Tag: M.W=100-200

Synthetic Route of 313339-92-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 313339-92-3 as follows.

A solution of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.862 mmol), (R)-2-amino-2-phenylacetamide hydrochloride (160 mg, 0.858 mmol) and DIEA (0.400 mL, 2.30 mmol) in DMF (5 mL) was stirred at room temperature for 6 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-2-phenylacetamide (245 mg).

According to the analysis of related databases, 313339-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 889447-19-2, These common heterocyclic compound, 889447-19-2, name is 2-Chloro-5H-pyrrolo[2,3-b]pyrazine, 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.

Example 33A 2-chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine A 1 M solution of iodine monochloride in dichloromethane (9.84 mL, 9.84 mmol) was added dropwise to an ice-cold solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (6.75 g, 11.07 mmol) in anhydrous pyridine (12 mL). The reaction mixture was stirred at 0 C. for 60 minutes, then concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The crude product was stirred with 15 mL of dichloromethane. The yellow solid material was collected by filtration, washed with dichloromethane and dried to give 2.86 g of the title product. Yield: 66%. MS (DCI+) m/z 280 (M+H)+.

Statistics shows that 2-Chloro-5H-pyrrolo[2,3-b]pyrazine is playing an increasingly important role. we look forward to future research findings about 889447-19-2.

Reference:
Patent; ABBOTT LABORATORIES; US2011/15172; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 19847-12-2,Some common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, molecular formula is C5H3N3, 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 pyrazine-2-carbonitrile 13 (6.90 g, 65.65 mmol) in toluene (48 mL) and DMF (5 mL) was added sulfuryl chloride (21.2 mL, 260.8 mmol) over 10 min. The reaction mixture was stirred for 30 min in an ice bath, then allowed to warm up to room temperature gradually, after which it was stirred for 5 h. The toluene layer was decanted, and the reddish oil residue was extracted three times with diethyl ether. The combined toluene and ether layers were quenched with ice water and cooled in an ice bath. The combined layers were then neutralized with solid NaHCO3, then separated, and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated under reduced pressure to afford the title compound. The crude product was purified by silica gel chromatography (eluent: 100% dichloromethane) to give 3-chloropyrazine-2-carbonitrile 14 as a white powder (4.7 g, 51%). Rf = 0.76 (dichloromethane); mp 44-46 C (lit. [14] : 47-48 C); IR (KBr) numax (cm-1): 3088 (nuCHar), 2242 (nuCN), 1377 (nuC=C), 1087 (nuC-N); 1H NMR (400 MHz, DMSO-d6): delta 8.91 (d, 1H, J = 2.4 Hz, H-6), 8.88 (d, 1H, J = 2.4 Hz, H-5); 13C NMR (100 MHz, DMSO-d6): delta 150.67 (C-3), 147.97 (C-5), 144.26 (C-6), 129.87 (C-2), 114.66 (CN); MS (ESI) m/z (%): 140.3 (100) [M + H]+, 142.3 (40) [M + H + 2]+. Anal. calcd for C5H2ClN3: C, 43.04; H, 1.44; N, 30.11. Found: C, 43.18; H, 1.45; N, 30.16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazinecarbonitrile, its application will become more common.

Reference:
Article; Loidreau, Yvonnick; Marchand, Pascal; Dubouilh-Benard, Carole; Nourrisson, Marie-Renee; Duflos, Muriel; Lozach, Olivier; Loaec, Nadege; Meijer, Laurent; Besson, Thierry; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 171 – 183;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

A 5 liter flange-neck flask equipped with an air stirrer rod and paddle,thennometer, water condenser and nitrogen bubbler is charged with sodium hydride (22.4 g, 560.1 mmol) and anhydrous THF (3 L). To the well stirred mixture is added 2-amino- 5-cyanopyrazine (67.0 g, 557.8 mmol) portion-wise over 1.5 hours while allowing for any foaming. The internal temperature remains at 22 C throughout. The mixture is stirred for 35 minutes. Then I -(2-methoxy-6-4-methoxy-benzyloxy)-phenyi)-3,3-bis-methyisulfanyl-propenone (146.0 g, 373.9 mmoi) is added at 22 C over one hour. The yellow suspension is stirred for 45 minutes at room temperature and then heating is applied until the reaction is at a gentle refiux. Afier 19 hours at 65 C the reaction mixture is cooled to 15 C. The mixture is then split in two halves and each lot is quenched into water (2 L) and extracted with ethyl acetate (2 x L). The organic extractsare combined and washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure at 40 C to give the title compound (196 g, 100% crude) as a yellow/orange solid which is used in the next step without further purification. LC-ES/MS mIz 463.2 [M¡ÂHf.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; STANCATO, Louis Frank; (58 pag.)WO2017/15124; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59489-39-3,Some common heterocyclic compound, 59489-39-3, name is 2-Amino-6-cyanopyrazine, molecular formula is C5H4N4, 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.

Intermediate 5 (500 mg, 1.13 mmol) , 6-aminopyrazine-2-carbonitrile (163 mg, 1.36 mmol) , palladium (II) acetate (84 mg, 0.374 mmol) , xantphos (215 mg, 0.374 mmol) and cesium carbonate (741 mg, 2.27 mmol) in 1, 4-dioxane (10 mL) under heating at 110 for 1 hour through microwave irradiation under N2 atmosphere. LC-MS: m/z 526.2 (M+H) +.

The synthetic route of 59489-39-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); 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

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 312736-49-5 as follows. Product Details of 312736-49-5

To a solution of 2-fluoro-4-trimethylsilanyl-phenylamine (3.8 g, 20.7 mmol,2.0 eq) in anhydrous THF (150 mL) at -78C under N2 was added dropwise a solution of 1.0 M LHMDS in THF (33.2 mL, 30 mmol, 3.2 eq) over 20 minutes. After 1 hour at -78C, a solution of 3,5-dichloro-pyrazine-2-carboxylic acid (2.0 g, 10.3 mmol) in anhydrous THF (30 mL) was added. The mixture was stirred at -78C for 30 minutes, and then stirred at ambient temperature for 18 hours. The mixture was quenched with water and the pH adjusted to pH 2 by the addition of 2 N HCl. The reaction mixture was extracted with ethyl acetate, and the organic layer washed with water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 20 to 50% ethyl acetate in hexane, followed by 0% to 30%, methanol in dichloromethane) to give the desired compound as a yellow solid (2.95 g, 83.8%). 1H NMR (CDCl3, 400MHz) delta ppm 10.41 (s, IH), 8.28 (t, J = 7.79 Hz, IH), 7.93 (s, IH), 7.40-7.23 (m, 2H), 0.27 (s, 9H).

According to the analysis of related databases, 312736-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/85983; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step B – Preparation of Compound Int-15b Int-15bTo a solution of (2R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (0.61 g, 4.36 mmol) in THF (8 mL) was added n-BuLi (2.5 M in hexane, 1.8 mL, 4.58 mmol) at -78 ¡ãC. After allowed to stir for 0.3 hours, Compound Int-15a (2.75 g, 6.98 mmol) in 2 mL of THF was added and the mixture was allowed to stir at the temperature for 4 hours. The reaction was quenched by saturated aqueous H4C1 solution and the organic layers were extracted with EtOAc. The combined organic solution was washed with brine solution, dried (Na2S04), and concentrated in vacuo. The residue obtained was purified using ISCO 40 g column (gradient from 0percent to 2.5percent ether in hexane) to provide Compound Int-15b, 783 mg (44percent). 1H MR (CDC13) delta 4.05 (m, 1H), 3.96 (t, J= 3.4 Hz, 1H), 3.72 (s, 3H), 3.71 (s, 3H), 3.49 (dd, 7= 2,8, 0.4 Hz, 1H), 3.26 (dd, 7= 6, 9.4 Hz, 1H), 2.30 (m, 1H), 1.96 (m, 1H), 1.60 (m, 2H), 1.37-1.17 (m, 3H), 1.08 (d, 7= 6.9 Hz, 3H), 0.99-0.86 (m, 2H), 0.72 (d, 7= 6.6 Hz, 3H), 0.49 (dd, 7= 11.0, 14.4 Hz, 1H), 0.35 (dd, 7= 11.0, 14.2 Hz, 1H), 0.16 (s, 6H).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DWYER, Michael P; KEERTIKAR, Kartik M; COBURN, Craig A; WU, Hao; HU, Bin; ZHONG, Bin; ZHANG, Chengren; DAN, Zhigang; WO2012/40924; (2012); 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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, A new synthetic method of this compound is introduced below., Computed Properties of C8H10N2O

General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31). L1: 2-Acetyl-3-ethylpyrazine-thiosemicarbazides; yield:79.6%. Anal. Calcd (%) for C9H13N5S: C, 48.41; H, 5.87; N, 31.36; S, 16.36. Found: C, 48.32; H, 5.80; N, 31.43; S, 16.40. IR, cm-1: 3430.8 (s, amide), 3234.7 (s, NH), 3158.7 (m, aromatic hydrogen), 1598.16, 1504.69, 1459 (s, aromatic), 1396.96 (m, C=N), 1293.39 (s, thioamide), 1155, 1102.57, 880 (m, C-H), 715 (m, C=S), 596. m/z (ESI): calcd for C9H13N5S, 222.08 [M-H]-. 1H NMR (400MHz, DMSO) delta 10.48 (s, 1H), 8.55 (d, J=2.4Hz, 1H), 8.49 (d, J=2.4Hz, 1H), 8.38 (s, 1H), 7.60 (s, 1H), 3.04 (q, J=7.4Hz, 2H), 2.35 (s, 3H), 1.20 (t, J=7.4Hz, 3H); 13C NMR (100MHz, DMSO) delta 179.42, 156.21, 150.18, 148.02, 142.99, 140.68, 28.00, 15.87, 12.75.

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:
Article; Khan, Muhammad Hamid; Cai, Meiling; Li, Shanhe; Zhang, Zhenlei; Zhang, Juzheng; Wen, Xiaoan; Sun, Hongbin; Liang, Hong; Yang, Feng; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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.

In 0 C lower, to the 5, 6, 7, 8-tetrahydro-imidazo [1, 5-a] pyrazine (50.0 mg, 0 . 40mmol) and Boc-(R)-3-amino-4-(2, 5-difluorophenyl) butanoic acid (128.0 mg, 0 . 40mmol) in dichloromethane (5 ml) is added in solution HOBT (54.5 mg, 0 . 42mmol). The reaction in the 0 C lower stirring 10 min, then adding EDC (96.6 mg, 0 . 50mmol). After removing the ice bath, the reaction stirring at ambient temperature 14h. The mixture is concentrated and used for purifying HPLC (Gilson; YMC-PackProC18 column, 100x20mmI. D. ; A solvent gradient from 10% acetonitrile, 90% water and 0.1% trifluoroacetic acid to 90% acetonitrile, 10% water and 0.1% trifluoroacetic acid), to obtain 103 mg in the form of a solid as the title compound.

Statistics shows that 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 297172-19-1.

Reference:
Patent; CGene Tech (Suzhou,China)Co.,Ltd; YU, QIANG; WEI, FENGPING; (31 pag.)CN101899047; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem