o-(Trifluoromethyl)benzaldehyde → (7bR,11aS)-N-[2-(trifluoromethyl)benzyl]-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 47558

Reaktionsgleichung

Reaktionsgleichung von HRID 47558
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20]3=[C:21]([CH2:23][O:24][CH2:25][CH2:26][N:19]3[C@H:18]3[CH2:27][CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][C@@H:17]23)[CH:22]=1>>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:13][C:14]1[CH:15]=[C:16]2[C:20]3=[C:21]([CH2:23][O:24][CH2:25][CH2:26][N:19]3[C@H:18]3[CH2:27][CH2:28][NH:29][CH2:30][C@@H:17]23)[CH:22]=1

Komponenten

3

Edukt 2

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 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 60071863(7bR,11aS)-N-[2-(trifluoromethyl)benzyl]-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 2-(trifluoromethyl)benzaldehyde 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 128. 1H NMR(CDCl3) δ: 7.72-7.60 (m, 2H), 7.52 (t, 1H, J=7.7 Hz), 7.38 (t, 1H, J=7.5 Hz), 6.39 (d, 1H, J=1.8 Hz), 6.21 (d, 1H, J=1.8 Hz), 4.57 (ABq, 2H, JAB=14.3 Hz), 4.50 (s, 2H), 4.20 (app d, 1H, J=12.0 Hz), 3.74 (app t, 1H), 3.36-3.30 (m, 1H), 3.28-3.18 (m, 2H), 3.08 (dd, 1H, J=12.5, 6.2 Hz), 3.00-2.90 (m, 2H), 2.65 (app t, 1H), 2.50 (app t, 1H), 2.02-1.90 (m, 2H). LRMS (ES)+: 404.3 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-3716061722c7468cb166ac176285e1e8
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699852B2

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