Methane → Jtc-801

HRID 1070471

반응식

HRID 1070471 반응식
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=O.[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[N:11]=[C:10]([CH3:19])[CH:9]=1.[C:20](=[O:23])([O-])O.[Na+].[CH4:25].[CH2:26](O)[CH3:27]>N1C=CC=CC=1>[ClH:4].[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:20](=[O:23])[C:25]3[CH:16]=[CH:17][CH:8]=[CH:9][C:10]=3[CH2:19][O:5][C:1]3[CH:2]=[CH:15][C:14]([CH2:26][CH3:27])=[CH:13][CH:12]=3)[CH:16]=2)[N:11]=[C:10]([CH3:19])[CH:9]=1

참가 물질

7

반응물 5

HCID 297MethaneHCID 702EthanolHCID 65578Oxalyl chlorideHCID 2239952-Methylquinoline-4,6-diamineHCID 516892Sodium Bicarbonate

생성물 1

HCID 5311339Jtc-801수율 59%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 2-[(4-ethylphenoxy)methyl]benzoic acid (1.13 g, 4.4 mmol) obtained in Preparation Example 2-1 in chloroform (20 ml) was added oxalyl chloride (0.6 ml, 6.8 mmol) and the mixture was stirred at room temperature for 1 hr. Then the reaction mixture was concentrated under reduced pressure. To the obtained acid chloride were added pyridine (20 ml) and 4,6-diamino-2-methylquinoline (623 mg, 4 mmol) obtained in Preparation Example 1-1 and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was evaporated. The obtained crude product was dissolved in ethanol and treated with active charcoal, and the solvent was evaporated. The obtained residue was dissolved in ethyl acetate and 1N hydrochloric acid—ether solution was added. The resulting precipitate was collected by filtration. The obtained solid was heated and dried under reduced pressure to give the title compound (1.06 g, 59%, pale-yellow crystals).

후처리

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. customobtained in Preparation Example 1-1
  3. stirringthe mixture was stirred at room temperature for 10 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained crude product
  9. customthe solvent was evaporated
  10. dissolutionThe obtained residue was dissolved in ethyl acetate
  11. addition1N hydrochloric acid—ether solution was added
  12. filtrationThe resulting precipitate was collected by filtration
  13. temperatureThe obtained solid was heated
  14. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-b0cfc6de62284c53ac99652a5ad5619f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903094B2

연결된 노트

불러오는 중…