Tag: M.W=300-400

Electric Literature of 58138-79-7,Some common heterocyclic compound, 58138-79-7, name is 2,6-Diiodopyrazine, molecular formula is C4H2I2N2, 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.

An oven-dried sealed tube was charged with 2-bromo-4-methyl-thiazole- 5-carboxylic acid 4-fluoro-benzylamide (1.0 g, 3.03 mmol, 1.0 equiv). The sealed tube was purged with nitrogen and Rieke zinc (10 mL, 10 g of zinc in 100 mL of tetrahydrofuran) was added. The reaction was heated in the microwave oven for 15 min 50352at 100 0C. Stirring was stopped and the remaining zinc was allowed to settle. The supernatant containing the zinc reagent was transferred via syringe to a solution of 2,6- diiodopyrazine (704 mg, 2.1 mmol, 0.7 equiv), Pd(PPh3)4 (175 mg, 0.2 mmol, 5 mol%) in tetrahydrofuran (2 mL) and dimethyl formamide (0.1 mL). The reaction mixture was purged with nitrogen for 10 min, then stirred at 140 0C for 20 hr. After cooling, the solvent was removed in vacuo and the crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 40:60, v/v] to afford 2-(6-iodo- pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fiuoro-benzylamide (100 mg, 7%). MS (M+H)+ = 455.1 , R1 = 1.53 min.

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; XENON PHARMACEUTICALS INC; WO2008/24390; (2008); A2;,
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. 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 1245644-42-1

General procedure: [0194] 6-bromo-3-iodo-imidazo[1,2-a]pyrazine 17* (0.648 g, 2 mmol) was added to a degassed mixture of dioxane(10 ml) and water (1.5 ml). The aromatic boronic acid (R2B(OH)2) (2.2 mmol) was added followed by palladium acetate(0.022 g, 5 mol%), triphenyl phosphine (0.025 g, 5 mol%) and sodium carbonate (0.32 g, 3 mmol). The reaction mixturewas stirred at 80 C under nitrogen for 18 hours. The solvent was evaporated in vacuo and the residue was partitionedbetween water (20 ml) and dichloromethane (50 ml). The dichloromethane was separated, dried over magnesium sulphateand evaporated in vacuo. The residue was purified by flash chromatography.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); 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. 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 87597-21-5

Step B: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2-yl)methanolTo a stirred solution of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate (13.95 g, 40mmol) in toluene (558 mL) at 0 C was added 80 mL DIBAH (120 mmol, 3 eq, 1 .5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2 %) (6,8-dibromoimidazo[1 ,2- a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta =8.93 (s, 1 H), 8.05 (s, 1 H), 5.46 (bs, 1 H), 4.63 (s, 2H) ppm. UPLC-MS: RT = 0.73 min; m/z 308.0 [MH+]; required MW = 307.0.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80236; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1209646-17-2,Some common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, molecular formula is C14H20N4O4, 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 suspension of I-77 (1.0 g, 3.53 mmol) in THF (20 ml) is added 1,1?-carbonyldiimidazole (0.63 g, 3.88 mmol) at room temperature. The mixture is stirred at 50 C. for 30 minutes. After this time I-19 (1.2 g, 3.88 mmol) is added as a THF solution (15 ml) and the resulting mixture is heated at 80 C. for 3 hours. The mixture is cooled and treated with AcOH (8 ml) then warmed to 80 C. and stirred over night. After this time the reaction is cooled to room temperature, concentrated and diluted with water. Extracted the product into DCM (2¡Á). The combined organics are washed with brine and dried (MgSO4). Filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford I-84 (1.2 g).

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87597-21-5, 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. 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Method A6Preparation of Intermediate I-09. Intermediate I-07 (1.00 g, 2.87 mmol) was dissolved in DCM (28 mL) and N-bromosuccinimide (0.61 g, 3.44 mmol) and trifluoroacetic acid (0.25 mL) were added. The reaction mixture was stirring at rt for 16 h and then heated at 60 C. for 2 h more. The reaction mixture was cooled, and washed with water. The organic phase was dried (Na2SO4), filtered and the solvent removed in vacuum. The residue was purified by biotage with a gradient cyclohexane/EtOAc: from 100% to 50:50 The desired fractions were collected to obtained 1.15 g of a white solid as intermediate I-09 (Y: 94%).

The synthetic route of Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1245644-42-1, These common heterocyclic compound, 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-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.

