Acetonitrile → HCID 86609634, compound

Participants

Reaction Steps

Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (204 mL, 4.20 mmol) were added to 1-(5-nitro-1-benzofuran-7-yl)octahydrothieno[3,4-b]pyrazine 6,6-dioxide (0.354 g, 1.05 mmol; Intermediate 35) in a mixture of THF (20 mL) and EtOH (80 mL). The resulting mixture was stirred at room temperature overnight and then more Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (204 mL, 4.20 mmol) were added and stirring was continued overnight. The mixture was filtered through Celite and the solvent was removed in vacuo to afford 0.338 g (quantitative). HPLC 90%, RT: 0.782 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 2.79 (dd, J=12.49, 7.30 Hz, 1H) 2.90-3.25 (m, 4H) 3.43-3.64 (m, 3H) 3.91-3.94 (m, 1H) 5.01-5.07 (m, 1H) 6.33 (d, J=1.98 Hz, 1H) 6.61 (dd, J=12.99, 2.10 Hz, 2H) 7.62 (d, J=1.98 Hz, 1H). LC-MS 308 (M+H)+.

Provenance & Evidence