Tag: M.W=100-200

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. 41110-28-5, name is 3-Methylpyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3-Methylpyrazine-2-carboxylic acid

To a stirred solution of MeOH (50 mL) was added SOCl2(8.6 g, 72.4 mmol) dropwise at 0C. Then 3-methylpyrazine-2-carboxylic acid (5 g, 36.2 mmol) was added to the reaction. The mixture was stirred at 60 C overnight. The mixture was concentrated under reduced pressure and the residue was dissolved into EA (50mL) . The organic phase was washed with saturated aq.NaHCO3(50 mL) . The organic phase was washed with brine, dried over Na2SO4and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluted with: EA/PE = 1/1) to afford the title compound as yellow solid (3.9g, yield: 70.9%) . MS: M/e 153 (M+1)+.

The synthetic route of 41110-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); 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. 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4F2N2O2

Example 211 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-5-chloro-4-fluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide The title compound was synthesized by procedures and steps analogous to those described in Method A2, Example 206 above, but using 5-(difluoromethyl)pyrazine-2-carboxylic acid (Aurigene Discovery Technologies Ltd.) in step 10. MS m/z=482.1 [M+H]+. Calculated for C18H14ClF6N5O2: 481.779 1H NMR (400 MHz, CHLOROFORM-d) delta=9.61 (br. s., 1H), 9.51 (s, 1H), 8.91 (s, 1H), 8.18 (dd, J=2.5, 6.1 Hz, 1H), 7.44-7.35 (m, 1H), 7.02-6.60 (m, 1H), 4.35 (br. s., 2H), 4.11-3.96 (m, 1H), 2.80 (dd, J=2.2, 13.9 Hz, 1H), 1.92 (t, J=13.2 Hz, 1H), 1.65 (s, 3H)

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; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, 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. category: Pyrazines

PZEH was synthesized by the condensation reaction of2-acetylpyrazine with hydrazine hydrate, with the loss of awater molecule. Hydrazine hydrate (0.1 ml, 2.05 mmol) wasadded to an ethanolic solution (10 ml) of 2-acetylpyrazine(0.251 g, 2.05 mmol). The solution was heated under reflux forabout 4 h with constant stirring and was then left to cool toroom temperature overnight to give a cream-coloured solid.The crude product was filtered off, dried in the air andrecrystallized from an EtOH/MeCN mixture to affordcolourless crystals that were suitable for X-ray diffraction. It isworth mentioning that PZEH will undergo further condensationto form the azine on standing at room temperature(yield 0.105 g, 37%; m.p. 394-395 K). Analysis calculated forC6H8N4 (%): C 52.93, H 5.92, N 41.15; found (%): C 52.95, H4.96, N 39.61; IR (cm1, KBr pellet): 3394 (s, N-H), 3318 (m,N-H), 3182 (s, aryl C-H), 2913 (m, alkyl C-H), 1657 (s,C N), 1592 (s, aryl C C), 1511 (s), 1100 (s); 1H NMR(CDCl3): 9.19 (1H, s, Ar-H), 8.43-8.42 (1H, m, Ar-H), 8.38(1H, d, Ar-H), 5.73 (2H, s, -N-NH2), 2.20 (3H, s, -C-CH3);13C NMR (CDCl3): 151.73 (C N), [144.85, 142.57, 142.48,142.36] (py-C), 8.89 (-CH3); MS/EI (m/z) (I, %) for C6H8N4: 136 [M]+ (100), 107 [C6H7N2]+ (59), 79 [C4H3N2]+ (83), 57[C2H5N2]+ (89), 52 [C2N2]+ (68).

The synthetic route of Acetylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kassim, Muhammad Arif; Yassin, Ubaidullah H. M.; Tan, Ai Ling; Usman, Anwar; Hamid, Malai Haniti S. A.; Acta Crystallographica Section C: Structural Chemistry; vol. 74; 4; (2018); p. 424 – 427;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

14508-49-7, name is 2-Chloropyrazine, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-Chloropyrazine

20.0 g (174.6 mmol) 2-chloropyrazine are added dropwise to 60.0 ml (61.7 g, 1.2 mol) hydrazine hydrate. The mixture is stirred at a bath temperature of 120 C. for 45 min. For working up, the cooled reaction mixture is left to stand at 2 C. for 12 h, the crystals which have precipitated out are filtered off and the residue on the filter is washed twice with petroleum ether. The residue is then recrystallized from toluene.Yield: 6.5 g (34% of th.)LC-MS (Method 1): Rt=0.49 min; MS (ESIpos): m/z=111 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=8.11 (s, 1H), 7.94 (s, 1H), 7.90 (s, 1H), 7.70 (d, 1H), 4.29 (br. s, 2H).

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14399-37-2,Some common heterocyclic compound, 14399-37-2, name is 3,6-Dichloropyrazin-2-amine, molecular formula is C4H3Cl2N3, 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 three-necked round-bottle flask was added Y7d (200 mg, 1.22 mmol, 1 equiv), dioxane (4 mL). The solution was vacuated and purged with nitrogen gas three times. Xantphos (l4mg, 0.024 mmol, 0.02 equiv), PdCh(dppf) (8.9 mg, 0.012 mmol, 0.1 equiv), and DIPEA (0.32 g, 2.44 mmol, 2.0 equiv) were added under nitrogen atmosphere. The solution was heated to 85 C for overnight. The reaction was cooled and evaporated. The residue was purified by columnchromatography (eluent/ethyl acetate/heptane = 1/1) to give Zl7d (259 mg, 0.99 mmol, 81%). ‘H NMR (400 MHz, CDCb) d = 7.83 (s, 1H), 4.88 (bs, 2H), 3.73 (s, 3H), 3.47 (t, J= 9.2 Hz, 2H), 2.79 (t, J= 9.2 Hz, 2H).

