Indole-3-Carboxaldehyde → N-benzyl-2-[8,9-difluoro-4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-acetamide

HRID 900093Notes

Reaction equation

HRID 900093 reaction equation
[CH2:1]([N:8]([CH:35]([CH3:37])[CH3:36])[C:9](=[O:34])[CH2:10][N:11]1[C:20](=[O:21])[CH2:19][C:18]2[N:14]([C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:16][N:17]=2)[C:13]2[CH:28]=[C:29]([F:33])[C:30]([F:32])=[CH:31][C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]([CH:47]=O)=[CH:39]1>>[CH2:1]([N:8]([CH:35]([CH3:37])[CH3:36])[C:9](=[O:34])[CH2:10][N:11]1[C:20](=[O:21])[C:19](=[CH:47][C:40]2[C:41]3[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=3)[NH:38][CH:39]=2)[C:18]2[N:14]([C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:16][N:17]=2)[C:13]2[CH:28]=[C:29]([F:33])[C:30]([F:32])=[CH:31][C:12]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10256Indole-3-CarboxaldehydeHCID 58957934N-benzyl-2-(8,9-difluoro-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-acetamide

Product 1

HCID 136352447N-benzyl-2-[8,9-difluoro-4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-acetamideYield 75.7%

Procedure

Following the procedure described for Example 1(A), Step A, N-benzyl-2-(8,9-difluoro-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-acetamide (Preparation 9) (200 mg, 0.399 mmol) was condensed over 24 hours with 1H-indole-3-carbaldehyde (70 mg, 0.479 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (CH2Cl2 to 20% acetone in CH2Cl2) provided 190 mg of N-benzyl-2-[8,9-difluoro-4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-acetamide. MS 629.3 (M+1), 627.3 (M−1).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (CH2Cl2 to 20% acetone in CH2Cl2)

Sources & evidence

ORD record
ord-28afccdda1eb498e962fd3a990d857ec
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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