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

HRID 900092Notes

Reaction equation

HRID 900092 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]3[C:11]([CH2:12][C:13](=[O:35])[N:14]([CH2:22][C:23]([N:25]([CH:32]([CH3:34])[CH3:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:24])[C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=43)=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=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>>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]3[C:11]([C:12](=[CH:45][C:38]4[C:39]5[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=5)[NH:36][CH:37]=4)[C:13](=[O:35])[N:14]([CH2:22][C:23]([N:25]([CH:32]([CH3:33])[CH3:34])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:24])[C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=43)=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10256Indole-3-CarboxaldehydeHCID 58957933HCID 58957933, compound

Product 1

HCID 1363524462-[1-(3-hydroxy-phenyl)-4-(1H-indol-3-ylmethylene)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamideYield 57.3%

Procedure

Following the procedure described for Example 1(A), Step A, 2-[1-(3-hydroxy-phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide (Preparation 12) (244 mg, 0.522 mmol) was condensed over 48 hours with 1H-indole-3-carbaldehyde (105 mg, 0.723 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (EtOAc to 5% MeOH in EtOAc to 10% MeOH in EtOAc) yielded 177.9 mg of 2-[1-(3-hydroxy-phenyl)-4-(1H-indol-3-ylmethylene)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD3OD) δ 8.23 (d, 1H), 7.90 (s, 1H), 6.90-7.63 (m, 16H), 4.95 (m, 1H), 3.68-4.50 (m, 3H), 1.11 (m, 6H); MS 595.3 (M+1), 593.3 (M−1).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (EtOAc to 5% MeOH in EtOAc to 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-4527538393ae424193f47edcb82c35a8
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

Loading…