Water → HCID 178452335, compound

HRID 415114Notes

Reaction equation

HRID 415114 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[NH2:24])[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.O.[Br].[N:27]#[C:28]C#N>C(O)(=O)C>[NH2:27][C:28]1[NH:24][C:23]2[CH:22]=[CH:21][C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 59349631Tert-butyl 4-(2-(3,4-diaminophenoxy)ethyl)piperazine-1-carboxylateHCID 178511328HCID 178511328, compound

Product 1

HCID 178452335HCID 178452335, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 100 mL flasked was charged of tert-butyl 4-(2-(3,4-diaminophenoxy)ethyl)piperazine-1-carboxylate (1.53 g, 4.54 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 bromine (0.526 g, 5 mmol) and continued to stir at 0° C. The reaction temperature was allowed to warm to room temperature and it was stirred over night. The reaction was completed as determined by LCMS. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in acetone, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.7 g of tert-butyl 4-(2-(2-amino-1H-benzo[d]imidazol-5-yloxy)ethyl)piperazine-1-carboxylate as a di-acetate salt as black foam. MS (EI): 362 (MH+).

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. stirringto stir at 0° C
  3. temperatureto warm to room temperature
  4. stirringit was stirred over night
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe resulting residue was dissolved in acetone
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d0743eb5ae45404784a4f3cef54eb5f3
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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