Tetrahydrofuran → 4-amino-5-(4-nitrophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

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Reaction Steps

A solution 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (495 mg, 1.73 mmol) in thionyl chloride (15 mL) was heated (50° C.) for 3 h. Upon cooling to rt the reaction mixture was concentrated to dryness. The resulting acid chloride intermediate was combined with 2,2,2-trifluoro-ethylamine hydrochloride salt (587 mg, 4.33 mmol), triethylamine (1.15 ml, 8.66 mmol), and THF (8 mL). The reaction was stirred for 16 h and then concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and then washed with water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was tritureated with ethyl acetate and methanol to afford the desired product (490 mg, 74%). 1H-NMR (300 MHz, DMSO-d6) 8.77 (t, J=6.2 Hz, 1H), 8.29 (s, 1H), 8.23 (d, J=8.9 Hz, 2H), 7.97 (s, 1. H), 7.59 (d, J=8.9 Hz, 2H), 3.91-3.99 (m, 2H); ES-MS m/z 381.1 (MH)+; HPLC RT (Method B) 2.33 min.

Provenance & Evidence