1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529901, compound

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Reaction Conditions

Reaction Steps

To a cooled (−20° C.) solution of 3-(4-amino-pyrrolo[2,1-f][1,2,4]triazine-7-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.19 g, 3.59 mmol) in tetrahydrofuran (35 mL) was added THF solution of 1,3-dibromo-5,5-dimethylhydantoin (0.56 g, 1.97 mmol). The mixture was allowed to stir (−20° C.) for 2 h and then allowed to warm to rt. The reaction was quenched with the addition of 10% aqueous Na2S2O3 solution. The mixture was extracted with ethyl acetate (3×75 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness. The crude material was purified by Biotage® chromatography using a gradient of 50% to 75% ethyl acetate in hexanes to afford 1.33 g (90%) of the desired product. 1H NMR (300 MHz, CD3OD-d4) δ 8.00 (s, 1 H), 7.45 (d, 1 H), 6.94 (d, 1 H), 4.44-4.32 (m, 1 H), 3.65-3.59 (m, 2 H), 3.47-3.38 (m, 2 H), 2.31-2.11 (m, 2 H), 1.45 (s, 9 H); LC-MS [M+H]+=411.7, RT=2.98 min.

Provenance & Evidence