Diethyl Ether → HCID 86664047, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-(dimethoxymethyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylate (35 mg, 0.063 mmol) was dissolved in DCM (2 mL), cooled to 0° C. and treated sequentially with Et3SiH (50 μL, 0.313 mmol) and BF3:OEt2 (15 μL, 0.119 mmol) and the mixture stirred for 10 mins then allowed to warm to rt. After 40 mins additional Et3SiH (50 μL, 0.313 mmol) was added at rt followed by BF3:OEt2 (15 μL, 0.119 mmol) and the mixture stirred for 2.5 h after which time the reaction was diluted with sat. NaHCO3 (aq), extracted with DCM (3×), dried and the solvent evaporated to yield the crude product (31.7 mg). The crude product was purified on 12 g SiO2 using EtOAc/Cyclohexane gradient 0-0% 3CV, 0-100% 30CV, 100-100% 5CV to yield the desired compound (22.3 mg, 73%). 1H NMR (CDCl3) δ 8.59 (s, 2H), 7.79 (d, J=1.2 Hz, 1H), 7.25 (d, J=0.9 Hz, 1H), 4.66 (s, 2H), 4.53 (dt, J=13.7, 3.5 Hz, 2H), 4.22 (q, J=7.1 Hz, 2H), 3.51-3.40 (m, 2H), 3.38 (s, 3H), 3.22-3.07 (m, 2H), 2.23 (d, J=13.4 Hz, 2H), 1.59 (q, J=7.5 Hz, 2H), 1.48-1.43 (m, 2H), 1.29 (dd, J=10.0, 4.1 Hz, 6H), 0.85 (t, J=7.5 Hz, 3H). MS: 527.15 [M+H]+

Provenance & Evidence