To a solution of 6-bromo-3-iodoimidazo[l ,2-a]pyrazine (3 g, 9.26 mmol) in DMF (50 mL), were added 4-cyanophenylboronic acid 3 (1.632 g, 11.1 mmol), K3P04 (4.91 g, 23.15 mmol), Pd(PPh3)4 (0.534 mg, 0.46 mmol) and water (5 mL). The reaction mixture was heated at 90 C for 1 h and water was added to the mixture to induce precipitation. The precipitate was isolated by filtration and was purified by column chromatography (silica gel, eluent petroleum ether/EtOAc 1 :1) to afford of 4-(6-bromoimidazo[l,2-a]pyrazin-3-yl)benzonitrile (2.5 g, 90%) as an off-white solid. 1H NMR (400 MHz, DMSO-< delta 9.88 (s, 1H), 8.90 (s, 1H), 8.27 (s, 1H), 8.05-7.99 (m, 4H); MS (ESI) m/z 301.1 [C13H7BrN4+2 ]+. The synthetic route of 1245644-42-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Reference of 1209646-17-2, These common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, 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 suspension of 1-77 (1.0 g, 3.53 mmol) in THF (20 ml) is added 1,1′- carbonyldiimidazole (0.63 g, 3.88 mmol) at room temperature. The mixture is stirred at 50 C for 30 minutes. After this time 1-19 (1.2 g, 3.88 mmol) is added as a THF solution (15 ml) and the resulting mixture is heated at 80C for 3 hours. The mixture is cooled and treated with AcOH (8 ml) then warmed to 80C and stirred over night. After this time the reaction is cooled to room temperature, concentrated and diluted with water.Extracted the product into DCM (2x). The combined organics are washed with brine and dried (MgS04). Filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford 1-84 (1.2 g).

Statistics shows that 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 1209646-17-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 58138-79-7, name is 2,6-Diiodopyrazine, 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 58138-79-7, Quality Control of 2,6-Diiodopyrazine

A solution of1 (0.10 g, 0.16mmol), 2,6-diiodopyrazine (25 mg, 0.08mmol)and Pd(PPh3)4 (1.5 mg, 1.3 mol) in 1.3ml of toluene wasstirred at 110 C for 10 h. The resulting residue was dissolvedin dichloromethane and washed with water three times. Theorganic layer was concentrated and the residue was purified bychromatography on silica (dichloromethane-hexane = 3:1 aseluent) to give 2,6-PD (58 mg, 72%) as a yellow solid; mp. 273275C; IR(ATR) ~ = 1595, 1493, 1449 cm1; 1HNMR (400MHz, CD2Cl2) = 0.89 (t, J = 7.4 Hz, 6H), 1.291.35(m, 4H),1.761.83(m, 4H), 4.23 (t, J = 7.2 Hz, 4H), 6.96 (dd, J =1.6 and 8.4 Hz, 2H), 7.027.06(m, 4H), 7.147.16(m, 10H),7.257.30(m,8H), 7.53 (d, J = 3.8 Hz, 2H), 7.60 (dd, J = 1.5and 8.1 Hz, 2H), 7.71 (d, J = 1.2 Hz, 2H), 7.79 (d, J = 3.8 Hz,2H), 7.95 (d, J = 8.4 Hz, 2H), 8.03 (d, J = 8.4 Hz, 2H), 8.81(s, 2H) ppm; 13CNMR (100 MHz, CD2Cl2); = 14.06, 20.86,31.46, 43.07, 105.32, 106.28, 117.54, 117.82, 118.64, 120.49,121.27, 123.01, 123.45, 124.43, 124.51, 127.57, 129.57,131.03, 137.88, 140.28, 141,65, 142.85, 147.10, 147.72,148.60, 149.68 ppm; HRMS (APCI): m/z (%): [M + H+] calcdfor C68H57N6S2, 1021.40806; found 1021.40930. (The meltingpoint of 2,6-PD is higher than that of our previous work(ref. 26) because of the improvement of the purification bychromatography.)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Diiodopyrazine, and friends who are interested can also refer to it.

Reference:
Article; Enoki, Toshiaki; Ohshita, Joji; Ooyama, Yousuke; Bulletin of the Chemical Society of Japan; vol. 91; 12; (2018); p. 1704 – 1709;,
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. 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 87597-21-5

Step B: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2-yl)methanol To a stirred solution of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate(13.95 g, 40mmol) in toluene (558 mL) at 0 C was added 80 ml_ DIBAH (120 mmol, 3 eq, 1 .5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HQ, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2 %) (6,8-dibromoimidazo[1 ,2- a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta =8.93 (s, 1 H), 8.05 (s, 1 H), 5.46 (bs, 1 H), 4.63 (s, 2H) ppm. UPLC-MS: RT = 0.73 min; m/z 308.0 [MH+]; required MW = 307.0.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem