Reaktion #165848

Reaktionsgleichung

TBTU

tert-butyl N-[[4-(hydrazinecarbonyl)phenyl]methyl]-N-methyl-carbamate

2-amino-5-bromo-pyridine-3-carboxylic acid

triethylamine

→

product

Ausbeute 99.7%

tert-butyl 4-(2-(3-amino-6-bromopyrazine-2-carbonyl)hydrazinecarbonyl)benzyl(methyl)carbamate

Ausbeute 99.7%

Lösungsmittel

ethyl acetate

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   ExtraktionThe aqueous layer was extracted further with ethyl acetate (2×20 mL)
3. 3
   Waschencombined organic extracts washed with saturated aqueous sodium hydrogen carbonate solution (1×20 mL), brine (1×20 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was triturated with CH2Cl2

Vorschrift

To a solution of tert-butyl N-[[4-(hydrazinecarbonyl)phenyl]methyl]-N-methyl-carbamate (1 g, 3.580 mmol) in DMF (7.769 mL) and 2-amino-5-bromo-pyridine-3-carboxylic acid (776.9 mg, 3.580 mmol) was added triethylamine (724.5 mg, 997.9 μL, 7.160 mmol) followed by TBTU (1.724 g, 5.370 mmol). The resulting mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with ethyl acetate (20 mL) and water (20 mL) and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×20 mL) and combined organic extracts washed with saturated aqueous sodium hydrogen carbonate solution (1×20 mL), brine (1×20 mL), dried over MgSO4 and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the product as a white solid (1.71 g, 58% yield); 1H NMR (400.0 MHz, DMSO) d 1.39-1.45 (m, 9H), 2.80 (s, 3H), 4.45 (s, 2H), 4.45 (s, 2H), 7.28 (s, 2H), 7.35 (d, 2H), 7.90 (d, 2H), 8.20 (d, 2H), 8.24 (d, 1H), 10.50 (s, 1H) and 10.54 (s, 1H) ppm; MS (ES+) 480.16

Quelle