Water → HCID 178476553, compound

HRID 415123Notes

Reaction equation

HRID 415123 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:4][CH2:3]1.[OH2:20].[N:21]#[C:22]Br>C(O)(=O)C>[C:12]([OH:20])(=[O:11])[CH3:13].[C:10]([OH:11])(=[O:20])[CH3:9].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]3[NH:18][C:22]([NH2:21])=[N:19][C:14]=3[CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 59349505HCID 59349505, compound

Product 1

HCID 178476553HCID 178476553, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 100 mL flasked was charged with 4-(3-(4-methylpiperazin-1-yl)propoxy)benzene-1,2-diamine (1.15 g, 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, and then filtered. The filtrate was concentrated under reduced pressure to give 1.7 g of 5-(3-(4-methylpiperazin-1-yl)propoxy)-1H-benzo[d]imidazol-2-amine diacetate. This material was used without any further purification. MS (EI): 290 (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-8349770d12d14de29e2ced74af3b71c4
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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