Hydrazine → HCID 178448430, compound

HRID 1966727Notes

Reaction equation

HRID 1966727 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]([C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[C:11](/[N:13]=[CH:14]/[N:15](C)C)=O)=[N:8][C:4]=2[CH:3]=1.[NH2:28]N>C(O)(=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:22]([CH3:24])([CH3:23])[CH3:25])[C:7]([C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[C:11]3[N:13]=[CH:14][NH:15][N:28]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 178484330HCID 178484330, compound

Product 1

HCID 178448430HCID 178448430, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-[1-dimethylamino-meth-(E)-ylidene]-benzamide (230 mg, 0.538 mmol) in glacial acetic acid (3 mL), followed by the addition of hydrazine (35% wt solution in water) (2 mL). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc, washed with sat. NaHCO3 and brine, dried under Na2SO4, filtered and concentrated. The residue is loaded onto a silica gel column. The column is eluted with 0-4% 2M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford 5-bromo-1-tert-butyl-2-[2-(1H-1,2,4-triazol-3-yl)-phenyl]-1H-benzimidazole (180 mg, 84%) as an off-white solid. LCMS (ESMS): m/z 396.68, 398.64 (M++1)

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. customdried under Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe column is eluted with 0-4% 2M NH3 in MeOH/CH2Cl2
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-43bffc242d4a4c4494bffe8befc6c881
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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