With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.
To a solution of (4S)-5-(pyridin-2-ylcarbamoyl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine-7-carboxylic acid (250 mg, 0.768 mmol) in N,N-Dimethylformamide (DMF) (5 mL) under nitrogen at room temp, HATU (584 mg, 1.537 mmol), DIPEA (0.268 mL, 1.537 mmol) and tetrahydrofuran-3-amine (100 mg, 1.153 mmol) were added and the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with ice water and extracted with 2¡Á15 ml of ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulfate and concentrated under reduced pressure to afford crude compound. The crude product was purified by flash column chromatography (100-200 silica gel eluted with 2percent of CH2Cl2/MeOH) to afford (4S)?N5-(pyridin-2-yl)-N7-(tetrahydrofuran-3-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5,7(2H)-dicarboxamide (140 mg, 0.353 mmol, 45.9percent yield) as off white solid. (TLC system: 10percent Methanol in DCM. Rf value: 0.35), LCMS (m/z): 395.23 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta ppm 13.01 (s, 1H), 8.30 (dd, J=4.93, 0.99 Hz, 1H), 7.98-8.17 (m, 2H), 7.93-7.77 (m, 1H), 7.74-7.60 (m, 2H), 7.13 (ddd, J=7.23, 4.93, 0.99 Hz, 1H), 5.48 (dd, J=5.70, 3.07 Hz, 1H), 4.75-4.44 (m, 1H), 4.05-3.55 (m, 4H), 3.23-2.81 (m, 4H), 2.37-2.15 (m, 2H), 2.16-2.05 (m, 1H), 2.16-1.78 (m, 1H).
The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem