Tag: M.W=200-300

Application of 1458-16-8, The chemical industry reduces the impact on the environment during synthesis 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

To a methanol (10 ml) and tetrahydrofuran (10 ml) solution of 3-amino-6-iodopyrazine-2-carboxylic acid methyl ester (see Patent Document:)(2.0 g, 7.16 mmol), a 1 M aqueous sodium hydroxide solution (14.3 ml) was added under ice cooling and the mixture was stirred for 2 hours under ice cooling. The reaction solution was charged with a 1 M aqueous hydrochloric acid solution to render the reaction system acidic and concentrated to obtain crude 3-amino-6-iodopyrazine-2-carboxylic acid.

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, Methyl 3-amino-6-iodopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

Pd(dppf)CI2 (158 mg, 0.215 mmol) was added to a suspension of methyl 3-amino-6- bromopyrazine-2-carboxylate (1.00 g, 4.31 mmol), ethylboronic acid (0.637 g, 8.62 mmol) and K2CO3 (1.79 g, 12.9 mmol) in DME (20 ml). The resultant suspension was de-gassed by bubbling a stream of nitrogen through the reaction mixture for 1 min. The reaction mixture was heated at 90 C for 17 h then allowed to cool to RT. The reaction was recharged with ethylboronic acid (318 mg, 4.31 mmol) and Pd(dppf)Cl2 (79 mg, 0.11 mmol) then heated at 90 C for 2 h. The reaction mixture was allowed to cool to RT then added to saturated aq. NaHC03 solution (40 ml). The resultant mixture was extracted with EtOAc (2×40 ml) then the combined organic extracts were washed with brine (40 ml), dried over MgS0 , filtered and concentrated in vacuo. The crude material was purified by flash column chromatography on a silica column (50 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 6:94 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a yellow solid (322 mg, 41 %).1H NMR (250 MHz, CDCl3 ) delta 8.14 (s, 1 H), 6.27 (s, 2H), 3.98 (s, 3H), 2.79 (q, J = 7.6 Hz, 2H), 1.29 (t, J = 7.6 Hz, 3H).LC/MS (System A): m/z (ESI+) = 182 [MH+], Rt = 0.81 min, UV purity = 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 762240-92-6, 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. 762240-92-6 name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, 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.

Example-17:Preparation of (R)-3-azido-l-(3-(trifluoromethyl)-5,6-dihydro-[l,2,4] triazolo[43-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-l-one.;To 6 gms of (R)-methyl 3-azido-4-(2,4,5-trifluorophenyl)butanoate, added 30 ml of water and 30 ml of tetrahydrofuran. Added 2.0 gms of lithium hydroxide and stirred the reaction mixture for 4 hrs at 25-300C temperature. Acidify the reaction mixture using cone, hydrochloric acid and extracted the compound using ethyl acetate. Distilled off the solvent completely under reduced pressure. To the obtained residue added 24 ml of dimethylformamide and cooled the reaction mixture to 0-50C. 3.5 gms of N,N’- dicyclohexylcarbodiimide (DCC) was dissolved in 10 ml of dimethylformamide and make upto 20 ml. Added 7 ml of above prepared NjN’-dicyclohexylcarbodiimide (DCC) solution to the above 0-50C cooled reaction mixture. Added 3.5 gms of 3- (trifluoromethyl)-5,6,7,8-tetra hydro-[l,2,4]triazolo[4,3-a]pyrazine hydrochloride and 3.3 ml of triethylamine to the reaction mixture and stirred for 15 minutes. Added 0.75 gms of dimethylaminopyridine (DMAP) and stirred the reaction mixture for 3 hrs at 0-50C. Added 6.5 ml of N,N’-dicyclohexylcarbodiimide solution and stirred for 3 hrs. Again added 6.5 ml of N,N’-dicyclohexylcarbodiimide solution and stirred for 3 hrs at 0-50C. Raised the temperature to 25C and stirred the reaction mixture for 12 hrs at same temperature. The unwanted precipitated solids were separated by filtration and to the filtrate added water and ethyl acetate. Separated the both aqueous and organic layers. Washed the organic layer with 5% hydrochloric acid solution followed by washed with 5% sodium bicarbonate solution. Distilled off the solvent completely under reduced pressure. Added 30 ml of isopropyl alcohol to the obtained compound and stirred for 45 minutes at 25-300C temperature. Filtered the precipitated solid and dried the material. To the obtained compound added 10 ml of isopropyl alcohol and 3.8 ml of cone, hydrochloric acid. Stirred the reaction mixture for 3 hrs at 500C. Cooled the reaction mixture to 25C and added water. Extracted the compound from reaction mixture with methylene chloride. Distilled off the solvent completely to get the title compound. Yield: 4.5 gms.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; SATYANARAYANA, Revu; KONDAL REDDY, Bairy; SRINIVAS, Aluru; WO2010/122578; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Amino-6-bromopyrazine-2-carboxylic acid

(v) 3-Amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide To a solution of the product of step (iv) (100 g, 0.45 mol) in DMF (350 mL) was added TEA (129 mL, 0.91 mol) and 3-aminopyridine (42.3 g, 0.45 mol). HATU (174 g, 0.45 mol) was added to the solution portionwise. The suspension was filtered, washed with water and dried under a reduced pressure to afford the subtitle compound (v) as a yellow solid (105g). 1H-NMR (400 MHz, CDC13) delta 9.50 (s, 1H), 8.81 (d, 1H), 8.40 (dd, 1H), 8.32 (s, 1H), 8.23- 8.20 (m, 1H), 7.33 (dd, 1H). LCMS (ESI) m/z [M+H]+=294&296 (calc=294&296) (MultiMode+), HPLC Retention Time = 0.478 min.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FENG, Tao; SANGANEE, Hitesh, Jayantilal; WADA, Hiroki; WO2011/89416; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0, 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. 32111-21-0, name is 2-Iodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step B: A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[l,3,2]-dioxa-borolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzene sulfonamide (2, 0.650 g, 1.08 mmol).in.N,N-dimethylformamide (10 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.33 g, 1.616 mmol), cesium carbonate (0.701 g, 2.15 mmol), Pd(dppf)2Cl2 (0.087 g, 0.107 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100 0C for 2.5 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SC>4, concentrated, and purified by preparative HPLC to afford 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5- dihydro-pyrazolo[3,4-d]pyrimidin-l-yl]-benzene sulfonamide (3). 1H NMR (DMSO-d6, 400 MHz) delta 9.25 (s, IH), 8.71 (m, IH), 8.63 (d, IH), 8.58 (m, 2H), 8.45 (m, IH), 8.07 (m, 2H)5 7.80 (m, 2H), 7.59 (m, 4H), 7.45 (m, 4H); LC-MS calculated for C27H18C1N7O3S (M+H*) 556.1, found 555.9.

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

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0, 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. 32111-21-0, name is 2-Iodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

4.4 ml of tetrabutylammonium fluoride (1M solution in THF) are added to a solution of 450 mg (2.18 mmol) of iodopyrazine, 647 mg (3.28 mmol) of 5-chloro-3-methoxy-2-(prop-2-ynyloxy)-pyridine (Example P7), 83 mg (0.44 mmol) of copper(l) iodide and 153 mg (0.22 mmol) of bis(triphenylphosphine)palladium dichloride (Pd(PPh3)2CI2) in 14 ml of dioxane. The reaction mixture is stirred for 3 hours at 50C under an argon atmosphere and is then allowed to cool to 20C. The solvent is removed under reduced pressure and the crude product obtained is purified by means of flash chromatography (eluant: ethyl acetate/petroleum ether 1/2). The desired title compound is obtained as a brown solid having a melting point of 142C in a yield of 510 mg (84 % of theory). Rf = 0.50 in ethyl acetate/petroleum ether 1/1;1H NMR (CDCI3): delta(ppm)= 3.89 (s, 3H); 5.29 (s, 2H); 7.08 (d, J=2.2 Hz, 1H); 7.71 (d, J=2.2 Hz, 1H); 8.48 (d, J=2.5 Hz, 1H); 8.52 (dxd, J=1.3 and 2.5 Hz, 1H); 8.66 (d, J=1.3 Hz, 1H).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2003/104206; (2003); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 117103-53-4,Some common heterocyclic compound, 117103-53-4, name is 2-Bromo-5-nitropyrazine, molecular formula is C4H2BrN3O2, 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.

Step 1. Preparation of Dimethyl-[2-(5-nitro-pyrazin-2-yloxy)-ethyl]-amine To a 100 ml dried round bottom flask was added bromonitropyrazine (300 mg, 1.47 mmol, Eq: 1.00) and CH3CN (10 ml). To the mixture was added K2CO3 (203 mg, 1.47 mmol, Eq: 1.00) under argon to afford a light yellow slurry. To the slurry was added N,N-dimethylaminothanol (131 mg, 148 mul, 1.47 mmol, Eq: 1.00) dropwise. The reaction became an orange slurry and was stirred at room temperature overnight. The reaction mixture was filtered and the filter cake was washed with CH3CN (3*20 mL). The combined filtrate and washes were concentrated in vacuo and purified by column chromatography eluting with 5-10% (10% NH4OH in MeOH) in 1/1 EtOAc/Hex eluent to afford 270 mg (87%) of the title compound.

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

Reference:
Patent; Berthel, Steven Joseph; Billedeau, Roland Joseph; Brotherton-Pleiss, Christine E.; Firooznia, Fariborz; Gabriel, Stephen Deems; Han, Xiaochun; Hilgenkamp, Ramona; Jaime-Figueroa, Saul; Kocer, Buelent; Lopez-Tapia, Francisco Javier; Lou, Yan; Orzechowski, Lucja; Owens, Timothy D.; Tan, Jenny; Wovkulich, Peter Michael; US2012/40949; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 143591-61-1, A common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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.

If one were to add 0.8 eq of benzylmagnesium bromide, in ether at -78C with 5% Palladium tetrakistriphenylphosphine under Nitrogen, to compound 161a then one would obtain compound 161b after workup using techniques known in the art.

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; SCHERING CORPORATION; WO2009/73777; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87486-34-8, These common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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.

5-Bromo-3-(4-(1,4-dimethyl-3-oxopiperazin-2-yl)phenylamino)-1-methylpyrazin-2(1H)-one (14); A 100-mL three-neck round-bottomed flask equipped with a mechanical stirrer and reflux condenser was charged with (4) (780 mg, 3.56 mmol), 13 (998 mg, 3.73 mmol), cesium carbonate (2.36 g, 7.26 mmol) and 1,4-dioxane (40 mL). After bubbling nitrogen through the resulting solution for 30 minutes, Xantphos (0.162 g, 0.281 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.15 g, 0.165 mmol) were added, and the reaction mixture was heated at reflux for 16 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting residue was absorbed onto silica gel and purified by flash chromatography to afford a 57percent yield (818 mg) of 14 as an orange solid: mp 206-207¡ã C.; 1H NMR (500 MHz, CDCl3) delta 8.27 (bs, 1H), 7.72 (dd, 1H, J=2.0, 8.5 Hz), 7.36 (dd, 2H, J=2.0, 8.5 Hz), 6.73 (s, 1H), 3.71 (m, 1H), 3.69 (s, 1H), 3.52 (s, 3H), 3.21 (m, 1H), 3.01 (m, 1H), 2.97 (s, 3H), 2.67 (m, 1H), 2.19 (s, 3H); MS (ESI+) m/z 406 (M+H).

Statistics shows that 3,5-Dibromo-1-methylpyrazin-2(1H)-one is playing an increasingly important role. we look forward to future research findings about 87486-34-8.

Reference:
Patent; Zhao, Zhongdong; Zhichkin, Pavel E.; Stafford, Douglas G.; Kropf, Jeffrey E.; BLOMGREN, Peter A.; Currie, Kevin S.; Lee, Seung H.; Mitchell, Scott A.; Xu, Jianjun; Schmitt, Aaron C.; US2009/82330; (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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 6966-01-4

0.15 eq. palladium (II) acetate and 0.2 eq. 1,1′-bis(diphenylphosphino)-ferrocene were combined in dimethylformamide under nitrogen and heated to 50 C. for 20 minutes. R3 and n are each as defined herein. The reaction was allowed to cool to room temperature and 1.0 eq. of the pyrazine, 1.5 eq. of the boronic acid and 1.15 eq. of triethylamine were added. The reaction was heated to 90 for 12 hours and allowed to cool to room temperature. The DMF was removed by rotary evaporation. The crude reaction mixture was dissolved in chloroform and washed twice with 1N aq. HCl and then twice with saturated aq. NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered and concentrated. Material was purified by silica gel chromatography using 100% chloroform as eluent.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2004/180905; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem