4-Toluenesulfonyl chloride → HCID 57447036, compound

HRID 2366633Notes

Reaction equation

HRID 2366633 reaction equation
[N:1]1([C:7](=[O:26])[CH2:8][CH2:9][N:10]2[C:22]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[N:15]=[CH:14][C:13]=3[N:12]=[C:11]2[CH2:23][CH2:24][CH3:25])[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][N:10]2[C:22]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[N:15]=[C:14]([NH2:50])[C:13]=3[N:12]=[C:11]2[CH2:23][CH2:24][CH3:25])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447037HCID 57447037, compound

Product 1

HCID 57447036HCID 57447036, compound

Procedure

1-(3-Morpholin-4-yl-3-oxopropyl)-2-propyl-1H-imidazo[4,5-c]quinoline (5.2 g, 15 mmol) was treated with mCPBA (7.64 g, 44.3 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (3.79 g, 19.9 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 95:5 dichloromethane:methanol) followed by recrystallization from methanol:dichloromethane to provide 0.358 g of 1-(3-morpholin-4-yl-3-oxopropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as yellow needles, mp 172-173° C.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
  2. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-0cb7eb7498b741cd8659c13b13475906
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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