Sodium Carbonate → HCID 59326836, compound

Participants

Reaction Steps

To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (109 mg, 0.450 mmol), NMP (2 mL) and 1-(3-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone (50 mg, 0.225 mmol) was added cesium carbonate (147 mg, 0.450 mmol). The reaction mixture was stirred and heated in a Biotage Initiator at 160° C. for 60 minutes. LC-MS shows complete conversion. The reaction was filtered through a Acrodisc syringe filter 0.2 mm ultipor nylon membrane. The filtrate was purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini column (5 micron, C18, 110 Å, Axia, 100×50 mm) eluting at 90 mL/min with an linear gradient of 10% to 80% MeCN (0.1% TFA) in water (0.1% TFA) over 20 minutes to give the product as a TFA salt. The desired fractions were poured into 10% Na2CO3 (aq)/DCM, and the DCM layer separated, dried over MgSO4, and concentrated in vacuo to give a mixture of (S)-1-(3-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)piperidin-1-yl)ethanone (13.5 mg, 0.030 mmol, 27.0% yield) and (R)-1-(3-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)piperidin-1-yl)ethanone (13.5 mg, 0.030 mmol) as a off white solid. MS (ESI, pos. ion) m/z: 445.1 (M+1). IC50 (uM) +++++.

Provenance & Evidence