Reaktion #1966338

Reaktionsgleichung

2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide

4-fluoro-N-methyl-benzylamine

diisopropylethylamine

dimethyl acetamide

→

2-{6-[(4-fluoro-benzyl)-methyl-amino]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide

Ausbeute 44.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was cooled to room temperature
2. 2
   Waschenwashed with water, brine
3. 3
   Trocknendried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 70:30, v/v] and recrystallization from ether/pentane

Vorschrift

Part C. To a sealed tube was added 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide (100 mg, 0.22 mmol, 1.0 equiv), 4-fluoro-N-methyl-benzylamine (58 μL, 0.44 mmol, 2.0 equiv), diisopropylethylamine (17 μL, 0.44 mmol, 2.0 equiv) and dimethyl acetamide (1 mL). The reaction mixture was stirred at 100° C. After 5 hr, the reaction mixture was cooled to room temperature and diluted with dichloromethane, washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 70:30, v/v] and recrystallization from ether/pentane to afford 2-{6-[(4-fluoro-benzyl)-methyl-amino]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide (45 mg, 44%). 1H NMR (400 MHz, CD2Cl2) δ 8.57 (s, 1H), 8.06 (s, 1H), 7.24-7.34 (m, 4H), 6.98-7.05 (m, 4H), 6.18 (bs, 1H), 4.80 (s, 2H), 4.54 (d, J=8.0 Hz, 2H), 3.13 (s, 3H), 2.70 (s, 3H); HRMS (M+H)+=466.15.

Quelle