Methanesulfonyl chloride → HCID 58529307, compound

Participants

Reaction Steps

To a solution 5-(2-benzyl-2H-indazol-6-yl)-7-(morpholin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (80 mg, 0182 mmol) in DMF (1.5 mL) was added methanesulfonyl chloride (15 μL, 0.20 mmol) and N,N-diisopropylethylamine (95 μL, 0.55 mmol). The reaction was stirred at rt for 17 h. The crude mixture was purified by preparative HPLC using a gradient elution from 15% to 45% acetonitrile in water followed by filtration through an acidic resin, washing with MeOH. The product was eluted with 2M NH3 in MeOH and the filtrate was concentrated to provide 20 mg (21%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.91 (s, 1 H), 7.80 (d, 1 H), 7.59 (s, 1 H), 7.26-7.41 (m, 5 H), 7.14 (d, 1 H), 6.68 (s, 1 H), 5.74 (s, 1 H), 5.65 (s, 2 H), 3.86-3.95 (m, 2 H), 3.51 (t, 1 H), 3.40 (d, 1 H), 3.04-3.17 (m, 2 H), 2.88 (s, 3H), 2.78-2.88 (m, 1 H), 2.62-2.71 (m, 1 H); ES-MS m/z 518.40 [M+H]+, HPLC RT (min) 2.51.

Provenance & Evidence