Methanol → HCID 87222526, compound

Participants

Reaction Steps

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(methylaminomethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (130 mg, 0.25 mmol), N,N′-diisopropylethylamine (3.69 mmol, 477 mg, 324 ul) and 2-chloropyrimidine (1.75 mmol, 200 mg) were combined in isopropanol (2 mL) in a microwave tube equipped with a stirrer. The tube was purged with N2, sealed and irradiated to 110° C. for 1 hr in a CEM explorer microwave with stirring however LCMS indicated only starting material was present and the reaction was diluted with isopropanol (4 mL) and N,N′-diisopropylethylamine (4.19 mmol, 540 mg, 400 ul), then purged with N2, sealed then irradiated to 110° C. for 1 hr in the CEM explorer with stirring. LCMS indicated conversion to the desired product along with the corresponding isopropylester and starting material. The reaction was allowed to cool, the solvents removed under reduced pressure and the resulting residue partitioned between EtOAc and water and the layers separated. The aqueous portion was extracted with EtOAc and the combined organic portions dried (MgSO4) and concentrated to afford the crude product (160 mg). This material was purified by flash silica chromatography eluting with 0 to 50% EtOAc in petroleum-ether then 0 to 10% MeOH in DCM to afford the target material (40 mg, 27% yield).

Provenance & Evidence