Category: 88625-24-5

Electric Literature of 88625-24-5, A common heterocyclic compound, 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, molecular formula is C5H3ClN2O, 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.

3,3-Difluoropiperidine hydrochloride [CAS RN: 496807-97-7] (531 mg, 3.37 mmol,1.6 eq), 5-chloropyrazine-2-carbaldehyde [CAS RN: 88625-24-5] (300 mg,2.11 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.43 g, 6.74 mmol,3.2 eq) were suspended in 20 mL 1,2-dichloroethane. Then, triethylamine (0.59 mL, 4.21 mmol, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added. After stirring for 10 mm, the resulting phases were separated by the use of a Whatman filter. The volatile components of theorganic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 340 mg (58% yield of theory) of the title compound.UPLC-MS (Method 2): R = 1.09 mm; MS (EI0): m/z = 248 [M+H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 1.64 (m, 2H), 1.86 (m, 2H), 2.73 (t, 2H),3.78 (5, 2H), 8.49 (d, 1H), 8.74 (d, 1H), 2H?s obscured by solvent signal.

The synthetic route of 88625-24-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 88625-24-5,Some common heterocyclic compound, 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, molecular formula is C5H3ClN2O, 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.

tert-Butyl (1R,3r,5S)-3-[5-butylpyrazin-2-yl]oxy-8-azabicyclo[3.2.1]octane-8-carboxylate. Step 1. To a solution of n-propyl-triphenylphosphonium bromide (0.745 g, 1.1 eq., 1.94 mmol) in dry THF (168 mL) n-BuLi (2.5M in hexane) (0.785 mL, 1.1 eq., 1.94 mmol) was added dropwise at 0C. and the reaction mixture was stirred at the same temperature for 45 min. 5-Chloropyrazine-2-carbaldehyde (0.745 g, 1.1 eq., 1.94 mmol) was added and the crude mixture stirred at room temperature for 16 h, quenched with water (20 mL) and extracted with EtOAc (230 mL). The organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to furnish a crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (9:1) to give (E/Z)-2-(but-1-enyl)-5-chloro-pyrazine (90 mg, 30%), as a 1:2 cis/trans mixture of isomers.

The synthetic route of 88625-24-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, A new synthetic method of this compound is introduced below., Safety of 5-Chloropyrazine-2-carbaldehyde

To a solution of 5-chloropyrazine-2-carbaldehyde (500 mg, 3.51 mmol) in CH2CI2 (10 mL) was added (diethylamino)difluorosulfonium tetrafluoroborate (2.0 g, 8.77 mmol) and triethylamine trihydrofluoride (0.57 mL, 3.51 mmol). The reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was diluted with water and was extracted with CH2CI2. The organic layer was dried over anhydrous MgSO/t, filtered and concentrated under reduced pressure. Purification of the residue via column chromatography (Si(, heptane:ethyl acetate 0-65%) gave the title (200 mg, 1.22 mmol, 35% yield). JH NMR (500 MHz, DMSO- ) delta ppm 9.00 – 8.93 (m, 1H), 8.86 (q, J = 1.1 Hz, 1H), 7.17 (t, J = 54.0 Hz, 1H); MS (ESI+) m/z 186 (M+Na)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem