4-Toluenesulfonyl chloride → HCID 57447031, compound

HRID 2366622Notes

Reaction equation

HRID 2366622 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]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[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+:54]>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:54])[C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506762HCID 69506762, compound

Product 1

HCID 57447031HCID 57447031, compound

Procedure

2-(Ethoxymethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline (4.4 g, 11 mmol) was treated with mCPBA (5.54 g, 32.1 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.74 g, 14.4 mmol) according to the method described in Part D of Example 8. The crude product was purified as described in Part D of Example 8 and then dried for two days at 60° C. to provide 1.061 g of 2-(ethoxymethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinolin-4-amine as a beige powder, mp 160-162° C.

Workup

  1. customThe crude product was purified
  2. customdried for two days at 60° C.

Sources & evidence

ORD record
ord-2ae36fa70be347bd914862af9fd83e67
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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