Benzenesulfonyl chloride → HCID 58970355, Verbindung

HRID 2366710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366710
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[C:7]1[CH2:19][CH2:20][CH3:21].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[NH4+:46]>>[NH2:46][C:10]1[C:9]2[N:8]=[C:7]([CH2:19][CH2:20][CH3:21])[N:6]([CH2:5][CH2:4][C:3]([N:2]([CH3:1])[CH3:23])=[O:22])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Komponenten

5

Edukt 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447094HCID 57447094, Verbindung

Produkt 1

HCID 58970355HCID 58970355, Verbindung

Versuchsvorschrift

N,N-Dimethyl-3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (2.40 g, 7.73 mmol) was treated with mCPBA (3.11 g, 13.5 mmol), ammonium hydroxide (40 mL), and benzenesulfonyl chloride (1.92 mL, 15.1 mmol) according to the method described in Part D of Example 36. The crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol) to provide 0.097 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N,N-dimethylpropanamide as a tan powder, mp 207-209° C.

Aufarbeitung

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-a54ef8e37d1c41eeb898ccda58db3bce
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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