4-Toluenesulfonyl chloride → HCID 57447035, compound

HRID 2366629Notes

Reaction equation

HRID 2366629 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:48]>>[NH2:48][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506709HCID 69506709, compound

Product 1

HCID 57447035HCID 57447035, compound

Procedure

3-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylpropanamide (3.5 g, 11 mmol) was treated with mCPBA (5.85 g, 32.4 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.76 g, 14.6 mmol) according to a modification of the method described in Part D of Example 8. When the reaction was complete, the organic layer was separated, washed with 10% aqueous sodium bicarbonate, and concentrated under reduced pressure. The crude product was purified as described in Part D of Example 8 to provide 1.026 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylpropanamide as beige needles, mp 157-158° C.

Workup

  1. customthe organic layer was separated
  2. washwashed with 10% aqueous sodium bicarbonate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-ad05812f89fb43639f914d4b95bf94af
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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