4-Toluenesulfonyl chloride → HCID 57447044, compound

HRID 2366651Notes

Reaction equation

HRID 2366651 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:37].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O>[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][C:17]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:18])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:37])[C:5]=2[N:14]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447046HCID 57447046, compound

Product 1

HCID 57447044HCID 57447044, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline (4.8 g, 15 mmol) was treated with mCPBA (5.95 g, 25.9 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (5.49 g, 28.8 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. After the amination reaction was stirred for two hours, water was added. Following the work-up procedure, the chromatographic purification was carried out eluting with 90:10 dichloromethane:methanol. The resulting product was triturated with ethyl acetate and isolated by filtration to provide 2-methyl-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 166-169° C.

Workup

  1. washThe reaction was not washed with 10% aqueous sodium hydroxide
  2. additionto the addition of ammonium hydroxide
  3. customAfter the amination reaction
  4. customthe chromatographic purification
  5. washwas carried out eluting with 90:10 dichloromethane
  6. customThe resulting product was triturated with ethyl acetate
  7. customisolated by filtration

Sources & evidence

ORD record
ord-6b1a76372cb44919a546f055ed7f12ee
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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