As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 571188-59-5
Toluene (432.0 mL) and 4-(6-amino-pyridine-3-yl)-piperazine-l -carboxylic acid tert-butyl ester (34.3g, 0.123 moles) were charged into 2L 4N RB flask under nitrogen atmosphere at 30¡À5C and stirred for 5-10 min to get brown colored suspension. Reaction mass was cooled to 0¡À5C. Lithium hexamethyldisilazane 1M solution in THF (259.0 mL, 0.258 moles) was added dropwise to the reaction mass through addition funnel by maintaining the reaction mass temperature at 0 ¡À5C. And stirred the reaction mass for 10-15 min at 0 ¡À 5Cto get clear brown colored solution. Add the solution of 2-chloro-7-cyclopentyl-N,N-dimethyl-pyrrolo[2,3-d]pyrimidine- 6-carboxamide (36.0g, 0.123 moles) in 324.0 mL of toluene dropwise to the reaction mass through addition funnel at 0 ¡À5C. Reaction mass temperature was raised to 25- 35C and stirred for lh for reaction completion. (0107) After completion of reaction (by TLC), solvent was distilled off on rotavapor under vacuum at 55-60C to get the brown colored solid. DM water (360.0 mL) and aq. sodium bicarbonate solution (36.0g of sodium bicarbonate was dissolved in 720.0 mL of DM water) were added to the above solid and stirred for 10-15 min. Then methylene chloride (720 mL) was charged to the above solution and stirred for 5-l0min. Layers were separated. Organic layer washed with DM water (720 mL) and layers Separated. Solvent was distilled off from organic layer completely under vacuum at 45-50C on rotavapor to obtain brown colored solid. The solid was leached with methanol (180 mL) at 30 ¡À 5C to afford title compound as pale brown colour solid. Weight of the product: 57.0g (86.6% by theory). Purity by HPLC > 98.0%. (0108) H1 NMR (DMSO-d6): d 9.412 (S, 1 H), 8.167-8.190 (d, 2 H), 8.02-8.03 (d, 1 H), 7.449-7.479 (dd, 1 H), 6.603 (S, 1 H), 4.690-4.778 (m, 1 H), 3.472-3.484 (d, 4 H), 3.062-3.073 (d, 10H), 2.413-2.465 (m, 12 H), 1.92-1.991 (m, 4 H), 1.427-1.65 (m, 10H); Mass m/z (M+l): 535.25
The chemical industry reduces the impact on the environment during synthesis 571188-59-5, I believe this compound will play a more active role in future production and life.
Reference:
Patent; NATCO PHARMA LIMITED; ARUNKUMAR, Thiriveedhi; SWAPNA, Kondaveeti; SATHISH, Thumati; NARESH, Ghanta; JANAKI RAMA RAO, Ravi; DURGA PRASAD, Konakanchi; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; (36 pag.)WO2019/142206; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem