4-Toluenesulfonyl chloride → HCID 58970358, compound

HRID 2366642Notes

Reaction equation

HRID 2366642 reaction equation
[CH3:1][O:2][CH2:3][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.C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:51]>>[CH3:1][O:2][CH2:3][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

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506732HCID 69506732, compound

Product 1

HCID 58970358HCID 58970358, compound

Procedure

2-(2-Methoxyethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline (4.7 g, 13 mmol) was treated with mCPBA (5.73 g, 24.9 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (4.23 g, 22.2 mmol) according to the method described in Part D of Example 8. The crude product was recrystallized twice from ethyl acetate to provide 0.233 g of 2-(2-methoxyethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-4-amine as beige needles, mp 125-126° C.

Workup

  1. customThe crude product was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-c6366de9b44342a698863bab77b76987
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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