Triethylamine → HCID 86633733, compound

HRID 388614Notes

Reaction equation

HRID 388614 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1.CN(C=O)C>[Si:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([Cl:8])[C:18]=1[N+:19]([O-:21])=[O:20])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 28928tert-Butyldimethylsilyl chloride4×HCID 86633732HCID 86633732, compound

Product 1

HCID 86633733HCID 86633733, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent4×HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (83 mL, 0.60 mol) was added to a solution of 4-(2-chloro-3-nitroquinolin-4-ylamino)butan-1-ol (44.34 g, 149.9 mmol). A solution of tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) in DMF (60 mL) was slowly added, and the reaction was then stirred at room temperature of five hours. Additional tert-butyldimethylsilyl chloride (50 g of a 50% w/w solution in toluene) was added, and the reaction was stirred at room temperature for three days. Additional tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) was added, and the reaction was stirred at room temperature for three hours. Finally, additional triethylamine (83 mL, 0.60 mol) and tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) was added, and the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was filtered to remove a solid, and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform (250 mL), and the resulting solution was washed sequentially with 5% w/w aqueous ammonium chloride (3×150 mL), saturated aqueous sodium bicarbonate (2×150 mL), and brine (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was further dried under vacuum and passed through a layer of silica gel (eluting with dichloromethane) to provide 56.04 g of N-[4-(tert-butyldimethylsilanyloxy)butyl]-2-chloro-3-nitroquinolin-4-amine as a yellow solid.

Workup

  1. stirringthe reaction was stirred at room temperature for three days
  2. stirringthe reaction was stirred at room temperature for three hours
  3. stirringthe reaction was stirred at room temperature for 1.5 hours
  4. filtrationThe reaction mixture was filtered
  5. customto remove a solid
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in chloroform (250 mL)
  8. washthe resulting solution was washed sequentially with 5% w/w aqueous ammonium chloride (3×150 mL), saturated aqueous sodium bicarbonate (2×150 mL), and brine (150 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting solid was further dried under vacuum

Sources & evidence

ORD record
ord-1e19d51479e6498c85aaa818124b8c4b
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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