Potassium Carbonate → Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 9490

반응식

HRID 9490 반응식
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[N+:42]([O-])=O)=[CH:25][CH:24]=1)([CH3:18])([CH3:17])[CH3:16]>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[NH2:42])=[CH:25][CH:24]=1)([CH3:18])([CH3:16])[CH3:17]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

생성물 1

HCID 21984367Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate수율 100.5%

시약·촉매·용매 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide촉매HCID 962Water용매3회HCID 6344Dichloromethane용매2회

실험 절차

Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55mL) were added sequentially to a solution of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 mL). The resulting biphasic mixture was stirred for 20 hours. The reaction was diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 8.5 g of tert-butyl{4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow-brown amorphous solid.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. washwashed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e14b4f690e7d423e92497dc07775b581
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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