Tag: M.W=100-200

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. 6164-79-0, name is Methyl 2-pyrazinecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-pyrazinecarboxylate

Example 261; 5-Phenyl-2-(3-pyrazin-2-yl-ureido)-thiophene-3-carboxylic acid (S)-azepan-3-ylamide pyrazine-2-carbohydrazide. ; To a stirred solution of methyl pyrazine-2-carboxylate (11.1 g, 80 mmol) in 140 mL of EtOH was added hydrazine hydrate (15.6 mL, 320 mmol). The resultant solution was heated to reflux for 2h. The solvent was removed under reduced pressure and dried under high vacuum to yield the title amide (11.1 g, 100%) as a white solid. The product was used in subsequent steps without purification.’H NMR (d6-DMSO 8 10.1, br s, 1H; 8 9.12, d, 1H ; 8 8. 83, d, 1H ; 8 8.70, dd, 1H; 8 4.64, br s, 2H), LC/MS (APCI, ES, M+H=139).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/66163; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. Recommanded Product: 2-Amino-5-bromopyrazine

Step 4: A solution of 2-amino-5-bromopyrazine (600 mg, 3.45 mmol), tetrakis(triphenyl-phospine)palladium(0) (186 mg, 0.17 mmol) and NaSCH3 (490 mg, 7 mmol) in DMF (20 mL) was warmed at 60 C. overnight in a sealed tube. The reaction mixture was poured onto water and aqueous NaHCO3 and extracted 3 times into CH2Cl2/ether. The combined organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (silica, 0-20% ethyl acetate/hexanes gradient) afforded 5-methylsulfanyl-pyrazin-2-ylamine (305 mg, 63%): 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 2.52 (s, 3H) 4.48 (br. s., 2H) 7.91 (d, J=1.51 Hz, 1H) 7.98 (d, J=1.51 Hz, 1H).

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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 16298-03-6, Recommanded Product: Methyl 2-aminopyrazine-3-carboxylate

Example 58; Step 1; A solution of bromine (10 mL, 190 mmol) in acetic acid (10 mL) was added dropwise to a solution of 1 (20 g, 130 mmol) in glacial acetic acid (100 mL) at 45¡ã C. The resulting mixture was stirred at 25¡ã C. for 30 min. After completion of reaction (reaction progress was monitored by TLC), the solution was diluted with water (600 mL) and then stirred at RT for another 30 min. A yellow solid precipitated out, which was filtered, washed with water and dried to afford compound 2 as yellow solid (28.5 g, 93percent). MS m/z (ES): 232 (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, Methyl 2-aminopyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 l-methyl-4,5,6,7-tetrahydro-lH-indazole-4-carboxylic acid (6 g, 33 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (6 g, 33 mmol) in 200 mL of DCM was added TEA (9 g, 88 mmol) dropwise. The resulting mixture was stirred at room temperature for 5 mins, and then HATU (12.5 g, 33 mmol) was added to the solution in portions at 0 C. The mixture was stirred at room temperature for 2 hours. Water was added, the DCM layers was separated, and washed with brine, dried over Na2S04. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF = 5/1 v/v%) to afford N-((3-chloropyrazin-2- yl)methyl)-l-methyl-4,5,6,7-tetrahydro-lH-indazole-4-carboxamide (1.5 g, 15 %). MS-ESI (m/z): 306 (M+l) + (Acq Method: 10-80AB_2min_220&254.1cm; Rt: 0.93 min)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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 55557-52-3, category: Pyrazines

A mixture of the respective boronic acid derivative (B-B(OH)2) (21.5 mmol), 3-chloro- pyrazine-2-carbonitrile (21.5 mmol), a solution of K2CO3 (59.4 mmol) in water (30 ml_),PPh3 (3. 2 mmol), Pd(OAc)2 (1.05 mmol) in dry DME was stirred at reflux under inert atmosphere for 16 h. After cooling to rt, the reaction mixture was diluted with EtOAc, filtered over celite, the filtrate was dried over MgSO4, filtered and concentrated in vacuo to yield the desired pyrazine-2-carbonitrile derivative which was used for the next step without further purification3-m-Tolyl -pyrazine-2-carbonitrile prepared by reaction with commercially available 3-m-tolyl-boronic acid LC-MS: tR = 0.88 min; [M+H+MeCN]+ = 243.63

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, 3-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; HAZEMANN, Julien; KOBERSTEIN, Ralf; SIEGRIST, Romain; SIFFERLEN, Thierry; WO2010/4507; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 768-05-8, A common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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.

Potassium hydroxide 11.5 g (0.20 mol) was dissolved in absolute ethanol (400 mL) at ambient temperature. Then pyrazine-2-carbohydrazide (2) 40g (0.299 mole) added and reaction mass was cooled. Carbon disulfide 25.08 g (0.33 mol) added in small portions and the mixture was stirred at reflux temperature for 12 h. The reaction mixture changed to green colour with the evolution of hydrogen sulfide. The completion of reaction was monitored by TLC (Chloroform 9.5: Methanol 0.5). Ethanol completely distilled under vacuum below 50C. The reaction mass cooled to 25-30C. Water (100 mL) added to dissolve salts and pH 6.0-7.0 adjusted by conc. HCl (20 mL). Solid precipitated out. Stir at 25-30C for 1h, solid filtered, water (50 mL) washing given and dried to give white to off white solid compound (3) 36.32 g (70.00%). Thus yield obtained was used in the next step without further purification. mp- 208-210C. IR (KBr, cm-1): 3352.4 (-NH2 stretch), 3230.3 (>NH stretch), 2845 (-OCH3), 1640.65 (>C=O stretch), 764 (>C-Br); 1H NMR (400 MHz, DMSO-d6 ppm): delta 8.76 (s, 1H), 8.80 (s, 1H), 9.19 (s, 1H), 14.82 (s, 1H). 13C NMR (400MHz, DMSO-d6 ppm): 138.58 (pyrazine C-N), 143.45 (pyrazine C=N), 145.28 (pyrazine C=N), 147.29 (pyrazine C=N), 158.32 (-C=O), 178.48 (-C-SH). MS: 178.9; m/z: 179.9 (M+H).

