Reaktion #811624

Reaktionsgleichung

3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid

cyclopropylamine

HATU

triethylamine

→

3-(1H-benzoimidazol-2-yl)-N-cyclopropyl-1H-indazole-6-carboxamide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenvia aqueous wash
2. 2
   Extraktionextraction with ethyl acetate (3×50 mL)
3. 3
   TrocknenThe organic layer was then dried with MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto yield a dark oil

Vorschrift

To 3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid (200 mg, 0.719 mmol) in DMF (30 mL) was added cyclopropylamine (98 mg, 0.719 mmol), HATU (0.719 mmol, 273 mg), and triethylamine (0.726 mmol, 0.1 mL). This solution was allowed to stir at room temperature overnight. The reaction was worked up via aqueous wash and extraction with ethyl acetate (3×50 mL). The organic layer was then dried with MgSO4, filtered and concentrated to yield a dark oil. Flash column chromatography (30–70% Ethyl Acetate/Petroleum Ether) afforded the 3-(1H-benzoimidazol-2-yl)-N-cyclopropyl-1H-indazole-6-carboxamide as a yellow solid. (0.130 g, 57%) 1H NMR (DMSO-d6) δ 13.88 (1H, s), 8.63 (1H, m), 8.51 (1H, d, J=8.5 Hz), 8.09 (1H, s), 7.75 (1H, d, J=8.7 Hz), 7.63 (2H, br s), 7.21 (2H, m), 2.89 (1H, m), 0.72 (2H, m), 0.63 (2H, m). MS (APCI positive) 318.1.

Quelle