2-(2-Bromo-5-methoxyphenyl)-2-methyl-1,3-dioxolane → 1-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methoxyphenyl}ethanone

HRID 23273

Reaktionsgleichung

Reaktionsgleichung von HRID 23273
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1([CH3:15])[O:14]CCO1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23]3=[C:24]([CH2:26][O:27][CH2:28][CH2:29][N:22]3[C@H:21]3[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][C@@H:20]23)[CH:25]=1>>[CH2:29]1[N:22]2[C:23]3[C:19]([C@@H:20]4[CH2:33][NH:32][CH2:31][CH2:30][C@@H:21]42)=[CH:18][C:17]([NH:16][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[C:10](=[O:14])[CH3:15])=[CH:25][C:24]=3[CH2:26][O:27][CH2:28]1

Komponenten

3

Edukt 2

HCID 149376932-(2-Bromo-5-methoxyphenyl)-2-methyl-1,3-dioxolaneHCID 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 600718321-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methoxyphenyl}ethanone

Versuchsvorschrift

Using 2-(2-bromo-5-methoxyphenyl)-2-methyl-1,3-dioxolane and following the procedures described in EXAMPLE 116, 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 118. 1H NMR (CDCl3) o: 9.95 (s, 1H), 7.22 (d, 1H, J=2.5 Hz), 6.99-6.92 (m, 2H), 6.86 (d, 1H, J=1.8 Hz), 6.75 (d, 1H, J=1.9 Hz), 4.58 (ABq, 2H, JAB=14.2 Hz), 4.20 (app d, 1H), 3.77 (s, 3H), 3.72 (app t, 1H), 3.42-3.37 (m, 1H), 3.35-3.20 (m, 2H), 3.10 (dd, 1H), 3.01-2.90 (m, 2H), 2.71 (app t, 1H), 2.59 (s, 3H), 2.50 (app t, 1H), 2.02-1.90 (m, 2H). LRMS (ES)+: 394.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-9c15ec6f96d04a43a4b3161e45fc413e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849619B2

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