Dimethylformamide → HCID 86664045, compound

Participants

Reaction Steps

1.4M BuLi (600 μL, 0.84 mmol) was added to ethyl 1-[5-[7-bromo-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylate (250 mg, 0.41 mmol) in THF (10 mL) at −90° C. and the reaction stirred for 10 mins before DMF (300 μL) was added and the mixture stirred for a further 20 mins. The reaction was quenched with sat. NH4Cl (aq) then allowed to warm to rt before extraction with EtOAc (3×). Combined EtOAc extracts were dried and the solvent evaporated to yield the crude product which was purified by flash chromatography on 12 g SiO2 using EtOAc/Cyclohexane gradient 0-0% 3CV, 0-100% 20CV, 100-100% 5CV to yield the desired product (105 mg, 46%). 1H NMR (CDCl3) δ 10.22 (s, 1H), 8.63 (s, 2H), 8.06 (d, J=1.7 Hz, 1H), 7.83 (d, J=1.7 Hz, 1H), 5.21 (s, 2H), 4.56 (dt, J=13.8, 3.5 Hz, 2H), 4.33 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.51 (q, J=7.2 Hz, 2H), 3.23-3.13 (m, 2H), 2.67 (s, 3H), 2.25 (bd, J=13.4 Hz, 2H), 1.61 (q, J=7.6 Hz, 2H), 1.45 (ddd, J=13.5, 11.9, 4.2 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H), 1.25 (t, J=7.2 Hz, 3H), 0.86 (t, J=7.5 Hz, 3H).

Provenance & Evidence