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

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; LU, Gang; WAN, Yinbo; WANG, Jianhua; WU, Quanbing; ZHANG, Hao; (116 pag.)WO2020/65453; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Methyl 5-chloropyrazine-2-carboxylate (100 mg, 0.579 mmol, 1 eq), 1-methylpiperazine (65 mul, 0579 mmol, 1 eq) and potassium carbonate (161 mg, 1.159 mmol, 2 eq) were heated in DMSO in a microwave reactor at 120 C. for 5 min. The reaction mixture was poured onto an SCX column (10 g), washed with methanol then eluted with 2M ammonia in methanol. The reaction was repeated as above with methyl 5-chloropyrazine-2-carboxylate (150 mg), 1-methylpiperazine (98 mul) and potassium carbonate (241 mg) in DMSO (3 ml). The product fractions from both reactions were combined and evaporated under vacuum to afford the product as a yellow solid (283 mg, 83%). 1H NMR (399.902 MHz, DMSO) delta 2.23 (s, 3H), 2.42 (t, 4H), 3.73 (t, 4H), 3.82 (s, 3H), 8.38 (d, 1H), 8.66 (d, 1H). MS: m/z 237 (MH+).

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

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
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. 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3F3N4

A mixture of 250 mg (1.33 mmol) of 3-(trifluoromethyl)[l,2,4]triazolo[4,3-a]pyrazine(Intermediate 6, Step A), 0.479 mL (4.66 mmol) of 30% hydrogen peroxide aqueous solution, and 2 mLof glacial acetic acid was stirred at 95 C. After 8 h, the solution was cooled and concentrated. Theresidue was partitioned between dichloromethane and saturated sodium bicarbonate aqueous solution.Thin-layer chromatography on silica gel (90:10:1 dichloromethane:methanol:concentrated ammoniumhydroxide solution) revealed that the product was in the aqueous phase. Therefore, the aqueous solutionwas concentrated to dryness, and the residue was purified by preparative HPLC (C18 reverse phasecolumn, 0-50% acetonitrile in water containing 0.05% trifluoroacetic acid) to provide the title compoundas a white solid. LC-MS 205 (M+l).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 486460-20-2.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313339-92-3, 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. 313339-92-3 name is 3,5-Dichloropyrazine-2-carbonitrile, 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.

2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]benzenesulfonamide (5.78 g) and 3,5-dichloro – pyrazine-2-carbonitrile (2.35g), 1,1′- bis (diphenylphosphino) ferrocene – dichloropalladium (II) (Pd (dppf) 2Cl2) (791mg) and cesium carbonate (13.2g) was added to a reaction vessel equipped with a magnetic stir bar, then add 100ml of dioxane and 10ml water, stirring the mixture was heated to 100 c for 3h the reaction mixture was cooled to room temperature and treated with saturated aqueous sodium bicarbonate (lml) quenched and extracted with EtOAc (3 X 200ml). the combined aqueous phases were dried over sodium sulfate, filtered and evaporated to give the crude product as a brown oil. using EtOAc and purified by silica gel chromatography using heptane as eluent fast, the solvent was evaporated the solvent under reduced pressure to give a light brown foam 2,3-dichloro-N-[4-(6-chloro-5-cyanopyrazin-2-yl)phenyl]benzenesulfonamide yield:. 4·32g (73%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Sanofi; Nazare, M; HALLAND, N; SCHMIDT, F; WEISS, T; Dietz, U; Hofmeister, A; (76 pag.)CN103012407; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 274-79-3, name is Imidazo[1,2-a]pyrazine, 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 274-79-3, Safety of Imidazo[1,2-a]pyrazine

The title compound was prepared from imidazo[1,2-a]pyrazine (500 mg, 4.20 mmol, from Step A) and platinum oxide (250 mg) in methanol (50 mL), using a procedure analogous to that described in Example 1, Step B. Concentration gave the title compound (512 mg) as a viscous oil. 1H NMR (500 MHz, CD3OD) delta 3.37 (t, 1H, J=5.5 Hz), 4.18 (t, 2H, J=5.6 Hz), 4.88 (s, 1H), 7.27 (d, J=1.6 Hz, 1H), 7.33 (d, 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, Imidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4774-14-5,Some common heterocyclic compound, 4774-14-5, name is 2,6-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.

2,2,6,6-tetramethylpiperidine (2.84 g, 20.1 mmol) in THF (250 mL) at -100C was added n-butyllithium (13.8 mL, 22.1 mmol). The solution was stirred for 20 minutes and cooled to -90C. 2,6-Dichloropyrazine (3.0 g, 20.1 mmol) in THF (10 mL) was added to the solution followed by carbon dioxide (89 g, 2014 mmol) as dry ice powder. The mixture was then allowed to warm to room temperature while stirring. The reaction mixture was concentrated under reduced pressure, diluted with water (20OmL) and acidified with 10% aq. HCl solution to pH 2. Extraction with EtOAc (x3) was followed by extraction with saturated aq. NaHCO3 solution. The aquous solution was acidified carefully with 10% aq. HCl solution to pH 2. The solution was extracted with EtOAc(x3) and the resulting solution was washed with water and brine. The organics were dried over anhydrous MgSO4 and concentrated. The resulting solid was trituated with Hex/chloroform (1 :1) and the remaining solid was filtered and washed with hexane to provide the title compound as an off-white solid (1.78 g, 9.22 mmol, 45.8% yield); IH NMR (400 MHz, DMSO-J6) delta ppm 8.90 (s, 1 H).

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

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem