HCID 66593271, compound → HCID 66593257, compound

HRID 1091638Notes

Reaction equation

HRID 1091638 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][C:3]=1[N+:17]([O-])=O>C(O)C.[Pd]>[NH2:17][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 66593271HCID 66593271, compound

Product 1

HCID 66593257HCID 66593257, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1H-imidazole-1-ylacetic acid (284 mg, 2.25 mmol) and 2-nitrobenzene-1,4-diamine (324 mg, 2.12 mmol) in acetonitrile (20 mL) was added 3-diethoxyphosphoryloxy-1,2,3-benzotriazin-4(3H)-one (DEPBT, 632 mg, 2.11 mmol) and triethylamine (600 μL, 4.4 mmol). The mixture was stirred for 4 d at room temperature. The red precipitate was collected by filtration and washed with acetonitrile to give N-(4-amino-3-nitrophenyl)-2-(1H-imidazol-1-yl)acetamide (430 mg, 88% yield), 98% pure. A solution of N-(4-amino-3-nitrophenyl)-2-(1H-imidazol-1-yl)acetamide (430 mg, 1.65 mmol) in ethanol (20 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (100 mg, 0.09 mmol) at room temperature overnight. The mixture was filtered, giving a blue solution. Removal of the solvent under reduced pressure gave N-(3,4-diaminophenyl)-2-(1H-imidazol-1-yl)acetamide (413 mg) as a blue semi-solid.

Workup

  1. filtrationThe mixture was filtered
  2. customgiving a blue solution
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-86cd6bf4070b488d8188020e44f19150
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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