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; Patil, Sanjeev R.; Asrondkar, Ashish; Patil, Vrushali; Sangshetti, Jaiprakash N.; Kalam Khan, Firoz A.; Damale, Manoj G.; Patil, Rajendra H.; Bobade, Anil S.; Shinde, Devanand B.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3845 – 3850;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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. HPLC of Formula: C8H10N2O

General procedure: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography. 3.2.1. 2,6-Bis-(3,5,6-trimethyl-pyrazin-2-ylmethylene)-cyclohexanone (5a)Yield: 74%; Mp: 112e113 C; 1H NMR (500 MHz, CDCl3) d: 7.87 (s,2H), 2.55 (s, 6H); 2.51 (s, 6H); 2.48 (s, 6H); 2.37 (t, J 8.0 Hz, 4H),1.85 (m, 2H); 13C NMR (500 MHz, CDCl3) d: 181.2,152.7,150.4,149.6,147.9, 146.2, 141.4, 27.9, 27.1, 17.1, 16.8, 16.1; HRMS (ESI) m/z:363.4754 [MH], Microanalysis calculated for C22H26N4O(362.47), C: 72.90%, H: 7.23%, N: 15.46%. Found C: 72.96%, H: 7.25%,N: 15.42%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 186534-02-1, its application will become more common.

Reference:
Article; Zha, Gao-Feng; Qin, Hua-Li; Youssif, Bahaa G.M.; Amjad, Muhammad Wahab; Raja, Maria Abdul Ghafoor; Abdelazeem, Ahmed H.; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 34 – 48;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 95-89-6, The chemical industry reduces the impact on the environment during synthesis 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, I believe this compound will play a more active role in future production and life.

[1-ETHYLPROPYLAMINE] (1.0 mmol) followed by sodium tert-butoxide (1.25 mmol) is added to a mixture of 2-chloro-3,6-dimethylpyrazine (0.83 mmol), tris (dibenzylideneacetone) dipalladium [(0)] (2 mol%), and BINAP (6 mol%) in ethyleneglycol dimethyl ether (2 mL) under nitrogen. The mixture is stirred at 70-80C for 2.5 hours, diluted with aqueous ammonium chloride, and extracted 1: 1 hexane-Et20. Combined extracts are dried (sodium sulfate), filtered, concentrated, and chromatographed on silica gel (10: 1 to 4: 1 hexane-EtOAc eluent) to give the aminopyrazine.

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, 3-Chloro-2,5-dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/18437; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

Sulfuric acid (19 mu, 0.36 mmol) was added to a methanol (1.2 mL, 29 mmol) solution of pyrazine-2,5-dicarboxylic acid (Ark Pharma cat AK-76746, 100 mg, 0.6 mmol). Then the mixture was allowed to stir at 90 C overnight. After cooling to rt, the mixture was diluted with methanol and basified with NaOH aq. Then the mixture was allowed to stir at rt for 5 h to reach -50% conversion to afford the mono-ester. Then the mixture was acidified with HC1 aq, and extracted with DCM/iPrOH x 3. The organic layer was dried and concentrated to afford desired product, which was used in the next step without further purification. LC-MS calculated for C7H7N2O4 (M+H)+: m/z = 183.0; found 183.0.

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

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; YU, Zhiyong; ZHANG, Fenglei; YAO, Wenqing; (173 pag.)WO2017/106634; (2017); 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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7F3N4

A mixture of (3S,4S)-i -(6-chloro-3-cyanoquinolin-4-yl)-3 -methoxypiperidine-4-carboxylic acid (65 mg, 0.187 mmol), 3-(trifluoromethyl)-5,6,7,8-tetrahydro- [1,2,4jtriazolo[4,3-ajpyrazine (40 mg, 0.206 mmol), HATU (142 mg, 0.375 mmol) and DIPEA (131 1iL, 0.749 mmol) in DMF (3 mL) was stirred at 16 C for 1.5 h. Water (20 mL)was added and the mixture was extracted with EtOAc (3 x 8 mL). The combined organic layers were dried with Na2504, filtered and concentrated. The residue was purified by prepHPLC then dried by lyophilization to 6-chloro-4- [(3S,48)-3 -methoxy-4- { [3 -(trifluoromethyl)5 ,6-dihydro [1 ,2,4jtriazolo [4,3-al pyrazin-7(8H)-ylj carbonyl } piperidin- 1 -ylj quinoline-3- carbonitrile (Human CYP8B 1 150 (nM) 22) and 6-chloro-4- [(3S,4R)-3-methoxy-4- { [3-(trifluoromethyl)-5 ,6-dihydro [1 ,2,4jtriazolo[4,3 -ajpyrazin-7(8B)-ylj carbonyl } piperidin- 1- yljquinoline-3-carbonitrile (Human CYP8B1 1C50 (nM) 441). MS: 556 (M + 1).

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 486460-21-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LI, Derun; LIU, Hong; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; (170 pag.)WO2018/34918; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem