HCID 54358839, Verbindung → (2S)-2-{p-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzamido)pimelic acid

HRID 481436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481436
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][CH:13]([N:16]([C:20]4[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1.[NH2:29][C@@H:30]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])[C:31]([O:33]CC)=[O:32]>>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][CH:13]([N:16]([C:20]4[CH:21]=[CH:22][C:23]([C:24]([NH:29][C@@H:30]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[C:31]([OH:33])=[O:32])=[O:25])=[CH:27][CH:28]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1

Komponenten

3

Edukt 2

HCID 54358839HCID 54358839, VerbindungHCID 135443466p-[N-((6RS)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoic acid

Produkt 1

HCID 136351319(2S)-2-{p-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzamido)pimelic acidAusbeute 25 %

Versuchsvorschrift

Using an analogous procedure to that described in Example 3, p-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoic acid was coupled to diethyl (2S)-2-aminopimelate (J. Med. Chem., 1983, 26, 1719) and the resultant product was hydrolysed to give (2S)-2-{p-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzamido)pimelic acid in 25% yield, m.p. 165° C.;

Quellen und Nachweise

ORD-Eintrag
ord-7d261a156aaa477695e0939fc7bfaa76
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789417

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