Synthetic Route of 76093-33-9 ,Some common heterocyclic compound, 76093-33-9, molecular formula is C16H16N2O6, 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.
To a solution of (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (4.86g, 14.6mmol) in dichloromethane was added 0.1mL DMF. To the mixture was slowly added oxalyl chloride (3.68g, 29.0mmol) dropwisely in an ice bath. The reaction was conducted at 25C until the completion of reaction. The resulting mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (20mL), the crude product of 1-(3,5-difluorobenzyl)-3-methylpyrrolidin-3-ol (1.8g) and DIPEA (1.86g, 14.4mmol) dropwisely under cooling in an ice bath respectively and successively. The reaction was conducted at 25C. After the completion of reaction monitored by HPLC, the reaction solution was washed with water thrice. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness, and purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate = 85:1 (volumetric ratio)) to produce (4S)-3-[1-(3,5-difluorobenzyl)-3-methyl-3-pyrrolidin-3-yl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (1.78 g) in a yield of 45.6% (two steps together). Molecular formula: C28H29F2N3O6 Mw: 541.2 MS (M+H): 543.3 1H-NMR(DMSO, 400 MHz) delta: 9.14 (1 H, t), 8.02-7.97 (2 H, m), 7.60-7.55 (2 H, m), 7.39-7.33 (2 H, m), 4.93-4.90 (1 H, d), 4.41-4.40 (2 H, m), 3.56-3.53 (6 H, m), 3.35 (1 H, s), 3.07 (1 H, s), 2.30-2.26 (6 H, m), 1.50-1.24 (3 H, dd), 1.10 (3 H, s).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 76093-33-9, (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem