Pyridine → (5-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-yl)carbamic acid phenyl ester

HRID 1433497노트

반응식

HRID 1433497 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:20][C:19]([NH2:21])=[CH:18][CH:17]=1.N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30].C(OCC)(=O)C>O1CCCC1.CN(C)C=O.O>[C:32]1([O:31][C:29](=[O:30])[NH:21][C:19]2[S:20][C:16]([S:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][CH:18]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 229363515-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamine

생성물 1

HCID 58930898(5-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-yl)carbamic acid phenyl ester수율 82%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

After dissolving 5-(6,7-dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamine (696 mg, 2.00 mmol) and pyridine (174 mg, 2.20 mmol) in a tetrahydrofuran (10 ml)-dimethylformamide (5 ml) mixed solvent, phenyl chloroformate (329 mg, 2.10 mmol) was added while cooling on ice, and the mixture was stirred at room temperature for 1 hour. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. After adding ethyl acetate and then hexane to the obtained crude product, the precipitated crystals were filtered out and blow-dried to obtain the title compound (720 mg, 1.64 mmol, 82%) as yellowish-brown crystals.

후처리

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe drying agent was filtered off
  6. distillationthe filtrate was distilled off under reduced pressure
  7. additionAfter adding ethyl acetate
  8. customhexane to the obtained crude product
  9. filtrationthe precipitated crystals were filtered out and
  10. customblow-dried

출처 및 근거

ORD 기록
ord-0487ae366d854945af6a4ab3647ca50c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612092B2

반응 노트

불러오는 중…