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

HRID 9387

반응식

HRID 9387 반응식
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([Br:37])=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[N+:38]([O-])=O)([CH3:18])([CH3:17])[CH3:16]>O.ClCCl.[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1)C>[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([Br:37])=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[NH2:38])([CH3:18])([CH3:16])[CH3:17]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984414Tert-butyl [4-(7-bromo-3-nitroquinolin-4-ylamino)butyl]carbamate

생성물 1

HCID 21984174Tert-butyl [4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate수율 99%

시약·촉매·용매 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide촉매HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of sodium hydrosulfite (43.35 g, 249 mmol) and potassium carbonate (38.28 g, 277 mmol) in water (300 mL) was added to a mixture of tert-butyl[4-(7-bromo-3-nitroquinolin-4-ylamino)butyl]carbamate (24.3 g, 55.3 mmol) and 1,1′-diethyl-4,4′-bipyridinium dibromide (1.03 g, 2.76 mmol) in dichloromethane (368 mL) and water (40 mL), and the reaction was stirred overnight at ambient temperature. The reaction mixture was filtered through a layer of CELITE filter aid. The aqueous filtrate was extracted with dichloromethane, and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 22.4 g of tert-butyl[4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate as a brown powder.

후처리

  1. filtrationThe reaction mixture was filtered through a layer of CELITE
  2. filtrationfilter aid
  3. extractionThe aqueous filtrate was extracted with dichloromethane
  4. dry with materialthe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ab593658aea3483d87d1ad57cc97e475
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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