Thiophenol → HCID 136341338, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine (129 mg, 0.293 mmol) in NMP (3 mL) was added Na2CO3 (47 mg, 0.439 mmol) followed by PhSH (35 μL, 0.337 mmol). The resulting mixture was sealed, evacuated and back filled with nitrogen (×3), then heated at 190° C. for 20 minutes under microwave irradiation. The reaction mixture was diluted with MeOH (10 mL) and filtered through celite. The filtrate was acidified by addition of acetic acid (3 mL) and loaded onto a 2 g SCX cartridge (pre-wet with MeOH). The cartridge was washed with MeOH (15 mL) and flushed with 7M NH3 in MeOH (15 mL). The MeOH/NH3 was removed in vacuo to afford the crude product as a brown solid. The crude material was purified by UV-directed preparative HPLC under basic (5 mM NH4OH) conditions, collecting at 352 nm, to afford the title compound as a pale brown glass-like solid (0.096 g, 77% yield). LC-MS: Rt 0.88 min; MS m/z 427.2 [M+H]+ [Method A]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13 (s, 1H), 7.86-7.78 (m, 2H), 7.17-7.10 (m, 2H), 4.35-4.25 (m, 1H), 3.87 (s, 3H), 2.99 (s, 3H), 1.62 (dd, J=11.87, 3.28 Hz, 2H), 1.43 (t, J=12.13 Hz, 2H), 1.21 (s, 6H), 1.09 (s, 6H). LC-MS: Rt 1.69 min; MS m/z 427.4 [M+H]+ [Method B]. HR-MS: Rt 1.49 mins; MS m/z 427.2660 [M+H]+ [Method C].

Provenance & Evidence