Application of 59528-27-7, These common heterocyclic compound, 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, 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 mixture of (4-iodophenyl)methanamine hydrochloride (2.64 g, 9.80 mmol, 1.0 eq), (lS,2S)- Nl,N2- dimethylcyclohexane-l, 2-diamine (0.31 mL 1.96 mmol, 0.2 eq), Sodium ascorbate (198 mg, 0.98 mmol, 0.1 eq), Copper Iodide (279 mg, 1.47 mmol, 0.15 eq), Sodium azide (1.27 g, 19.59 mmol, 2.0 eq) , Et3N (1.64 mL, 11.75 mmol, 1.2 eq) and 3-(prop-2-yn-l-yloxy)oxetane (9, 1.10 g, 9.80 mmol, 1.0 eq) in Methanol (24 mL) and water (6 mL) were purged with Nitrogen for 5 minutes and heated to 55 C for over night. The reaction mixture was cooled to room temperature and filtered through a plug of Celite and rinsed with Methanol (3 x 50 mL). Celite was added to the filtrate and the solvent was removed under reduced pressure. The residue was purified over silica gel (120 g) using dichloromethane/(methanol containing 12 % (v/v) aqueous ammonium hydroxide) as mobile phase. The concentration of (methanol containing 12 % (v/v) aqueous ammonium hydroxide) was gradually increased from 0 % to 25 % to afford (4-(4- ((oxctan-3-yloxy)mcthyl)-l //-l ,2,3-triazol- 1 -yl)phcnyl)mcthanaminc (32, 1.43 g, 56%) as an oil. LCMS m/z: [M + H]+ Calcd for C13H16N4O2 261.1346; Lound 261.1342.
The synthetic route of 59528-27-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SIGILON THERAPEUTICS, INC.; MILLER, Robert, James; BARNEY, Lauren, Emily; JOHNSTON, Erika, Ellen; HEIDEBRECHT, Richard; BEAUREGARD, Michael; VEISEH, Omid; CARMONA, Guillaume; GONZALEZ, Francisco, Caballero; OBERLI, Matthias, Alexander; PERITT, David; SMITH, Devyn, Mckinley; WOTTON, Paul, Kevin; O’CONNOR, Owen; SEWELL, Jared, A.; (204 pag.)WO2019/195055; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com