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., 6164-79-0

Step 2; Lithium aluminum hydride (40.0 mg, 1.06 mmol) was suspended in tetrahydrofuran (1.0 mL). To this, a solution of methyl 2-pyrazinecarboxylate (66.0 mg, 0.478 mmol) in tetrahydrofuran (0.5 mL) was added dropwise under a nitrogen atmosphere at 0 C. and the mixture was stirred at the same temperature for 15 minutes. Then, water (40 muL), a 15% aqueous sodium hydroxide solution (40 muL) and water (120 muL) were successively added to the reaction mixture and the mixture was stirred at room temperature for 1 hour. The mixture was filtered through Celite and the mother liquid was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 2-pyrazinemethanol (Compound CD) (19.0 yield: 36%).1H-NMR (270 MHz, CDCl3, delta): 3.11 (brd, J=5.6 Hz, 1H), 4.85 (d, J=5.6 Hz, 1H), 8.52-8.55 (m, 2H), 8.64 (s, 1H).

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; Amishiro, Nobuyoshi; Fukuda, Yuichi; Kinpara, Keisuke; Mie, Motoya; Tagaya, Hisashi; Takahashi, Takeshi; US2011/237584; (2011); 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. 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below., 486460-20-2

3- (TRIFLUOROMETHYL)-1, 2, 4-triazolo [4,3-a] pyrazine (540 mg, 2.87 mmol, from Step A) was hydrogenated under atmospheric hydrogen with 10% Pd/C (200 mg) as a catalyst in ethanol (10 mL) at ambient temperature for 18 h. Filtration through Celite followed by concentration gave a dark colored oil. Dichloromethane was added to the above oil and the insoluble black precipitate was filtered off. Concentration of the filtrate gave the title compound as an OIL. H NMR (500 MHz, CDC13) 8 2.21 (br, 1H), 3.29 (t, 2H, J = 5.5 Hz), 4.09 (t, 2H, J = 5.5 Hz), 4.24 (s, 2H). MS (M+1) 193.

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; MERCK & CO., INC.; WO2004/58266; (2004); 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. 20737-42-2, name is 3-Oxo-3,4-dihydropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 20737-42-2

Preparation of (S)-3-(4-cyanophenyl)-2-((4-(((5-fluoro-1H-benzo[d]imidazol- 2-yl)methyl)amino)-6-((3-((4-(3-hydroxypyrazine-2-carbonyl)piperazin-1- yl)methyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)-N,N-dimethylpropanamide (TA1021). HATU (1.2 equiv., 34 mg, 0.093 mmol) was added to a solution of 3-hydroxypyrazine-2- carboxylic acid (I-6, 1.1equiv., 12 mg, 0.080 mmol, Synthonix, Fisher Scientific) in anhydrous DCM (0.70 mL) and DIPEA (3equiv., 0.040 mL, 0.23 mmol). After being stirred at r.t. for 10 minutes, TA1013 (50 mg, 0.080 mmol) was added. The reaction was stirred at r.t. until the LCMS analysis showed complete consumption of the starting material (3-24h). The crude residue was then purified by reverse phase preparative HPLC (XBridge BEH, 19×150 mm, 5mum, C18 column; ACN/water with 0.1% formic acid modifier, 20mL/min), affording Compound TA1021 (17.3 mg, 29%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) d 12.20 (s, 1H), 8.95 (d, J = 24.1 Hz, 1H), 8.07- 7.87 (m, 1H), 7.84- 7.68 (m, 1H), 7.68- 7.41 (m, 4H), 7.40- 7.22 (m, 2H), 7.22- 6.78 (m, 3H), 6.56 (s, 1H), 5.18- 4.91 (m, 1H), 4.79- 4.50 (m, 2H), 3.74- 3.39 (m, 7H), 3.28- 3.13 (m, 4H), 3.12- 2.78 (m, 5H), 2.75- 2.66 (m, 1H), 2.61 (s, 1H), 2.48- 2.02 (m, 4H). MS (m/z): 771 [M+1]+, LCMS purity: 99%.

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; ADURO BIOTECH, INC.; KATIBAH, George Edwin; KIM, Jung Yun; NDUBAKU, Chudi Obioma; ROBERTS, Tucker Curran; TJANDRA, Meiliana; (165 pag.)WO2019/245910; (2019); 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., 486460-21-3

VI (2.0g, 5.0mmol) and 3- (trifluoromethyl) -5,6,7,8-tetrahydro – [1,2,4] triazolo [4,3-a] pyrazine (of 0.912 g , 4.7mmol) Was dissolved in 20ml of anhydrous N, N- dimethylformamide was added HOBt (0.770g, 5.7mmol) and EDC ¡¤ HCL (1.092g, 5.7mmol), stirred at room temperature 20h. After the reaction was added 20ml of water and 20ml of ethyl acetate, there Phase was washed with water 3 times, washed three times with saturated aqueous sodium carbonate solution, the organic phase was dried over anhydrous sodium sulfate, suction filtered, and concentrated to give yellow Colored foamy solid 2.967g, crude yield> 100%, recrystallized from ethyl acetate, filtration and drying to give a yellow solid 1.827g, Recrystallization yield of 63.6%.

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; Shanghai Institute Of Pharmaceutical Industry; China State Institute of Pharmaceutical Industry; Meng, Xiangguo; Cai, Zhengyan; Zhou, Weicheng; Jiang, Jingzhang; Zhu, Yijun; Ge, Yuanyuan; Yan, Pingping; (32 pag.)CN103172635; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, 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. 4858-85-9 name is 2,3-Dichloropyrazine, 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.

