3-Fluorobenzenesulfonamide → N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride

https://huagongshe.com/de/reaction/230498

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	3-Fluorobenzenesulfonamide	HCID 150924	—
Edukt	3-Fluorobenzenesulfonyl Chloride	HCID 2734258	—
Edukt	Ether hydrochloride	HCID 10953452	—
Edukt	Tert-butyl 4-(3,4-diaminophenyl)-1,4-diazepane-1-carboxylate	HCID 22272464	—
Edukt	N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}3-fluorobenzenesulfonamide	HCID 22272531	—
Lösungsmittel	Methanol	HCID 887	—
Produkt	N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride	HCID 10209725	—

Reaktionsschritte

The compound was prepared from 2-amino-5-(4-t-butyloxycarbonyl-1-homopiperazinyl)aniline and 3-flourobenzenesulfonyl chloride. Purification by column chromatography (CH2Cl2/MeOH/heptane, 4:1:15) gave a mixture of N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}3-fluorobenzenesulfonamide and N-{4-[4-t-butyloxycarbonyl]homopiperazinyl)-2-[(3-flourophenylsulfonyl)amino]phenyl}-3-fluorobenzenesulfonamide (0.180 g, 73%). Boc-deprotection was achieved by dissolving the mixture in small amount of MeOH and adding HCl/ether. The mixture was let at r.t. for 0.5 h. Purification by preparative HPLC gave N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride Anal. (C23H27ClN4O4S2) C, H, N, S.; M+524.4 Calcd 522.12.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07566715B2
Quelldatensatz	uspto-grants-2009_07
ORD ID	ord-57fe2d3a47c44f80bca77a742dc4f261
Quellennotiz	uspto-grants-2009_07