4-Toluenesulfonyl chloride → HCID 57447029, compound

HRID 2366614Notes

Reaction equation

HRID 2366614 reaction equation
[N:1]1([C:7](=[O:26])[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]=[CH:14]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:50]>>[N:1]1([C:7](=[O:26])[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]([NH2:50])[C:16]=3[N:15]=[CH:14]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447028HCID 57447028, compound

Product 1

HCID 57447029HCID 57447029, compound

Procedure

1-(6-Morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline (3.09 g, 8.79 mmol) was treated with mCPBA (3.54 g, 15.4 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (3.26 g, 17.4 mmol) according to the method described in Part D of Example 8. The crude product was purified as described in Part C of Example 10 to provide 0.422 g of 1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 166-168° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-0cc7a4115f814830b832f242e193c069
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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