Benzylamine → 4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline

HRID 1108633Notes

Reaction equation

HRID 1108633 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24](Cl)[C:23]=2[N:22]=[CH:21]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>>[CH2:1]([NH:8][C:24]1[C:23]2[N:22]=[CH:21][N:20]([CH2:19][CH2:18][CH2:17][NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[C:32]=2[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 187839501-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

Product 1

HCID 187839524-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline

Conditions

Temperature
150 °C

Procedure

One ml of benzylamine was added to 30 mg (0.0831 mmol) of 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline and the mixture was stirred at 150° C. for 3 hours. Excess benzylamine was distilled off under reduced pressure and 1N hydrochloric acid and brine were added thereto. The mixture was extracted twice with methylene chloride. The organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=150:1 (v/v)) to obtain 35 mg (0.0811 mmol) of 4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline shown below as white powder (mp: 171-172.5° C.). ##STR39## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3330, 1700, 1590, 1540. 1H-NMR (CDCl3) δ (ppm) :1.46 (9H, s), 2.18 (2H, m), 3.25 (2H, m), 4.57 (2H, t, J=7.0 Hz), 4.64 (1H, br), 4.95 (2H, d, J=5.2 Hz), 6.05 (1H, br), 7.26~7.36 (4H, m), 7.47 (2H, d, J=7.6 Hz), 7.51 (1H, t, J=7.6 Hz), 7.82 (1H, s), 7.92 (2H, t, J=8.0 Hz).

Workup

  1. distillationExcess benzylamine was distilled off under reduced pressure and 1N hydrochloric acid and brine
  2. additionwere added
  3. extractionThe mixture was extracted twice with methylene chloride
  4. washThe organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution
  5. dry with materialdried (Na2SO4)
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=150:1 (v/v))

Sources & evidence

ORD record
ord-0e42850bd64a466ea83ea12f080fa30e
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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