Acetic Acid → N-(4-aminobenzyl)amino-1H-benzimidazole

HRID 19518

Reaction equation

HRID 19518 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](C=O)=[CH:6][CH:5]=1)([O-])=O.[C:12](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH2:30][C:31]1[CH:39]=[C:38]2[C:34]([CH:35]=[N:36][NH:37]2)=[CH:33][CH:32]=1>ClCCl>[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][NH:36][N:37]2[C:5]3[CH:6]=[CH:7][CH:10]=[CH:11][C:4]=3[N:1]=[CH:12]2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 814231H-Indazol-6-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17864618N-(4-aminobenzyl)amino-1H-benzimidazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 0.145 g (0.98 mmol) of 4-nitrobenzaldehyde in 3 ml of dichloromethane was added 0.31 g (1.47 mmol) of sodium triacetoxyborohydride, 0.6 ml (0.98 mmol) of acetic acid and 0.13 g (0.98 mmol) of 6-aminoindazole. After stirring the mixture overnight at room temperature, the solvent was evaporated. The resulting residue was dissolved in 10 ml of ethanol, 20 mg of 10% palladium on carbon was added and stirred under hydrogen atmosphere overnight. The catalyst was filtered off through celite. After evaporation of the solvent the residue was purified by HPLC and lyophilized to yield 0.2 g (86%) of the title compound. 1H-NMR (CDCl3) δ: 4.12 (2H, br), 6.50-6.70 (5H, m), 7.52 (1H, d), 7.86-7.94 (2H, m), 8.18 (1H, br), 8.29 (1H, br).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe resulting residue was dissolved in 10 ml of ethanol
  3. addition20 mg of 10% palladium on carbon was added
  4. stirringstirred under hydrogen atmosphere overnight
  5. filtrationThe catalyst was filtered off through celite
  6. customAfter evaporation of the solvent the residue
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-e3caf4afabd54e539ab301437c037bbb
Source dataset
uspto-grants-2010_06
Patent number
US07745443B2

Linked notes

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