Reaktion #168650

Reaktionsgleichung

HCl

cyclopropyl magnesium bromide

cyclopropyl magnesium bromide

3-amino-6-[3-(2-methoxy-ethylsulfamoyl)-phenyl]-pyrazine-2-carboxylic acid methoxy-methyl-amide

→

title compound

3-(5-Amino-6-cyclopropanecarbonyl-pyrazin-2-yl)-N-(2-methoxy-ethyl)-benzenesulfonamide

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Extraktionthe product extracted into EtOAc (120 ml)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane)

Vorschrift

A 1M solution of cyclopropyl magnesium bromide in THF (1.3 ml, 1.3 mmol) is added to a solution of 3-amino-6-[3-(2-methoxy-ethylsulfamoyl)-phenyl]-pyrazine-2-carboxylic acid methoxy-methyl-amide (Intermediate CB) (0.49 g, 1.24 mmol) in anhydrous THF (15 ml) under N2. The orange solution is stirred at room temperature for 18 hours after which time a 1M solution of cyclopropyl magnesium bromide in THF (1.3 ml, 1.3 mmol) is added. The orange solution is stirred at room temperature for 1 hour. 1M HCl (45 ml) is added and the product extracted into EtOAc (120 ml), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane) yields the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-6) δ 9.08 (1H, s), 8.51 (1H, m), 8.39 (1H, d), 8.22-7.90 (2H, br), 7.88 (2H, m), 7.76 (1H, t), 3.73 (1H, m) 3.37 (2H, t), 3.21 (3H, s), 3.02 (2H, q), 1.19 (2H, m), 1.14 (2H, m); MS m/z 377 [M+H]+

Quelle