4-Toluenesulfonyl chloride → HCID 57447016, compound

HRID 2366600Notes

Reaction equation

HRID 2366600 reaction equation
[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:18]=[CH:17][C:16]=3[N:15]=[C:14]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:42].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:18]=[C:17]([NH2:42])[C:16]=3[N:15]=[C:14]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506816HCID 69506816, compound

Product 1

HCID 57447016HCID 57447016, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, a solution of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinoline (3.6 g, 9.1 mmol) in chloroform (100 mL) was treated with mCPBA (6.29 g, 36.5 mmol). The reaction was stirred for two hours, washed sequentially with saturated aqueous sodium bicarbonate (3×) and brine, dried over magnesium sulfate, and filtered. Concentrated ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.60 g, 13.7 mmol) were added sequentially to the filtrate. The reaction was stirred vigorously for two hours, and then the organic layer was separated and washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) followed by recrystallization from ethyl acetate:hexane to provide 0.84 g of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 149-151° C.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate (3×) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. stirringThe reaction was stirred vigorously for two hours
  5. customthe organic layer was separated
  6. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
  11. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-aaddb133218e41bea7049d346d6e8c11
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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