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

HRID 710479노트

반응식

HRID 710479 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9fc73a6621a145be8a326dbbeebf7b4a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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