4-Toluenesulfonyl chloride → HCID 57447032, compound

HRID 2366624Notes

Reaction equation

HRID 2366624 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:52]>>[NH2:52][C:9]1[C:8]2[N:17]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447033HCID 57447033, compound

Product 1

HCID 57447032HCID 57447032, compound

Procedure

6-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-N-propylhexanamide (4.1 g, 11 mmol) was treated with mCPBA (5.74 g, 33.3 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (2.85 g, 14.9 mmol) according to the method described in Part D of Example 8. The crude product was purified by column chromatography on silica gel (eluting with 97:3 dichloromethane:methanol) followed by recrystallization from methanol:water to provide 0.548 g of 6-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-N-propylhexanamide as beige needles, mp 161-162° C.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 97:3 dichloromethane:methanol)
  2. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-bb571e7ed4dd4c6f9593c0d97e57ec13
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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