Synthetic Route of 59528-27-7,Some common heterocyclic compound, 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, molecular formula is C7H9ClIN, 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 (5.0 g, 18.55 mmol, 1.0 eq), (lS,2S)- Nl,N2- dimethylcyclohexane-l, 2-diamine (0.59 mL 3.71 mmol, 0.2 eq), Sodium ascorbate (368 mg, 1.86 mmol, 0.1 eq), Copper Iodide (530 mg, 2.78 mmol, 0.15 eq), Sodium azide (2.41 g, 37.1 mmol, 2.0 eq) , Et3N (3.11 mL, 22.26 mmol, 1.2 eq) and 2-(prop-2-yn-l-yloxy)tetrahydro- 2 /-pyran (2.6 g, 18.55 mmol, 1.0 eq) in Methanol (50 mL) and water (12 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 413 filter paper. Celite was added and the solvent was removed under reduced pressure and 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 6.25 % to afford (4-(4-(((tctrahydro-2/7-pyran-2- yljoxyjmcthyl)- 1 H- 1 ,2,3-triazol- 1 -yljphcnyljmcthanaminc (15, 3.54 g, 66%) as a white solid. LCMS m/z: [M + H]+ Calcd for C15H20N4O2 289.2; Found 289.2.
The synthetic route of 59528-27-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SIGILON THERAPEUTICS, INC.; SMITH, Devyn, McKinley; PERITT, David; VEISEH, Omid; HEIDEBRECHT, Richard; MILLER, Robert, James; (173 pag.)WO2019/195056; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com