Water → HCID 178480900, compound

HRID 415117Notes

Reaction equation

HRID 415117 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([NH2:18])[C:14]([NH2:17])=[CH:15][CH:16]=2)[CH2:4][CH2:3]1.O.[N:20]#[C:21]Br>C(O)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]3[NH:17][C:21]([NH2:20])=[N:18][C:13]=3[CH:12]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 59349597HCID 59349597, compound

Product 1

HCID 178480900HCID 178480900, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 100 mL flasked was charged with 4-(2-(4-methylpiperazin-1-yl)ethoxy)benzene-1,2-diamine (4.35 mmol), water (50 mL) and acetic acid (2 mL) and stirred at room temperature for 15 minutes. The reaction mixture was placed in an ice bath and then charged with cyanogen bromide (0.526 g, 5 mmol). The reaction mixture was allowed to warm to room temperature and stirred over night. The reaction mixture was concentrated under reduced pressure and redissolved in acetone, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give 1.79 g of 5-(2-(4-methylpiperazin-1-yl)ethoxy)-1H-benzo[d]imidazol-2-amine. This material was used without any further purification. MS (EI): 276 (MH+).

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. temperatureto warm to room temperature
  3. stirringstirred over night
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionredissolved in acetone
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4051a91d7544706ba6901a878238825
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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