4-Toluenesulfonyl chloride → HCID 57447023, compound

HRID 2366608Notes

Reaction equation

HRID 2366608 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[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][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[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 57447024HCID 57447024, compound

Product 1

HCID 57447023HCID 57447023, compound

Procedure

6-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (1.7 g, 5.2 mmol) was treated with mCPBA (3.61 g, 15.7 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (1.49 g, 7.84 mmol) according to the method described in Part D of Example 8. The crude product was purified as described in Part D of Example 8 to provide 0.137 g of 6-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide as tan needles, mp 210-211° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-9ad5696a95334f7ba52ed4599f3de9fc
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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