Thionyl Chloride → N-((9H-pyrido[3,4-b]indol-1-yl)methyl)-N-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride

HRID 628670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628670
[C:1]1([CH2:14][N:15]([CH:28]2[C:37]3[N:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:31][CH2:30][CH2:29]2)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.S(Cl)([Cl:40])=O>CO>[ClH:40].[ClH:40].[ClH:40].[ClH:40].[C:1]1([CH2:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:28]2[C:37]3[N:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:31][CH2:30][CH2:29]2)[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 59176352tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

Produkt 1

HCID 68715314N-((9H-pyrido[3,4-b]indol-1-yl)methyl)-N-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochlorideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)-butylcarbamate, 4, (0.12 g, 0.24 mmol) in methanol (5 mL) was treated with thionyl chloride (1 mL) at room temperature. The resulting mixture was stirred for 30 min. The reaction mixture was then concentrated and dried under reduced pressure to afford 0.11 g (80% yield) of the desired product A: 1H NMR (400 MHz, d6-DMSO) δ 13.49 (bs, 1H), 8.80-8.41 (m, 3H), 8.00-7.82 (m, 3H), 7.80 (d, J=8.0 Hz, 1H), 7.78-7.70 (m, 1H), 7.39 (t, J=7.2 Hz, 1H), 4.95-4.85 (m, 1H), 4.68-4.50 (m, 2H), 2.98-2.82 (m, 2H), 2.61-2.50 (m, 2H), 2.47-2.35 (m, 3H), 2.12-1.94 (m, 2H), 1.80-1.30 (m, 5H); ESI+ MS: m/z (rel intensity) 400.2 (100, [M+H]+).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c31b96b3bcb4f5082f58e81d0128eb9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09314468B2

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