Trifluoroacetic acid → 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine-1-carboxylate (0.7 g, 2.0 mmol) was taken up in 20 mL of DCM and treated with 7 mL of TFA. The mixture stirred for 1 h and was then reduced in vacuo. The solids were transferred to a 50 mL sealed tube and taken up in 20 mL of dioxane. TEA (0.58 g, 5.75 mmol) was added followed by ethenyl methyl sulfone (0.51 g, 4.79 mmol). The mixture was heated to 30° C. for 24 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step B (0.7 g, 1.88 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 6.56 (s, 1H), 3.86 (s, 3H), 3.33-3.42 (m, 4H), 3.26 (t, J=6.68 Hz, 2H), 2.99 (s, 3H), 2.87 (t, J=6.59 Hz, 2H), 2.74-2.81 (m, 2H), 2.67-2.74 (m, 2H), 2.20 (s, 3H), 1.81-1.89 (m, 2H).

Provenance & Evidence