Ammonium Hydroxide → (7Br,11as)-n-(3-quinolinyl)-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 23270

Reaktionsgleichung

Reaktionsgleichung von HRID 23270
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[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.[OH-].[NH4+]>>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([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]=1

Komponenten

4

Edukt 3

HCID 14923Ammonium HydroxideHCID 214133-BromoquinolineHCID 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 60071890(7Br,11as)-n-(3-quinolinyl)-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-bromoquinoline and following the procedures described in EXAMPLE 56, Part C, 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 (7bR,11aS)-N-(3-quinolinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine, bis-trifluoroacetic acid salt. This material was free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to afford the title compound of EXAMPLE 114. 1H NMR (CDCl3) δ: 8.60 (d, 1H, J=2.9 Hz), 7.95 (d, 1H, J=1.9 Hz), 7.60-7.55 (m, 1H), 7.50-7.38 (m, 3H), 6.88 (d, 1H, J=1.9 Hz), 6.81 (s, 1H), 5.99 (s, 1H4), 5.85 (broad s, 1H), 4.61 (ABq, 2H, JAB=14.7 Hz), 4.23 (app d, 1H, J=12.4 Hz), 3.74 (app t, 1H), 3.43 (broad s, 1H), 3.30-3.00 (m, 4H), 2.75 (app t, 1H), 2.65-2.55 (m, 1H), 2.20-1.90 (m 3H). LRMS (ES)+: 373.4 (M+H)+.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washwashed with brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a4d0d6545c748feb7047a8866830731
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849619B2

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