Reference Production Example 19 A mixture of 3.73 g of 2,3-dichloropyrazine, 8.80 g of diethyl malonate, 30 ml of dimethyl sulfoxide and 17.9 g of cesium carbonate was stirred for 8 hours at 110C under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, then, to this was added ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 3.67 g of the resultant residue was subjected to silica gel column chromatography, to obtain 2.69 g of diethyl (3-chloro-2-pyrazinyl) malonate. 1H-NMR (CDCl3, TMS) delta (ppm): 1.27 (6 H, t, J=7.2 Hz), 4.30 (4 H, q, J=7.2 Hz), 5.20 (1 H, s), 8.36 (1 H, d, J=2.6 Hz), 8.50 (1 H, d, J=2.6 Hz)

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

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1958946; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19745-07-4, A common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Into a 250 ml 3-necked round bottom flask, was placed 45percent hydriodic acid (60 ml). To this was added sodium iodide (25 g, 0.17 mol). To the mixture was added XV-B-86 (10.5 g, 0.07 mol). The resulting solution was allowed to react at room temperature. Adjustment of the pH to >8 was accomplished by the addition of 20 g NaOH in 50 g ice to afford XV-C-86.

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5780-66-5, name is Pyrazine-2-carbaldehyde, molecular formula is C5H4N2O, 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. 5780-66-5

EXAMPLE 2; This example describes synthesis of another mid-transition metal complex of the invention, with ligand synthesis as illustrated in Scheme 3 and described in part (a), and metallation as illustrated in Scheme 4 and described in part (b). [00163] (a) The imine-containing ligand 3 may be synthesized by reaction of 2,6-pyrazine carboxaldehyde with 2,6-diisopropylanine as illustrated in Scheme 3: [C00023] [00164] A 250-mL flask is charged with 2,6-pyrazine carboxaldehyde and methanol. A slight excess of 2,6-diisopropylaniline (1.1 eq) is added by pipet. The mixture is stirred at room temperature in methanol for 1 d. The solvent and unreacted aniline are removed in vacuo to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5780-66-5, its application will become more common.

Reference:
Patent; SRI International; US6841676; (2005); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19745-07-4, Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4.

Step A: ethyl \ 1 -(5 -chloropyrazm-2-y )piperidm-4-yl] acetate2,5-Dichloropyrazine (1.42 g, 9.53 mmol, 1.0 equiv.) and ethyl piperidin-4-ylacetate(1.66 g, 9.69 mmol, 1.02 equiv.) were dissolved in DMF (23 mL) and stirred at roomtemperature. Cesium carbonate (5.0 g, 15.35 mmol, 1.61 equiv.) was added and the resulting reaction suspension was stirred in a 55¡ãC oil bath for 3 hrs while under N2(g)- The reaction suspension was filtered to remove solids and to collect the DMF solution, which was mostly concentrated to a suspension. The suspension was dissolved in EtOAc / 13/40. After shaking, theEtOAc phase was dried over Na2S04, filtered, and concentrated to a residue. Purification with Biotage SP-1 [ SNAP lOOg cartridge Hexanes:EtOAc 0 > 10percent 2CV; 10 > 80percent 10CV; 80percent 2CV ] isolated the desired product. LC-MS (ES, m z): Ci3Hl8ClN302: 283; Found: 284[M+Hf.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; BALKOVEC, James, M.; KRIKORIAN, Arto, D.; GUIADEEN, Deodial; YANG, Ginger; JIAN, Tianying; WU, Zhicai; YU, Yang; NARGUND, Ravi, P.; VACHAL, Petr; DEVITA, Robert, J.; HE, Shuwen; LAI, Zhong; BLEVIS-BAL, Radhika, M.; CERNAK, Timothy, A.; SPERBECK, Donald, M.; HONG, Qingmei; WO2012/96813; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, 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. 5521-58-4

(i) A solution of bromine (0.11 ml) in chloroform (20 ml) was added dropwise over 20 minutes to a solution of 2-amino-5-methylpyrazine (0.218 g) in chloroform (30 ml) which was protected from light. The reaction mixture was stirred for 90 minutes after addition was complete and was then washed with water (50 ml). The organic phase was dried (MgSO4) and volatile material was removed by evaporation to give a yellow oil. The oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-3-bromo-5-methylpyrazine (0.286 g) as white solid, m.p. 51-52 C.; mass spectrum (positive chemical ionisation (+ve CI)): 188 (M+H)+.

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 5521-58-4.

Reference:
Patent; Zeneca Ltd.; US5668137; (1997); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19745-07-4, 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. 19745-07-4, name is 2,5-Dichloropyrazine, A new synthetic method of this compound is introduced below.

A mixture of tert-butyl (R)-3-(3-amino-4-((trans-4-((tert- butyldimethylsilyl)oxy)cyclohexyl)(isobutyl)amino)phenyl)butanoate (500 mg, 0.97 mmol), 2,5-dichloropyrazine (290 mg, 1 .94mmol), Pd2(dba)3 (178 mg, 0.194 mmol), Xantphos (225 mg, 0.388 mmol) and CS2CO3 (630 mg, 1 .94 mmol) in toluene (5 ml.) was stirred at 100C under N2 atmosphere overnight. The resulting mixture was partitioned between EtOAc and H20. After the layers were separated, the organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-30% EtOAc in PE) to afford the title compound (410 mg, 67% yield). LCMS (ESI) m/z calcd for C34H55CIN4O3S1: 630.37. Found: 631 .39/633.40 (M/M+2)+.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; KAZMIERSKI, Wieslaw M.; (62 pag.)WO2019/116171; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem