Sodium hydride → HCID 15342538, Verbindung

HRID 1417965Notizen

Reaktionsgleichung

[CH3:1][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:3].[H-].[Na+].[CH3:33][N:34]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35](=[O:38])[CH2:36]Br>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[N:11]([CH2:36][C:35]([N:34]([CH3:33])[CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:1]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2.1 g of 5-benzyloxy-4-methoxymethyl-9H-pyrido-[3,4-b]indole-3-carboxylic acid-(1-methylethyl)ester is added to a suspension of 168 mg of sodium hydride (80% in mineral oil) in 25 ml of tetrahydrofuran at 0° C., it is stirred for 10 minutes at 0° C., then mixed with a solution of 1.6 g of N-methyl-N-2-phenylethyl-2-bromoacetamide and stirred for 18 hours at 24° C. Then, it is suctioned off on Celite, concentrated by evaporation in a vacuum, and the residue is purified by chromatography on silica gel. 2.8 g of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained as weak, yellowish crystals with a melting point of 146°-147° C.

Aufarbeitung

stirringstirred for 18 hours at 24° C
concentrationconcentrated by evaporation in a vacuum
customthe residue is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-4dd22972defc46208c984fd9e050e4c2
Quelldatensatz: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05880126

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