Hydrazine → HCID 22063889, compound

HRID 1828164Notes

Reaction equation

HRID 1828164 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:15]([CH2:16][CH2:17][N:18]4C(=O)C5C(=CC=CC=5)C4=O)[CH:14]=[N:13][C:12]=3[C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)=[CH:10][C:5]=2[N:4]([CH3:36])[C:3]1=[O:37].NN>C(O)C>[NH2:18][CH2:17][CH2:16][N:15]1[C:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3](=[O:37])[N:4]([CH3:36])[C:5]=3[CH:10]=2)=[C:12]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[N:13]=[CH:14]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22063859HCID 22063859, compound

Product 1

HCID 22063889HCID 22063889, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred, hot solution of 2-{2-[5-(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-4-m-tolyl-imidazol-1-yl]-ethyl}-isoindole-1,3-dione (90 mg, 0.18 mmoles) in 5 mL ethanol was added aqueous 35 wt % hydrazine (50 pL). The resulting mixture was heated at reflux for 4 hours. The mixture (white precipitate visible) was cooled to 23° C. and concentrated in vacuo. The residue was taken up in 3 N HCl and methanol and extracted with ethyl acetate. The ethyl acetate extract was washed with 3 N HCl. The combined acidic aqueous layers were extracted with ethyl acetate (2 times). The acidic aqueous layer was made basic (pH 10–11) with Na2CO3 and extracted with ethyl acetate (3 times). These ethyl acetate extracts were combined and dried (Na2SO4), filtered, and the filtrate was concentrated to give 48 mg of 5-[3-(2-Amino-ethyl)-5-m-tolyl-3H-imidazol-4-yl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one as an off white film/solid. MS (APCI) m/z 362 (M+1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. concentrationconcentrated in vacuo
  4. extractionmethanol and extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with 3 N HCl
  7. extractionThe combined acidic aqueous layers were extracted with ethyl acetate (2 times)
  8. extractionextracted with ethyl acetate (3 times)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a75ec27aa14346599965099ed5863ebe
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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