Cyclopentanethiol → HCID 178517608, compound

Participants

Reaction Steps

To a solution of cyclopentanethiol (54 μL, 0.50 mmol) in THF (0.5 mL) at 0° C. was added NaH (20.0 mg, 0.50 mmol). The reaction mixture was warmed to rt and tert-butyl 3-(methylsulfonyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate (100 mg, 0.25 mmol) was added, After 30 min, the reaction was quenched with aqueous NH4Cl and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (gradient elution, 0-100% EtOAc /hexanes) afforded the title compound. 1H NMR (400 MHz, ppm, CD3OD) δ 7.73 (d, J=2.3 Hz, 1 H); 6.50 (d, J=2.4 Hz, 1 H); 3.77 (m, 1 H); 3.44 (t, J=6.2 Hz, 2 H); 3.04 (t, J=6.3 Hz, 2 H); 2.32-2.22 (m, 2 H); 1.85-1.77 (m, 2 H); 1.76-1.65 (m, 4 H). HRMS (ES+) m/z 320.0879 [(M+H)+; calcd for C15 H17N3OS2: 320.0886].

Provenance & Evidence