Methanol → HCID 18695437, 화합물

HRID 1870200노트

반응식

HRID 1870200 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[C:10]([C:18]#[N:19])=[CH:9][C:8]=1[N+:20]([O-])=O)[CH3:2].[CH2:24]1[CH2:28][O:27]CC1.C[OH:30]>[C].[Pd]>[C:18]([C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][C:11]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])[C:28](=[O:27])[C:24](=[O:30])[NH:20]2)#[N:19]

참가 물질

5

반응물 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 18695389HCID 18695389, 화합물

생성물 1

HCID 18695437HCID 18695437, 화합물수율 50%

시약·촉매·용매 1

HCID 178418390HCID 178418390, 화합물촉매

실험 절차

A mixture of 2.00 g of N-[4-cyano-5-(1H-imidazol-1-yl)-2-nitrophenyl]glycine ethyl ester, 40 ml of THF, 8 ml of methanol and 200 mg of 10% palladium-carbon was stirred under a hydrogen gas atmosphere to reduce the nitro group. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Then, 50 ml of chloroform and 4.43 ml of triethylamine were added to the resulting residue, followed by the dropwise addition of 1.69 ml of ethyl chloroglyoxylate under ice-cooling. After stirring at room temperature for 20 hours, the reaction mixture was diluted with chloroform. The diluted mixture was washed with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Then, 60 ml of ethanol and 0.5 ml of concentrated hydrochloric acid were added to the resulting residue, followed by heating under reflux for 3 hours. After cooling, the crystals so formed were collected by filtration and dried under reduced pressure to give 1.07 g (50%) of ethyl 2-[6-cyano-2,3-dioxo-7-(1H-imidazol-1-yl)-1,2,3,4-tetrahydroquinoxalin-1-yl]acetate.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThen, 50 ml of chloroform and 4.43 ml of triethylamine were added to the resulting residue
  4. additionfollowed by the dropwise addition of 1.69 ml of ethyl chloroglyoxylate under ice-
  5. temperaturecooling
  6. stirringAfter stirring at room temperature for 20 hours
  7. additionthe reaction mixture was diluted with chloroform
  8. washThe diluted mixture was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionThen, 60 ml of ethanol and 0.5 ml of concentrated hydrochloric acid were added to the resulting residue
  12. temperatureby heating
  13. temperatureunder reflux for 3 hours
  14. temperatureAfter cooling
  15. customthe crystals so formed
  16. filtrationwere collected by filtration
  17. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-2b610111f80940b99a3894cb3911ff9e
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06096743

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