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

HRID 9387

Reaktionsgleichung

Reaktionsgleichung von HRID 9387
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]

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ab593658aea3483d87d1ad57cc97e475
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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