Indole-3-Carboxaldehyde → 2-[1-cyclohexyl-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 900112Notes

Reaction equation

HRID 900112 reaction equation
[CH:1]1([C:7]2[N:16]3[C:10]([CH2:11][C:12](=[O:34])[N:13]([CH2:21][C:22]([N:24]([CH:31]([CH3:33])[CH3:32])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([CH:44]=O)=[CH:36]1>>[CH:1]1([C:7]2[N:16]3[C:10]([CH:11]([CH2:44][C:37]4[C:38]5[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=5)[NH:35][CH:36]=4)[C:12](=[O:34])[N:13]([CH2:21][C:22]([N:24]([CH:31]([CH3:32])[CH3:33])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10256Indole-3-CarboxaldehydeHCID 693139642-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide

Product 1

HCID 236606712-[1-cyclohexyl-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

Procedure

Following the procedure described for Example 6(A), Step A; 2-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide (Preparation 8(B)) was condensed with 1H-indole-3-carbaldehyde. This intermediate was carried forward according to Example 6(A) Step B to afford 2-[1-cyclohexyl-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 8.44 (s, 1H), 7.42-7.48 (m, 4H), 7.28-7.42 (m, 4H), 7.17-7.19 (m, 2H), 7.07-7.10 (m, 1H), 6.98-7.02 (m, 1H), 4.90-4.94 (m, 1H), 4.07-4.15 (m, 1H), 3.91 (d, 1H), 3.67-3.73 (m, 2H), 2.83 (br.m, 1H), 2.19 (br.m, 1H), 1.89-1.92 (m, 2H), 1.68 (br.s, 4H), 1.50-1.59 (m, 1H), 1.32-1.35 (m, 2H), 1.23 (t, 1H), 1.06 (m, 6H); MS 587 (M+1).

Sources & evidence

ORD record
ord-147822869d2447f5b06adb7c1770c89b
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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