Reference of 6320-39-4 , The common heterocyclic compound, 6320-39-4, name is 3-Amino-4-hydroxypyridine, molecular formula is C5H6N2O, 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.
Step 1 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (100 mg, 0.24 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by the addition of 3-amino-4-hydroxypyridine (32.12 mg, 0.29 mmol) and potassium carbonate (67.19 mg, 0.49 mmol), then stirred at 60 C. overnight. After the reaction was completed, the reaction solution was diluted with water and then extracted with dichloromethane. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and separated by a preparative plate (Develop: EtOAc_MeOH=10:1) to give 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine 339 (30 mg, yield: 28.01%). MS m/z (ESI): 441.2 [M+1] 1H NMR (400 MHz, CDCl3) 8.16 (s, 1H), 8.00 (s, 1H), 6.76 (s, 1H), 4.91 (s, 1H), 4.61-4.59 (m, 2H), 4.18 (s, 1H), 4.04-4.01 (m, 2H), 3.55-3.48 (m, 2H), 2.44 (d, J=12.0 Hz, 1H), 2.33-2.23 (m, 1H), 2.08-1.43 (m, 16H), 1.37 (s, 3H), 1.25-1.15 (m, 3H), 0.79 (s, 3H).
The synthetic route of 6320-39-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem