4-Toluenesulfonyl chloride → HCID 58970365, compound

HRID 2366611Notes

Reaction equation

HRID 2366611 reaction equation
[N:1]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.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:5]1[C:4]2[N:3]=[CH:2][N:1]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447026HCID 57447026, compound

Product 1

HCID 58970365HCID 58970365, compound

Procedure

6-(1H-Imidazo[4,5-c]quinolin-1-yl)-N-propylhexanamide (7.0 g, 26 mmol) was treated with mCPBA (8.68 g, 37.7 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (8.01 g, 42.1 mmol) according to the method described in Part D of Example 8. The crude product was triturated with ethyl acetate and recrystallized twice from methanol:water to provide 2.00 g of 6-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylhexanamide as brown needles, mp 128-130° C.

Workup

  1. customThe crude product was triturated with ethyl acetate
  2. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-5af62c2b9467412393b03545e71be2d6
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…