N,N-Dimethylglycine → HCID 71134321, compound

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Reaction Steps

A mixture of 5-(2-benzyl-2H-indazol-6-yl)-7-(2-piperidin-4-yl-1,3-thiazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine hydrochloride (100 mg, 0.17 mmol), N,N-dimethylglycine (19 mg, 0.18 mmol), EDCl (36 mg, 0.19 mmol), HOBt (26 mg, 0.19 mmol), and N,N-diisopropylethylamine (90 μL, 0.52 mmol) in DMF (1.5 mL) was stirred at rt for 16 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 (20%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1 H), 8.37 (s, 1 H), 8.09 (s, 1 H), 7.82 (d, 1 H), 7.67 (s, 1 H), 7.26-7.39 (m, 5H), 7.16-7.23 (m, 2 H), 5.66 (s, 2 H), 4.40 (d, 1 H), 4.10 (d, 1 H), 3.01-3.23 (m, 3 H), 2.75 (t, 1 H), 2.18 (s, 6H), 2.06-2.15 (m, 3 H), 1.70 (q, 1 H), 1.53 (q, 1 H); ES-MS m/z 592.16 HPLC RT (min) 2.39.

Provenance & Evidence