3-Methyl-4-anisaldehyde → (7bR,11aS)-N-(4-methoxy-3-methylbenzyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine

HRID 23279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23279
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19]3=[C:20]([CH2:22][O:23][CH2:24][CH2:25][N:18]3[C@H:17]3[CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][C@@H:16]23)[CH:21]=1>>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][NH:12][C:13]2[CH:14]=[C:15]3[C:19]4=[C:20]([CH2:22][O:23][CH2:24][CH2:25][N:18]4[C@H:17]4[CH2:26][CH2:27][NH:28][CH2:29][C@@H:16]34)[CH:21]=2)=[CH:3][C:2]=1[CH3:1]

Komponenten

3

Edukt 2

HCID 1229363-Methyl-4-anisaldehydeHCID 86586438Tert-butyl (7br,11as)-6-amino-1,2,7b,10,11,11a-hexahydro-4h-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8h)carboxylate

Produkt 1

HCID 60071845(7bR,11aS)-N-(4-methoxy-3-methylbenzyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine

Versuchsvorschrift

Using 3-methyl-4-methoxybenzaldehyde and following the procedures described in EXAMPLE 126, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H) carboxylate from EXAMPLE 56, Part B was converted into the title compound of EXAMPLE 136. 1H NMR (CDCl3) δ: 7.18-7.10 (m, 2H), 6.78 (d, 1H, J=9.2 Hz), 6.42 (d, 1H, J=1.9 Hz), 6.25 (d, 1H, J=2.2 Hz), 4.59 (ABq, 2H, JAB=14.1 Hz), 4.20-4.10 (m, 1H), 4.13 (s, 2H), 3.83 (s, 3H), 3.74 (app t, 1H), 3.30-3.23 (m, 1H), 3.22-3.10 (m, 2H), 3.09-3.01 (m, 1H), 2.95-2.88 (m, 2H), 2.62 (app t, 1H), 2.48 (app t, 1H), 2.21 (s, 3H), 2.00-1.80 (m, 2H). LRMS (ES)+: 380.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-f5dcf5d356404de6914b76feb5c9efee
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849619B2

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