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

HRID 1818137

Reaction equation

HRID 1818137 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[C:21]([N+:26]([O-])=O)[CH:22]=[N:23]2)=[CH:18][CH:17]=1>O.ClCCl.[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1)C>[NH2:26][C:21]1[CH:22]=[N:23][C:24]2[C:19]([C:20]=1[NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[CH:18][CH:17]=[C:16]([Br:15])[CH:25]=2

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-65d0a8f437a94602bcd55d4940fad567
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Linked notes

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