Indole-3-Carboxaldehyde → 2-[1-(2-fluoro-phenyl)-4-(1H-indol-3-ylmethyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

HRID 900113

Reaktionsgleichung

Reaktionsgleichung von HRID 900113
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]2[C:11]([CH2:12][C:13](=[O:35])[N:14]([CH2:22][C:23]([N:25]([CH:32]([CH3:34])[CH3:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=32)=[N:10][N:9]=1.[NH:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([CH:45]=O)=[CH:37]1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]2[C:11]([CH:12]([CH2:45][C:38]3[C:39]4[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=4)[NH:36][CH:37]=3)[C:13](=[O:35])[N:14]([CH2:22][C:23]([N:25]([CH:32]([CH3:33])[CH3:34])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:24])[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=32)=[N:10][N:9]=1

Komponenten

3

Edukt 2

HCID 10256Indole-3-CarboxaldehydeHCID 693140432-(1-(2-fluorophenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide

Produkt 1

HCID 236604972-[1-(2-fluoro-phenyl)-4-(1H-indol-3-ylmethyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

Versuchsvorschrift

Following the procedure described for Example 6(A), Step A; 2-(1-(2-fluorophenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide (Preparation 7(B)) was condensed with 1H-indole-3-carbaldehyde. This intermediate was carried forward according to Example 6(A) Step B to afford 2-[1-(2-fluoro-phenyl)-4-(1H-indol-3-ylmethyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD2Cl2) δ 8.26 (s, 1H), 7.71-7.74 (m, 1H), 7.60-7.67 (m, 2H), 7.40-7.59 (m, 6H), 7.34-7.38 (m, 2H), 7.23-7.32 (br. m, 2H), 7.14-7.20 (m, 1H), 7.05-7.12 (m, 3H), 6.81-6.83 (m, 1H), 4.98-5.03 (m, 1H), 4.28 (d, 1H), 3.93 (d, 1H), 3.83-3.84 (m, 3H), 1.12 (d, 6H); MS 599 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-44bb152db0444422ad4204bee2e586ef
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358242B2

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