Dimethylformamide → HCID 86664033, compound

Participants

Reaction Conditions

Reaction Steps

A medium pressure reaction vessel was charged with the following reagents and solvent(s): Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylate (2.54 g, 4.52 mmol), palladium acetate (102 mg, 0.452 mmol), Pd(dppf)Cl2.CH2Cl2 (200 mg, 0.2 mmol), 3-diphenylphosphanylpropyl(diphenyl)phosphane (200 mg, 0.5 mmol), triethylsilane (2.3 mL, 14 mmol), triethylamine (1.3 mL, 9.05 mmol) in DMF (35 mL). The mixture was pressurised to 100 psi of carbon monoxide and heated at 75° C. overnight. The reaction was filtered through a 0.4 micron filter, and the majority of the DMF was removed in vacuo. Partitioning the crude mixture between DCM (100 mL) and washing with water (100 mL) followed by sat. aq. brine (100 mL) afforded a dark red syrup upon drying over MgSO4 and removal of the volatiles. Subjecting the residue to flash chromatography (Grace 80 g, 0-10% DCM/MeOH) yielded 1.85 g (80% yield) of the product as a yellow solid. 1HNMR (CDCl3) δ 10.20 (d, J=12.8 Hz, 1H), 8.65 (d, J=9.9 Hz, 2H), 8.11 (d, J=1.6 Hz, 1H), 7.86 (d, J=1.7 Hz, 1H), 4.58 (dt, J=13.7, 3.4 Hz, 2H), 4.23 (qd, J=7.1, 3.4 Hz, 2H), 3.57-3.41 (m, 2H), 3.28-3.10 (m, 2H), 2.26 (d, J=13.2 Hz, 2H), 1.61 (dt, J=7.5, 5.7 Hz, 4H), 1.52-1.39 (m, 2H), 1.31 (td, J=7.2, 3.6 Hz, 6H), 0.91-0.84 (m, 3H). MS: 511.0 [M+H]+.

Provenance & Evidence