Electric Literature of 423165-07-5,Some common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, 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.
To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C. N?-{2-Chlorophenyl)-[3-(3-isopropyl-5-methyl-[1,2,4]-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]methyl}hydrazinecarboxamide (4a): White solid, yield: 75.85 %, m.p. 230-232 C. IR (KBr, numax, cm-1): 3464, 3242, 3151, 3060, 2987,1722, 1654, 1591, 1510, 1415, 1344, 1278, 1219, 1157, 1093,1051, 1033, 918, 852, 736, 627. 1H NMR (DMSO-d6, 400 MHz):delta10.49 (s, 2H, -NH2, D2O exchangeable), 8.26 (s, 1H, chiralproton), 8.15-8.18 (m, 1H, Ar-H, J1= 6.023 Hz, J2= 3.51 Hz),7.47-7.49 (m, 1H, Ar-H, J1= 5.27 Hz, J2= 3.26 Hz, J= 7.027Hz),7.368-7.397 (m, 2H, Ar-H, J2= 3.514Hz, J2= 6.023 Hz),6.589 (br, s, 2H, -2NH), 3.789 (s, 3H,-CH3), 3.46 (m, 1H, Ha),3.31-3.36 (1H, m, J= 9.53 Hz), 2.668-2.677 (m, 2H, J= 1.757Hz), 2.326-2.335 (m, 2H, J= 1.757 Hz), 1.88-1.97 (m, 4H, J1= 1.225 Hz, J2= 2.008 Hz), 1.253-1.236 (d, 6H, 2 × CH3, J=7.027 Hz); 13C NMR: 8.1 (CH3), 24.4 (2 × CH3), 28.4 (2 ×CH2), 26.3 (1CH)-isopropyl), 31.8 (1CH), 36.6 (2 × CH2), 52.7(2 × CH), 65.2 (1CH, adjacent to arom. ring), 126.3, 128.4,128.6, 130.4, 136.7, 137.3 (6C-arom. ring), 158.8 (-C=O,amide), 163.7 (2C, imine (C=N)). Mass: m/z: 429 (M-2), 391((M-2)-isopropyl), 414 ((M-2)-NH3), 301, 309, 279.
The synthetic route of 423165-07-5 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics