (tr, 1H, J=7.9 Hz); 7.3-7.35 (m, 3H); 8.1 (d, 2H, J=8.3 Hz).

後処理

  1. customwas kept <15° C
  2. customThe solvents were removed in vacuo
  3. additionthe residue was diluted to 15 ml with EtOAc
  4. washwashed with 5% NaOH, H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness under reduced pressure
  8. dissolutionThe residue was dissolved in a mixture of CF3CO2H and EtOH (2 ml+2 ml)
  9. temperaturerefluxed for 1 h
  10. customre evaporated
  11. additionThe residue was treated with NH4OH saturated CH2Cl2 (5 ml)
  12. customevaporated under reduced pressure
  13. customThe residue was purified by FCC (SiO2, CH2Cl2)

出典と根拠

ORDレコード
ord-9fc73a6621a145be8a326dbbeebf7b4a
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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