4-Toluenesulfonyl chloride → HCID 58970356, compound

HRID 2366618Notes

Reaction equation

HRID 2366618 reaction equation
[CH3:1][O:2][CH2:3][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.C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:54]>>[CH3:1][O:2][CH2:3][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

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506694HCID 69506694, compound

Product 1

HCID 58970356HCID 58970356, compound

Procedure

2-(2-Methoxyethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline (4.55 g, 11.1 mmol) was treated with mCPBA (4.97 g, 21.6 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (3.69 g, 19.4 mmol) according to the method described in Part D of Example 8. The crude product was recrystallized twice from ethyl acetate to provide 1.17 g of 2-(2-methoxyethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 131-132° C.

Workup

  1. customThe crude product was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-b89a930545e347078f73c23b2540d80b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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