N-Benzylethylenediamine → HCID 86758121, Verbindung

HRID 2184937

Reaktionsgleichung

Reaktionsgleichung von HRID 2184937
C([NH:8][CH2:9][CH2:10][NH2:11])C1C=CC=CC=1.[CH2:12]([N:14]1[C:26]2[CH:25]=[CH:24][C:23]([C:27]([OH:29])=O)=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13]>>[NH2:8][CH2:9][CH2:10][NH:11][C:27]([C:23]1[CH:24]=[CH:25][C:26]2[N:14]([CH2:12][CH3:13])[C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:29]

Komponenten

3

Edukt 2

HCID 77801N-BenzylethylenediamineHCID 49128699-Ethyl-9H-carbazole-3-carboxylic acid

Produkt 1

HCID 86758121HCID 86758121, VerbindungAusbeute 92 %

Versuchsvorschrift

N1-Benzyl-ethane-1,2-diamine (6.0 g, 25.1 mmol) was coupled with 9-Ethyl-9H-carbazole-3-carboxylic acid as described in example 81 to afford, after chromatographic purification (silica; 3% MeOH/CH2Cl2) 9-Ethyl-9H-carbazole-3-carboxylic acid (2-benzylamino-ethyl)-amide (4.5 g, 48%) (MS m/z @ 372 (m+1). This material was subjected to catalytic hydrogenation ((10%Pd—C/H2 @ 50 psi) in EtOH/AcOH to afford 9-Ethyl-9H-carbazole-3-carboxylic acid (2-amino-ethyl)-amide (3.16 g, 92%) as a white solid MS m/z @ 282 (m+1). This material was reductively aminated using sodium triacetoxyborohydride and thiazole-2-carbaldehyde similarly to conditions described for example 75 to afford the title compound (350 mg, 65%). MS m/z @ 379 (m+1).

Aufarbeitung

  1. customto afford
  2. customafter chromatographic purification (silica; 3% MeOH/CH2Cl2) 9-Ethyl-9H-carbazole-3-carboxylic acid (2-benzylamino-ethyl)-amide (4.5 g, 48%) (MS m/z @ 372 (m+1)

Quellen und Nachweise

ORD-Eintrag
ord-09ec29c84c7b4dc0b7f3b4748dc20780
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399631B1

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