Cyanogen Bromide → N2-[1-benzyl-2-(1-[(2-cyano-1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamide

HRID 339488Notes

Reaction equation

HRID 339488 reaction equation
[CH2:1]([CH:8]([NH:23][C:24]([C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1)=[O:25])[C:9]([NH:11][CH:12]([C:17]([N:19]([CH3:22])[NH:20][CH3:21])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[N:37]#[C:38]Br>CO>[CH2:1]([CH:8]([NH:23][C:24]([C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1)=[O:25])[C:9]([NH:11][CH:12]([C:17]([N:19]([CH3:22])[N:20]([C:38]#[N:37])[CH3:21])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 67326475N2-[1-benzyl-2-(1-[(1,2-dimethylhydrazino) carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamide

Product 1

HCID 86655086N2-[1-benzyl-2-(1-[(2-cyano-1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamideYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N2-[1-benzyl-2-(1-[(1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamide (100 mg, 0.23 mmol) and sodium acetate (53 mg, 0.64 mmol) were dissolved in methanol (1 mL). Cyanogen bromide (49 mg, 0.46 mmol) was added and the solution was stirred for 4 h. Methanol was concentrated by rotary evaporation. The pH value was adjusted (5% NaHSO3) to 1-2. The solution was extracted by EtOAc, and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, 1/1: Hexane/EtOAc, Rf=0.3) afforded N2-[1-benzyl-2-(1-[(2-cyano-1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamide as pale yellow solid (67 mg, 65%).

Workup

  1. concentrationMethanol was concentrated by rotary evaporation
  2. extractionThe solution was extracted by EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customPurification by chromatography (silica, 1/1: Hexane/EtOAc, Rf=0.3)

Sources & evidence

ORD record
ord-42bbe04e1bab4235b635b1af104f8142
Source dataset
uspto-grants-2014_11
Patent number
US08895497B2

Reaction notes

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