HCID 178507224, compound → HCID 10468857, compound

HRID 2299157Notes

Reaction equation

HRID 2299157 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1>C(O)C(C)C>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([NH:11][C:8]2[NH:9][CH2:10][CH2:6][N:7]=2)[CH:3]=1

Participants

3

Reactant 1

HCID 178507224HCID 178507224, compound

Product 1

HCID 10468857HCID 10468857, compoundYield 157.9%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

4-bromo-6-aminobenzimidazole (0.4 g, 1.9 mmol) and ISA (1.2 g, 8.9 mmol) was dissolved in isobutanol and stirred at reflux for 12 h. Column chromatographic separation of the reaction mixture (NH3 sat'd 20% MeOH/EtOAc) provided 0.41 g (1.5 mmol, 78%) of the product. The product obtained was converted to the fumarate salt and recrystallized from isopropanol to afford 0.24 g (32%) of the product as a light brown solid: mp 217-218° C.; Anal. Calc. for C10H10N5Br.1.0C4H4O4 requires C, 42.44; H, 3.56; N, 17.68. Found: C, 42.28; H. 3.58; N, 17.40.

Workup

  1. temperatureat reflux for 12 h
  2. customColumn chromatographic separation of the reaction mixture (NH3 sat'd 20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-4f5382fd2a7a403896c74171b436bb93
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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