5-(Piperazin-1-yl)benzofuran-2-carboxamide → Vilazodone

HRID 2404951

Reaktionsgleichung

Reaktionsgleichung von HRID 2404951
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([NH2:17])=[O:16])=[CH:12][C:11]=3[CH:18]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:33]#[N:34])[CH:31]=2)[NH:26][CH:25]=1>>[CH:29]1[C:30]([C:33]#[N:34])=[CH:31][C:32]2[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][N:4]3[CH2:3][CH2:2][N:1]([C:7]4[CH:8]=[CH:9][C:10]5[O:14][C:13]([C:15]([NH2:17])=[O:16])=[CH:12][C:11]=5[CH:18]=4)[CH2:6][CH2:5]3)=[CH:25][NH:26][C:27]=2[CH:28]=1

Komponenten

3

Edukt 2

HCID 98347195-(Piperazin-1-yl)benzofuran-2-carboxamideHCID 98811233-(4-Chlorobutyl)-5-cyanoindole

Produkt 1

HCID 6918314Vilazodone

Versuchsvorschrift

A second related synthesis route provided for hydrogenation of the 5-nitrobenzofuran-2-carboxylic acid ethyl ester with Raney nickel and H2 in MeOH to give the corresponding compound of 5-aminobenzofuran with bis(2-chloroethyl) amine in dichloromethane to give 5-(1-piperazinyl)-benzofuran-2-carboxylic acid ethyl ester. The reaction of the latter compound with di-tert-butyl dicarbonate in THF provides the protected amino compound 5-[4-(tert-butoxycarbonyl)-1-piperazinyl]benzofuran-2-carboxylic acid ethyl ester, which is first reacted with formamide and sodium alkoxide in N-methylpyrrolidone to provide the corresponding amide, and then deprotected by treatment with HCl/MeOH to give 5-(1-piperazinyl)benzofuran-2-carboxamide. Finally, this amide is condensed with 3-(4-chlorobutyl)-1H-indol-5-carbonitrile to give vilazodone.

Quellen und Nachweise

ORD-Eintrag
ord-a9c6c495cc7d46fcba5a4ff00f0a43e1
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802851B2

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