Reaktion #172599

Reaktionsgleichung

6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone

1-hydroxy-7-azabenzotriazole

EDC

N-methylmorpholine

→

title compound

Ausbeute 87.4%

6-Bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide

Ausbeute 87.4%

Lösungsmittel

dimethyl sulfoxide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 10 min
2. 2
   workup.WAITto sit for 20 min
3. 3
   FiltrationThe suspension was filtered
4. 4
   WaschenThe collected solid was washed with about 50 mL of water
5. 5
   Filtrationfiltered
6. 6
   Sonstigeair dried for 15 min
7. 7
   Sonstigethen dried in vac oven

Vorschrift

To a mixture of 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (0.52 g, 1.837 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.485 g, 2.57 mmol), 1-hydroxy-7-azabenzotriazole (0.375 g, 2.76 mmol) and EDC (0.528 g, 2.76 mmol) in dimethyl sulfoxide (15 mL) was added N-methylmorpholine (0.606 mL, 5.51 mmol) via syringe. The reaction was stirred at RT for 48 h. The contents were slowly diluted into 200 mL of water, stirred for 10 min, then allowed to sit for 20 min. The suspension was filtered. The collected solid was washed with about 50 mL of water, filtered, air dried for 15 min then dried in vac oven to afford the title compound (0.67 g, 85%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) ppm 1.45 (d, J=6.57 Hz, 6H) 2.12 (s, 3H) 2.20 (s, 3H) 4.33 (d, J=5.05 Hz, 2H) 5.05 (quin, J=6.57 Hz, 1H) 5.89 (s, 1H) 7.71 (d, J=1.26 Hz, 1H) 8.20 (s, 1H) 8.37 (s, 1H) 8.62 (t, J=4.67 Hz, 1H) 11.54 (s, 1H). MS(ES) [M+H]+ 417.1.

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