Tag: M.W=100-200

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. 274-79-3, name is Imidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Imidazo[1,2-a]pyrazine

Imidazo[1 ,2-a]pyrazine(l1 ) (4.38 g, 36.8 mmol) was dissolved in methanol (100 mL) and hydrogenated at 1 atm/25 0C hydrogen over platinum(IV) oxide (0.522 g, 1.838 mmol) for 24 h. The catalyst was filtered and the filtrate concentrated to afford afford product in 4.8 g that was used without further purification. LC/MS = 124 (M+H)+, retention time = 0.34 minutes (2 minute method (high pH)).

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 274-79-3.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[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 69214-33-1, Safety of 8-Chloroimidazo[1,2-a]pyrazine

Intermediate Example 2-1 : Preparation of 3-bromo-8-chloro-imidazo[1 ,2- ajpyrazineTo a stirred solution of 8-chloro-imidazo[1 ,2-a]pyrazine (164.2 g g, 1070 mmol) in 950 mL DMF is added NBS (190.3 g, 1070 mmol) in one portion and the mixture is stirred overnight at rt. The mixture is poured on 9500 mL water, filterd and the residue is washed with water (2 x 1000 mL) and dried in vaccuo to yield 152.6 g (61.4 %) of the title compound. 1H-NMR (300 MHz, d6-DMSO): delta =8.45 (d, 1 H), 8.00 (s, 1 H), 7.83 (d, 1 H) ppm.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 123-32-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 123-32-0 as follows.

Example 5 BSc4352: 4,4′-(1E,1’E)-2,2′-(pyrazine-2,5-diyl)bis(ethene-2,1-diyl)bis(N,N-dimethylaniline) Synthesis: 2,5-Dimethylpyrazine (0.125 g, 1.16 mmol) is dissolved in 10 ml dimethylformamide, followed by addition of 4-(dimethylamino)benzaldehyde (0.345 g, 2.32 mmol) and potassium-t-butoxide (0.26 g, 2.32 mmol). The solution is heated for 4 h to 80 C. and allowed to cool to room temperature. In this process, a solid crystallizes out. The solution containing the crystallized solid is filtered and washed with ethyl acetate. After drying under high-vacuum, 0.308 g (yield: 72%) of the product BSc4352 is obtained as red solid.1H-NMR (CDCl3, 500 MHz): delta=8.49 (s, 2H), 7.62 (d, J=16 Hz, 2H), 7.49 (d, J=8.9 Hz, 4H), 6.96 (d, J=16 Hz, 2H), 6.72 (d, J=8.9 Hz, 4H), 3.02 (s, 12H) ppm13C-NMR (CDCl3, 125 MHz): delta=149.7, 148.0, 141.7, 132.8, 127.5, 123.7, 118.7, 111.2, 39.3 ppm.

According to the analysis of related databases, 123-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KLINIKUM DARMSTADT GMBH; TECHNISCHE UNIVERSITAT DARMSTADT; LUDWIG-MAXIMILIANS-UNIVERSITAT MUNCHEN; Schmidt, Boris; Kieser, Daniel; Bolaender, Alexander; Herms, Jochen; Haussen, Roland Heyny-Von; Gu, Jiamin; US2013/287700; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-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.

2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65% (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93% (13.6 g; 94.07 mmol); HPLC-MS: (M+H)+=145/147; tRet=0.34 min; method FECB5.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; GIANNI, Davide; SMETHURST, Christian; US2014/142098; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6705-33-5, 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. 6705-33-5 name is Pyrazin-2-ylmethanol, 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.

To a stirred solution pyrazin-2-ylmethanol (500 mg, 4.545 mmol) in DCM (20 ml) was added Dess-martin periodinane (2.89 g, 6.818 mmol) and stirred for 1 hr at RT. Reaction mass was diluted with DCM (100 ml) washed with saturated sodium bicarbonate solution (50 ml X 2) twice. DCM part was separated, dried over sodium sulfate, evaporated to dryness to get 300 mg crude, which was purified by column chromatography using 100-200 silica and 20% EtOAc in hexane as eluent to afford pyrazine-2-carbaldehyde (100 mg) as brown liquid.

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

Reference:
Patent; CURADEV PHARMA PVT. LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Veejendra K; KAPOOR, Kishore Kamal; WO2014/141110; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, HPLC of Formula: C5H7Cl2N3

N,N-diisopropylethylamine (109 mmol, 18.01 ml) and a solution of benzyl 3-(chlorocarbonyl)azetidine-1- carboxylate (5.53 g) in dichloromethane (32.5 ml) were added to a stirred suspension of 2-aminomethyl-3- chloropyrazine hydrochloride (content 77%; 21.80 mmol, 5.10 g) in dichloromethane (55 ml) at room temperature to give a dark brown solution. After stirring at room temperature for two hours the reaction mixture was quenched with water and filtered over decalite. Layers were separated and to the aqueous layer saturated aqueous sodium hydrogencarbonate solution was added and the layer was extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane / methanol gradient 10/0 to 9/1 ) to give benzyl 3-((3-chloropyrazin-2- yl)methylcarbamoyl)azetidine-1-carboxylate (6.46 g).NMR (CDCl3, 400 MHz): delta 3.37 -3.45 (m, 1 H), 4.16 – 4.30 (m, 4H), 4.71 (d, J = 5 Hz, 2H), 5.10 (s, 2H), 6.92 – 6.97 (m, 1 H), 7.28 – 7.47 (m, 5H), 8.33 (d, J = 2 Hz, 1 H), 8.44 (d, J = 2 Hz, 1 H).

