HCID 18783946, compound → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

HRID 1108641Notes

Reaction equation

HRID 1108641 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16](Cl)[C:15]=1[N+:25]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[NH2:25][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

4

Reactant 1

HCID 18783946HCID 18783946, compound

Product 1

HCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamateYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

38.69 mg (97.98 mmol) of 4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline was dissolved in 900 ml of methanol. 10 g of 10% palladium-carbon was added thereto and the mixture was stirred for 2 days under hydrogen atmosphere. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure. A sodium hydrogencarbonate aqueous solution was added to the residue and the solution was extracted twice with chloroform. The organic phase was washed with brine and dried (Na2SO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 (v/v)) to obtain 21.37 mg (64.67 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino] quinoline shown below as a green brown amorphous substance. ##STR50## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm): 1.44 (9H, s), 1.64 (4H, m), 3.16 (2H, m), 3.26 (2H, t, J=6.8 Hz), 3.8 (2H, br) 4.6 (1H, br), 7.45 (2H, m), 7.82 (1H, m), 7.97 (1H, m), 8.47 (1H, s).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA sodium hydrogencarbonate aqueous solution was added to the residue
  4. extractionthe solution was extracted twice with chloroform
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 (v/v))

Sources & evidence

ORD record
ord-2a6ded92e98342b3b670ed3e17835707
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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