4-methoxythiophene-3-carboxylic acid → HCID 44540247, compound

Participants

Reaction Steps

4-(Methyloxy)-3-thiophenecarboxylic acid (35 mg) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (84 mg) in DMF (250 μl) and DIPEA (69 μl). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (25 mg) in DMF (250 μl). The reaction mixture was left to stand at 22° C. for 18 h. The solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 ml) prior to application on to an aminopropyl SPE cartridge (0.5 g) that had been preconditioned with methanol and then chloroform. The product was eluted after 2 hr with ethyl acetate/methanol (1:1, 3 ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) gave the title compound.

Provenance & Evidence