Benzylamine → HCID 18783936, compound

HRID 1108639Notes

Reaction equation

HRID 1108639 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][CH2:20][N:21]1[C:33]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[C:25](Cl)[C:24]=2[N:23]=[CH:22]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>>[CH2:1]([NH:8][C:25]1[C:24]2[N:23]=[CH:22][N:21]([CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[C:33]=2[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 18783939HCID 18783939, compound

Product 1

HCID 18783936HCID 18783936, compound

Conditions

Temperature
150 °C

Procedure

2 ml of benzylamine was added to 70 mg (0.187 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-4-chloro-1H-imidazo-[4,5-c]quinoline. The resulting mixture was heated at 150° C. and stirred for 3 hours. An excess amount of benzylamine was distilled off under reduced pressure and 1N hydrochloric acid and brine were added thereto. The resulting solution was extracted twice with methylene chloride. The organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution and dried (Na2SO4). The solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=150:1 (v/v)) to obtain 79 mg (0.177 mmol) of 4-benzylamino-1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline shown below as white powder (mp: 151 to 153.5° C.). ##STR46## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3380, 3310, 2930, 1680, 1595, 1540, 1245, 1160.

Workup

  1. distillationAn excess amount of benzylamine was distilled off under reduced pressure and 1N hydrochloric acid and brine
  2. additionwere added
  3. extractionThe resulting solution 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 then 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-8531154080ab49deb39533ee170dc0be
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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