Synthetic Route of 4320-91-6, A common heterocyclic compound, 4320-91-6, name is 2H-1,2,3-Triazole-2-acetic acid, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A flask was charged with (2S,4S)-N-(4-(4- fluorophenoxy)phenyl)-4-(thien-2-ylmethyl)pyrrolidine-2-carboxamide (84 mg, 0.21 mmol), 2-(2H-l,2,3-triazol-2-yl)acetic acid (29 mg, 0.23 mmol), DIEA (0.5 mL, 2.9 mmol), HATU (81 mg, 0.21 mmol) and DMF (3 mL). The reaction mixture was stirred at ambient temperature for 20 minutes and quenched with saturated sodium bicarbonate (aq., 10 mL). The mixture was extracted with ethyl acetate (20 mL) and the extract was washed with deionized water (10 mL) and then brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Product was purified from the residue by reverse phase HPLC to give Compound 64, (2S,4S)- 1 -(2-(2H- 1,2,3- triazol-2-yl)acetyl)-N-4-(4-fluorophenoxy)phenyl)-4-(thien-2-ylmethyl)pyrrolidine- 2-carboxamide (6.1 mg, 0.012 mmol, 6% yield), as an off-white solid. 1H-NMR (400MHz, CDCl3): 9.15 (s, IH), 7.72 (s, 2H), 7.44 (d, J = 8.8 Hz, 2H), 7.18-7.16 (m, IH), 7.03-6.82 (m, 8H), 5.29 (s, 2H), 4.86 (d, J = 8.0 Hz), 3.63-3.58 (m, IH), 3.25- 3.20 (m, IH), 3.12 (dd, J = 13.6, 4.8 Hz, IH), 3.01-2.87 (m, 2H), 2.73 (dd, J = 12.4, 5.2 Hz, IH), 1.75-1.68 (m, IH). MS (EI) for C26H24FN5O3S, found 506.2 (MH+).
The synthetic route of 4320-91-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; EXELIXIS, INC.; IBRAHIM, Mohamed, Abdulkader; JEONG, Joon, Won; JOHNSON, Henry William, Beecroft; KEARNEY, Patrick; LEAHY, James, W.; LEWIS, Gary, L.; NOGUCHI, Robin, Tammie; NUSS, John, M.; WO2010/45580; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics