2-chloro-N,N-dimethylacetamide → HCID 58529909, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(morpholin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (80 mg, 0.18 mmol) in MeOH (1.5 mL) was added 2-chloro-N,N-dimethylacetamide (24 mg, 0.20 mmol) and N,N-diisopropylethylamine (95 μL, 0.55 mmol). The reaction was stirred at 60° C. 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 49 mg (52%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.51-8.57 (m, 1H), 7.86-7.93 (m, 1 H), 7.76-7.84 (m, 1 H), 7.55-7.62 (m, 1 H), 7.26-7.41 (m, 5 H), 7.09-7.18 (m, 1 H), 6.58-6.66 (m, 1 H), 5.71-5.77 (m, 1 H), 5.62-5.68 (m, 2 H), 3.79-3.91 (m, 1 H), 3.68-3.79 (m, 1 H), 3.39-3.53 (m, 1 H), 2.90-3.20 (m, 7H), 2.69-2.82 (m, 4 H), 2.62 (d, 1 H), 2.11-2.24 (m, 1 H), 1.96-2.09 (m, 1 H); ES-MS m/z 525.38 [M+H]+, HPLC RT (min) 2.03.

Provenance & Evidence