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Benzenamine, 4-fluoro-N-(1-methylethyl)- → 4-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde

HRID 717652
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HRID 717652 반응식
O[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[F:16][C:17]1[CH:26]=[CH:25][C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=1>C(Cl)Cl.CCN(CC)CC.C1(C)C=CC=CC=1>[F:16][C:17]1[CH:26]=[CH:25][C:20]([N:21]([CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=3)=[CH:5][CH:4]=2)[CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=1
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참가 물질

6

반응물 2

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-HCID 870750204-(5-(Hydroxymethyl)thiophen-2-yl)benzaldehyde

생성물 1

HCID 866606114-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde수율 20%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매
HCID 8471
Triethylamine
용매

실험 절차

To a stirred solution of the product of Step A (0.436 g, 2 mmol) in anhydrous CH2Cl2 (10 ml) and Et3N (0.3 ml) mesyl chloride (0.4 ml) was added at 0° C. and stirring was continued for 1 h. The solvents were evaporated to dryness under reduced pressure and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated and dried over MgSO4 and filtered. The filtrate was evaporated to give the crude product (0.63 g) as pale paste, which was taken up in anhydrous toluene and 4-fluoro-N-isopropylaniline (0.5 ml) was added to it. The mixture was stirred overnight at reflux and the solvent was evaporated. The residue was purified by FCC(SiO2, hexane/EtOAc) to give the title compound (0.14 g, 20%), as light creamy paste. 1H-NMR (CDCl3) 9.98 (s, 1H,); 7.82 (d, 2H, J=8.31 Hz); 7.66 (d, 2H, J=8.31 Hz); 7.28 (d, 1H, J=3.69 Hz); 6.93-6.86 (m, 3H); 6.81-6.76 (m, 2H); 4.79 (s, 2H); 4.08-3.99 (m, 1H); 1.22 (d, 6H, J=6.6 Hz).

후처리

  1. customThe solvents were evaporated to dryness under reduced pressure
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customto give the crude product (0.63 g) as pale paste, which
  9. stirringThe mixture was stirred overnight
  10. temperatureat reflux
  11. customthe solvent was evaporated
  12. customThe residue was purified by FCC(SiO2, hexane/EtOAc)

출처 및 근거

ORD 기록
ord-c37476af40484c118d72baef3dbd660e
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193716B2

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