Month: March 2021

These common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, 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. COA of Formula: C10H15BrN4O2

EXAMPLE 176; 7- {5- [(6,7-dichloro- 1-oxo- 1 ,2-dihydr opyr rolo [1 ,2-alphal pyrazin-4-yl)methyll -2- fluorobenzoyl}-3-pyrrolidin- l-yl-5,6,7,8-tetr ahydro [ 1 ,2,41 triazolo [4,3-alphal pyrazin-2-ium trifluoroacetate (AA2)Step 1: 3-Pyrrolidin-l-yl-5,6,7,8-tetrahydro[l,2,41triazolo[4,3-alphalpyrazin-7-ium trifluoroacetate (AAl)A mixture of tert-bvXy 3-bromo-5,6-dihydro[l,2,4]triazolo[4,3-alpha]pyrazine-7(8H)-carboxylate(0.231 mmol) in pyrrolidine (3 ml) was stirred overnight in a sealed tube at 6O0C. The volatiles were removed under reduced pressure and the resulting crude was diluted with DCM and washed with sat. aq. NH4Cl solution. The organic phase was dried (Na2SO4) and filtered. Evaporation of the solvent provided a crude which was dissolved in a mixture of DCM/TFA (1:1, 0.23 M) and stirred at room temperature for 30 min. The volatiles were removed under reduced pressure and the resulting crude was used as such in the next step without purification. MS (ES) C9H15N5 required: 193, found: 194 (M+H)+.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/138355; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 123-32-0, 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. 123-32-0, name is 2,5-Dimethylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(b) 3,6-Dimethylpyrazin-2-amine[00426] A mixture of 2,5-dimethylpyrazine (14 g, 0.13 mol) in N,N-dimethylaniline (50 mL) was heated to 170 C and NaNH2 (22 g, 0.56 mol) was added in portions. The reaction mixture was stirred at 170 C for 1 h, and the solvent was removed. The product was purified by column chromatography to give 3,6-dimethylpyrazin-2-amine as a brown solid (1.6 g). MS (ESI): m/z 124[M+H]+.

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, 2,5-Dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emerson; HEWITT, Michael, Charles; JONES, Philip; XIE, Linghong; WO2011/150156; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 3149-28-8, The chemical industry reduces the impact on the environment during synthesis 3149-28-8, name is 2-Methoxypyrazine, I believe this compound will play a more active role in future production and life.

General procedure: Perfluorobutanesulfonyl azides 1a (715 mg, 2.2 mmol) and pyrazine 2a (2.0 mmol) was mixed without solvent at room temperature, this reaction mixture stirred for 8 h at 120 C, TLC analysis showed the reaction was completed. The product 3aa was obtained by flash column chromatography (using petroleum ether/ethyl acetate=2:1 as eluant) as a yellow solid in 34% yield (234 mg).

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, 2-Methoxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiong, Wanting; Zhang, Hongfei; Xin, Yong; Zhu, Shizheng; Tetrahedron; vol. 67; 12; (2011); p. 2232 – 2237;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 153800-11-4, 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. 153800-11-4 name is 2-Ethynylpyrazine, This 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.

To a solution of 18i(i00m, 03i9mmol) and 10(66.5mg, 0.639mmo1) in 2OmL of Et3N wasadded Pd(PPh3)2C12 (11.21mg, 0Oi6mmoi) and CuT (608mg, 0O32mmoi). The mixture wasprotected with N: atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-i-IPLC to give the target product Compound 111(18mg, yield: 1948%).LCMS: rn/z 290 (M¡ÀH) +?H NMR (400 MHz, CDCI3): 5 8.84 (d, J 1.6 Hz, 1H), 8.63-8.62 (rn, IH), 8.55 (d, J= 2.4 Hi, 111) 97 (d 1 2 S Hi III) 7 8 (t, 1H? 7 79 (d 1 9 2 hi ill) 4- 2 (in, 111), 6.83 (d, J:::: 2.4 Hz, IH),

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Ethynylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 937669-80-2, name is 3-Bromopyrazine-2-carboxylic acid, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 937669-80-2, COA of Formula: C5H3BrN2O2

In a 500 mL three-necked flask, 3-bromopyrazine-2-carboxylic acid (20.3 g, 0.1 mol) was dissolved in 200 ml of methanol, and 20 ml of concentrated sulfuric acid having a concentration of 98 wt% was added dropwise to the reaction solution.After stirring at room temperature for 12 hours, the reaction was quenched, the reaction was quenched with EtOAc (EtOAc)EtOAc.A mixed solvent of petroleum ether/dichloromethane (volume ratio of 2/1) was used as a rinse agent, and the yield was 83%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; South China Xietong Chuangxin Institute; Ying Lei; Hu Liwen; Huang Fei; Cao Yong; (22 pag.)CN108218891; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 313339-92-3,Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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.

2,3-Dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (5.78 g) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro-pyrazine-2-carbonitrile (2.35 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (Pd(dppf)2Cl2) (791 mg) and cesium carbonate (13.2 g), followed by 100 ml dioxane and 10 ml water, and the mixture heated to 100C under stirring. After 3 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (100 ml) and extracted with EtOAc (3 x 200 ml). The combined aqueous phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded 2,3-dichloro-N-[4-(6-chloro-5-cyano-pyrazin-2yl)-phenyl]-benzenesulfonamide as a light brown foam after evaporation of the solvents under reduced pressure. Yield: 4.32 g (73%). MS (ES-): m/e = 436.0 (M-H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloropyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; SANOFI; Nazare, Marc; Halland, Nis; Schmidt, Friedemann; Weiss, Thilo; Hofmeister, Armin; EP2570415; (2013); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-6-chloropyrazine

A solution of 2-amino-6-chloropyrazine (25 g, 193.1 mmol) in MeOH (500 mL) was treated with NBS (34.3 g, 193.1 mmol), portion-wise, over 1 hour. The resulting mixture was stirred for 16 hours thereafter. TLC analysis at this time shows a small amount of starting material remaining. Another 1.4 g NBS added and reaction heated to 50 C. for 2 hours. The mixture was then cooled to 38 C. and treated with NCS (25.8 g, 193.1 mmol). The reaction mixture was heated to 50 C. for 16 hours thereafter. The mixture was then cooled to room temperature and treated with water (500 mL). The precipitate was collected by filtration and dried in a vacuum dessicator to afford 45.4 g (97% yield) of 2-amino-5-bromo-3,6- dichloropyrazine as a white solid: 13C NMR (75 MHz, CDC13) delta 149.9 (s), 145.6 (s), 129.6 (s), 121.5 (s). LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=4.51 min on 30 mm column, (M+H)+=244, (M+H+ACN)+=285.

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIBEACON INC.; DORSHOW, Richard, B.; ROGERS, Thomas, E.; (90 pag.)WO2016/183351; (2016); 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 1458-01-1 as follows. HPLC of Formula: C6H7ClN4O2

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

According to the analysis of related databases, 1458-01-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 15707-23-0, name is 2-Ethyl-3-methylpyrazine, molecular formula is C7H10N2, 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. COA of Formula: C7H10N2

EXAMPLE II Preparation Of (R,S)-2-(2-Hydroxy-2-phenylethyl)-3-ethylpyrazine A reaction of 2-ethyl-3-methylpyrazine (12.2 g, 0.01 mole) with benzaldehyde (10.6 g, 0.1 mole) is conducted in accordance with the procedure of Example I. Workup followed by bulb-to-bulb distillation (155C oven/0.02 mm Hg) provides 18.2 g of a light yellow colored oil. This material crystallizes on trituration with hexane, giving 17.80 g (78%) of desired product, mp 52-53C. An analytical sample is obtained by recrystallization from hexane: mp 53-54C; 1H NMR (CDCl3) delta 1.25 (t, 3H, J = 7.4 Hz), 2.77 (q, 2H, J = 7.4 Hz), 3.16 (d, 2H, J = 6.2 Hz), 5.01 (d, 1H, J = 2.5 Hz), 5.28 (m, 1H), 7.27-7.46 (m, 5H), 8.33 (d, 1H, J = 2.8 Hz), 8.40 (d, 1H, J = 2.8 Hz). Anal. Calc. for C14H16N2O: C,73.65; H,7.06; N,12.27 Found: C,73.73; H,7.01; N,12.31

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15707-23-0, its application will become more common.

Reference:
Patent; Philip Morris Products Inc.; EP309203; (1990); A3;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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. category: Pyrazines

Preparation of (l^S^^^-methyl 3-amino-5-(5-(( )-2-(5-chloropyrazin-2-yl)-2- fluorovinyl)-2-fluorophenyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-l- carboxylate (Example 149). 1 ) A solution of 3-((tert-butoxycarbonyl)((2-(trimethylsilyl)ethoxy) methyl)amino)-5-(2-fluoro-5-((i-2-fluoro-2-(tributylstannyl)vinyl)phenyl)-5-methyl-2-thia- 4-azabicyclo[4.1.0]hept-3-ene-l-carboxylate (20B) (80 mg, 0.093 mmol) in 0.5 mL of DMF was added dropwise to a mixture of 2,5-dichloropyrazine (62.5 mg, 0.420 mmol), bis(di-fert- butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ii) (6.60 mg, 9.33 muiotaetaomicron) and copper(i) iodide (18 mg, 0.093 mmol) in 0.5 mL of DMF. After 1 hour, the mixture was directly loaded onto a flash column (DCM to DCM/EA = 20: 1) to give (lS,5S,6S)-methyl 3- ((teri-butoxycarbonyl)((2-(trimethylsilyl)ethoxy)methyl)amino)-5-(5-((Z)-2-(5- chloropyrazin-2-yl)-2-fluorovinyl)-2-fluorophenyl)-5 -methyl -2 -thia-4-azabicyclo [4.1.0]hept- 3-ene-l-carboxylate (22 mg, 35percent yield) as a gum. To neat ( 3-((teri-butoxycarbonyl)((2- (trimethylsilyl)ethoxy)methyl)amino)-5-(5-((Z)-2-(5-chloropyrazin-2-yl)-2-fluorovinyl)-2- fluorophenyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-l-carboxylate (22 mg, 0.032 mmol) was added 0.2 mL of 96percent sulfuric acid. After stirring for 10 minutes (mix thoroughly), the reaction was quenched with sat. NaHCC>3 to pH = 8 and was extracted with DCM three times. The combined organic phases was dried over sodium sulfate, and concentrated. Flash chromatography (S1O2, DCM/EtOAc = 10: 1 to 4: 1 to 2: 1) gave (15′,55′,6S)-methyl 3-amino-5-(5-((Z)-2-(5-chloropyrazin-2-yl)-2-fluorovinyl)-2- fluorophenyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-l-carboxylate (Example 149) (13 mg, 0.029 mmol, 89 percent yield) as a white solid. MS m/z = 451 (M+H). l NMR (300 MHz, CDCI3) delta 8.65 (s, 1H), 8.56 (s, 1H), 7.99 (d, J=7.45 Hz, 1H), 7.64-7.81 (m, 1H), 7.00- 7.20 (m, 2H), 3.81 (s, 3H), 2.58 (t, J=8.62 Hz, 1H), 1.77 (s, 3H), 1.57 (dd, J=4.82, 9.50 Hz, 1H), 1.10-1.21 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19745-07-4, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BOURBEAU, Matthew, P.; BROWN, James, A.; CHEN, Ning; FROHN, Michael, J.; LIU, Longbin; LIU, Qingyian; PETTUS, Liping, H.; QIAN, Wenyuan; REEVES, Corey, M.; SIEGMUND, Aaron, C.; (509 pag.)WO2017/24180; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem