2-(3,4-Diaminobenzyl)isoindole-1,3-dione → HCID 178524164, compound

HRID 412690Notes

Reaction equation

HRID 412690 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[NH2:20])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].C(O[C:24]([CH2:26][C:27]1[NH:31][C:30]2[CH:32]=[CH:33][C:34]([C:36]([OH:38])=[O:37])=[CH:35][C:29]=2[N:28]=1)=O)C>C(Cl)Cl.C(O)C>[O:16]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14](=[O:15])[N:6]1[CH2:5][C:4]1[CH:17]=[CH:18][C:19]2[NH:20][C:24]([CH2:26][C:27]3[NH:31][C:30]4[CH:32]=[CH:33][C:34]([C:36]([OH:38])=[O:37])=[CH:35][C:29]=4[N:28]=3)=[N:1][C:2]=2[CH:3]=1

Participants

4

Reactant 2

HCID 185377612-(3,4-Diaminobenzyl)isoindole-1,3-dioneHCID 178470774HCID 178470774, compound

Product 1

HCID 178524164HCID 178524164, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Conditions

Temperature
185 °C

Procedure

A finely ground mixture of 2-(3,4-diaminobenzyl)isoindole-1,3-dione (2.0 g, 7.5 mmol) and 2-ethoxycarbonylmethyl-1H-benzimidazole-5-carboxylic acid (0.93 g, 3.75 mmol) was heated 1 hour at 185° C. under nitrogen. The mixture was suspended in 1:1 methylene chloride/ethanol (20 mL) and stirred vigorously for 1 hour. The solids were collected by filtration, washed with 1:1 methylene chloride/ethanol (3×20 mL) and dried to provide 2-[5-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-1H-benzoimidazole-5-carboxylic acid (0.98 g, 29% yield); 1H-NMR (300 Mhz, DMSO-d6): 12.45 (broad s, 1H), 8.07 (s, 1H), 7.80-7.83 (m, 6H), 7.51 (d, 1H, J=7.5 Hz), 7.43 (s, 1H), 7.11 (d, 1H, J=7.2 Hz), 4.82 (s, 2H), 4.48 (s, 2H).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with 1:1 methylene chloride/ethanol (3×20 mL)
  3. customdried

Sources & evidence

ORD record
ord-8e787cc2bba4466d91fc70bfe83f11b7
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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