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

HRID 339488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339488
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-42bbe04e1bab4235b635b1af104f8142
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895497B2

Notizen zur Reaktion

Wird geladen…