4-Toluenesulfonyl chloride → (11S)-3-bromo-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 549192노트

반응식

HRID 549192 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[N:14]4[C@@H:15]([CH3:19])[CH2:16][O:17][CH2:18][C:13]4=[N:12][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[NH4+:31].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[N:14]4[C@@H:15]([CH3:19])[CH2:16][O:17][CH2:18][C:13]4=[N:12][C:7]=3[C:8]([NH2:31])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67157683(11S)-3-bromo-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

생성물 1

HCID 58406168(11S)-3-bromo-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A 2-L, three-necked, Morton flask, equipped with mechanical stirrer, was charged with (11S)-3-bromo-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (9.12 g, 28.7 mmol) and CH2Cl2 (500 mL). The mixture was stirred at ambient temperature and MCPBA (10.35 g, 50% purity) was then added slowly in portions. The reaction was stirred at ambient temperature for 2 hours. Concentrated aqueous NH4OH solution (200 mL) was then slowly added to the reaction mixture followed by careful addition of p-toluenesulfonyl chloride (6.29 g, 33.0 mmol) in small portions. The reaction was stirred rapidly at ambient temperature overnight. The reaction was then treated with H2O (500 mL) and vigorous stirring was maintained for 2 hours. The layers were allowed to separate and a tan precipitate formed. The aqueous layer was removed and the organic layer, containing the precipitate, was filtered to give 6.0 g of (11S)-3-bromo-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid. The product was used in subsequent reactions without further purification.

후처리

  1. stirringThe reaction was stirred at ambient temperature for 2 hours
  2. stirringThe reaction was stirred rapidly at ambient temperature overnight
  3. stirringvigorous stirring
  4. temperaturewas maintained for 2 hours
  5. customto separate
  6. customa tan precipitate formed
  7. customThe aqueous layer was removed
  8. additionthe organic layer, containing the precipitate
  9. filtrationwas filtered

출처 및 근거

ORD 기록
ord-b335f0c948b44e3ca8236afe1453ee8c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943609B2

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