Ammonia → HCID 18783984, compound

HRID 1108650Notes

Reaction equation

HRID 1108650 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-])=[CH:17][C:16]=2[N:15]=[C:14]1[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:28].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:28])[C:16]=2[N:15]=[C:14]1[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 73974-Toluenesulfonyl chlorideHCID 18783977HCID 18783977, compound

Product 1

HCID 18783984HCID 18783984, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

0.124 g (0.335 mmol) of 1-[4-(tert-Butoxycarbonylamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinoline-5-oxide was dissolved in 3 ml of methylene chloride. Two ml of concentrated aqueous ammonia (29%) and a solution of 70 mg (0.368 mg) of p-toluenesulfonyl chloride in 1 ml of methylene chloride were added thereto under ice-cooling and the mixture was stirred for 30 minutes, then stirred at room temperature for 3 hours. After brine was added, the reaction mixture was extracted with chloroform and dried (Na2SO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=30:1 to 20:1 (v/v)) to obtain 0.114 g (0.309 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinoline-4-amine shown below as a pale brown solid. ##STR60## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3460, 3370, 3100, 1710, 1640, 1540, 1380, 1260, 1170, 750.

Workup

  1. temperatureunder ice-cooling
  2. stirringstirred at room temperature for 3 hours
  3. extractionthe reaction mixture was extracted with chloroform
  4. dry with materialdried (Na2SO4)
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1 to 20:1 (v/v))

Sources & evidence

ORD record
ord-bcee5df6e6e04025836a66a23b61f071
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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