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; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 54608-52-5, A common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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.

441 mg (2.0 mmol) of the compound from Example 12A and 220 mg (2.0 mmol) of the compound from Example 3A are initially charged in 10 ml of ethanol. 93 mg (0.4 mmol) of camphor-10-sulfonic acid are added, and the mixture is stirred under reflux for 5 h. The mixture is allowed to cool to RT, and the solid formed is filtered off and washed once with a little ethanol. 10 ml of a 4 N solution of hydrogen chloride in dioxane are then added, and the mixture is stirred at RT for 30 min. The mixture is then concentrated on a rotary evaporator, and the residue is dried under high vacuum.Yield: 260 mg (47% of theory)LC-MS (Method 1): Rt=1.93 min; MS (ESIpos): m/z=240 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=9.70 (s, 1H), 9.43 (s, 1H), 9.08 (d, 1H), 9.01 (s, 1H), 8.70 (d, 1H), 8.61 (s, 2H), 8.08 (dd, 1H).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, A new synthetic method of this compound is introduced below., Formula: C5H7N3

Intermediate 2: 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide 1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (2.4 mL, 18 mmol) was added to a solution of 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-phenylmethoxy-benzoic acid (Intermediate 3) (6.19 g, 15 mmol) in DCM (100 mL) and stirred at ambient temperature for 30 minutes. Further 1-chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.24 mL, 1.8 mmol) was added and stirring continued for 20 minutes. 5-Methylpyrazin-2-amine (CAS no. 5521-58-4) (3.34 g, 31 mmol) and pyridine (2.5 mL, 31 mmol) were added and the reaction stirred for a further 16 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (350 mL), washed with water (2*100 mL) and brine (100 mL), dried (MgSO4), and evaporated under reduced pressure. The residue was purified by flash chromatography, eluding with a gradient of 50-75% ethyl acetate in isohexane, to afford the product (4.01 g, 53%). 1H NMR delta (400 MHz, CDCl3) 2.28 (quintet, 2H), 2.49 (s, 3H), 4.18 (t, 2H), 4.63 (t, 2H), 5.05 (s, 2H), 6.78 (s, 1H), 7.10 (s, 1H), 7.25-7.37 (m, 7H), 8.04 (d, 1H), 8.07 (s, 1H), 8.25 (s, 2H), 9.46 (s, 1H); m/z 496 (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:
Patent; AstraZeneca AB; US2008/171734; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 108-50-9 as follows. Computed Properties of C6H8N2

1-Bromo-2,5-pyrrolidinedione (0.055 mol) and then dibenzoyl peroxide (cat.quant.) were added to a mixture of 2,6-dimethylpyrazine (0.05 mol) in CCl4 (100ml). The mixture was stirred and refluxed for 4 hours, stirred at room temperature under N2 flow overnight, cooled on an ice bath and filtered. The filtrate was evaporated, to give residue 1. NaH (0.04 mol) was added to a solution of intermediate (1) (0.04 mol) in DMF (150ml). The mixture was stirred at room temperature under N2 flow for 1 hour. Residue 1 was dissolved in DMF (50ml) and added dropwise to the mixture. The mixture was stirred at 50C overnight. DMF was evaporated. The residue was taken up in H2O and the mixture was extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated. Yield: 6.82g of intermediate (2) (32%).

According to the analysis of related databases, 108-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; EP1418175; (2004); 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. 681249-57-0, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (780 mg, 2.65 mmol) was dissolved in 15 mL of N, N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N, N, N’, N’-tetramethyluronium hexafluorophosphate (1.80 g, 4.77 mmol), 2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine 19a (560 mg, 2.92 mmol, prepared according to a known method disclosed by ‘patent application ‘) and N, N-diisopropylethylamine (1.4 mL, 7.95 mmol). After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure, added with 30 mL of H2O, extracted with ethyl acetate (30 mL*3). The organic phase was combined, washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[4-fluoro-3-[2-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-phthalazin-1-one 19 (205 mg, yield 16.4%) as a light yellow solid. MS m/z (ESI): 473.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.67 (br. s, 1H), 8.48 (s, 1H), 7.77 (m, 3H), 7.42 (m, 2H), 7.11 (t, 1H), 5.10 (s, 1H), 4.75 (s ,1H),4.39 (s, 2H), 4.32 (d, 3H), 3.88 (s, 1H)

The synthetic route of 681249-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Co., Ltd.; TANG, Pengcho; LI, Xin; LI, Xiangqin; CHEN, Yang; WANG, Bin; ZHU, Zhe; EP2604610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem