4-Toluenesulfonyl chloride → HCID 22254506, compound

HRID 434003Notes

Reaction equation

HRID 434003 reaction equation
[O:1]([CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[NH2:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=O)[CH2:23][CH:24]([CH3:26])[CH3:25].[OH-].[NH4+:30].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH2:23]([C:22]1[N:10]([CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:30])[C:12]=2[N:21]=1)[CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66054Isovaleryl chlorideHCID 12114241HCID 12114241, compound

Product 1

HCID 22254506HCID 22254506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N4-(2-Phenoxyethyl)quinoline-3,4-diamine (1.5 g, 5.4 mmol) and isovaleryl chloride (0.8 ml, 6.4 mmol) were combined and treated according to the general procedures of Parts C-E of Example 129. The resulting product, 2-isobutyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline-5N-oxide (1.6 g, 4.5 mmol) was dissolved in dichloromethane (200 ml) and ammonium hydroxide (50 ml) was added. The reaction was chilled (ice bath) and p-toluenesulfonyl chloride (0.85 g, 4.5 mmol) was slowly added over a period of 20 minutes. The cooling bath was removed and the reaction was maintained at ambient temperature overnight. The phases were separated and the organic phase was sequentially washed with I% aqueous sodium carbonate (3×), water, brine; dried (Na2SO4); and concentrated to near dryness in vacuo. Hexane was added to provide a precipitate. The solid was collected and purified by recrystallization from acetonitrile to yield 0.96 g of 2-isobutyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, m.p. 176.6-177.8° C.

Workup

  1. additiontreated
  2. additionwas slowly added over a period of 20 minutes
  3. customThe cooling bath was removed
  4. customThe phases were separated
  5. washthe organic phase was sequentially washed with I% aqueous sodium carbonate (3×), water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationand concentrated
  8. additionHexane was added
  9. customto provide a precipitate
  10. customThe solid was collected
  11. custompurified by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-68f09e6ee277441aac32a3fcbc7987e5
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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