4-Toluenesulfonyl chloride → HCID 58970381, compound

HRID 2366654Notes

Reaction equation

HRID 2366654 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])[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+:51]>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][C:20]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[O:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:51])[C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506687HCID 69506687, compound

Product 1

HCID 58970381HCID 58970381, compound

Procedure

2-(Ethoxymethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline (5.1 g, 14 mmol) was treated with mCPBA (5.57 g, 24.2 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (5.14 g, 26.9 mmol) according to a modification of the method described in Part D of Example 8. The reaction was not washed with 10% aqueous sodium hydroxide prior to the addition of ammonium hydroxide. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol) and then triturated with ethyl acetate and isolated by filtration to provide 0.843 g of 2-(ethoxymethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles, mp 187-189° C.

Workup

  1. washThe reaction was not washed with 10% aqueous sodium hydroxide
  2. additionto the addition of ammonium hydroxide
  3. customThe crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  4. customtriturated with ethyl acetate
  5. customisolated by filtration

Sources & evidence

ORD record
ord-93912eb747294fe596e1a39350c9e900
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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