Tag: M.W=100-200

Application 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.

0.378 g (3.330 mmol) of 3-hydrazinopyrazine in 12.5 ml of ethanol was added to 0.600 g (2.561 mmol) of methyl 4-oxo-3-(phenylcarbonyl)pentanoate, and the mixture was heated at 135 C. in a sealed vessel in a microwave oven for 1.5 h. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane and washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.115 g (13.8% of theory) of a light-yellow wax.NMR (CDCl3, 300 MHz): 2.39 (s, 3H); 3.40 (s, 2H); 3.69 (s, 3H); 7.23 (m, 2H); 7.39 (m, 3H); 8.22 (dd, 1H); 8.38 (dd, 1H); 8.66 (d, 1H).

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

Reference:
Patent; JAKOBI, Harald; Martelletti, Arianna; Tiebes, Joerg; Dittgen, Jan; Feucht, Dieter; Haeuser-Hahn, Isolde; Kehne, Heinz; Rosinger, Christopher Hugh; US2010/160164; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 98-97-5,Some common heterocyclic compound, 98-97-5, name is Pyrazine-2-carboxylic acid, molecular formula is C5H4N2O2, 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.

REFERENCE EXAMPLE 8-42-pyrazinemethanol (Compound CD)Step 1; To methanol (8.0 mL), thionyl chloride (2.08 mL) was added dropwise under a nitrogen atmosphere at -10 C. and the mixture was stirred at the same temperature for 30 minutes. To this, 2-pyrazinecarboxylic acid (1.00 g, 8.06 mmol) was added at the same temperature and the mixture was stirred at room temperature for 72 hours. The reaction mixture was concentrated, a saturated aqueous sodium bicarbonate solution was added to the residue, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol 19/1) to give methyl 2-pyrazinecarboxylate (969 mg, yield: 87%).1H-NMR (270 MHz, CDCl3, delta); 4.06 (s, 3H), 8.74 (dd, J=1.3, 2.3 Hz, 1H), 8.79 (d, J=1.3 Hz, 1H), 9.34 (d, J=2.3 Hz, 1H).

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-carboxylic acid, its application will become more common.

Reference:
Patent; Amishiro, Nobuyoshi; Fukuda, Yuichi; Kinpara, Keisuke; Mie, Motoya; Tagaya, Hisashi; Takahashi, Takeshi; US2011/237584; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 22047-25-2,Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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.

General procedure: A solution of the selected aldehyde or ketone (10 mmol) in10 cm3 absolute ethanol was gradually added to a warm stirred solution of 1.68 g hydrazide 1 (10 mmol) in 40 cm3 absolute ethanol and 2 cm3 glacial acetic acid. The reaction mixture was then heated under reflux while stirring for 1 h. The formed beige precipitates were filtered, washed with cold 50% ethanol, air dried, and crystallized from the appropriate solvent.

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

Reference:
Article; Chaaban, Ibrahim; El Khawass, El Sayeda M.; Abd El Razik, Heba A.; El Salamouni, Nehad S.; Ghareeb, Doaa A.; Abdel Wahab, Abeer E.; Monatshefte fur Chemie; vol. 149; 1; (2018); p. 127 – 139;,
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 77112-52-8 as follows. Recommanded Product: Ethyl imidazo[1,2-a]pyrazine-2-carboxylate

0.46 M HCl-EtOH (169 mL) and 10% Pd-C (50% wet) (1.37 g) were added to the EtOH (546 mL) solution of imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester (13.7 g). The mixture was hydrogenated under H2 at 40 psi at room temperature for 15 h. The reaction mixture was filtered and Pd-C was washed with EtOH. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with CHCl3-MeOH (9/1~2/1). The titled compound was obtained as brown crystals Yield: 10.4 g, 63%. 1H NMR(CDCl3)delta d 1.38(t, 3H, J=7.1 Hz), 3.90(t, 2H, J=5.7 Hz), 4.40(q, 2H, J=7.1 Hz), 4.59(t, 2H, J=5.7 Hz), 4.80(s, 2H), 8.20(s, 1H).

According to the analysis of related databases, 77112-52-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2006/276445; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 19838-08-5, name is 3-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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. Recommanded Product: 3-Methylpyrazin-2-amine

A.2: Chemical Synthesis for compounds N-alkylatbetad deriva- tives (R31 ? H)Starting material: (3-Chloro-phenyl) – ( 8-methyl-2-phenyl- imidazo [1, 2-a]pyrazin-3-yl) -amineTo a stirred solution of 3-methyl-2-pyrazineamine (10.9 g, 100 mmol; see Example 1.1), benzaldehyde (15.9 g, 150 mmol) and Yb(OTf)3 (3.1 g, 5 mol%, 5 mmol) in abs. MeOH (200 mL) 3-chlorophenylisonitrile (15.1 g, 110 mmol) as a solution in abs. MeOH (100 mL) was added under argon. The reaction mixture was allowed to stir overnight (18 h) and after TLC control for additional 5 hours more until the starting 3-methyl-2-pyrazineamine was comsumed. The reaction mixture was concentrated to 1/3 of its initial vol- ume and was cooled down to -100C for crystallization. After approx. 2 days in a freezer light-yellow precipitate deposited. It was collected by filtration, washed with several portions of pre-cooled abs. MeOH (-100C) and dried under high vacuum for 24 h. MS: m/z = 335.7 (M++l; MW = 334.81); HPLC: Rt = 2.00 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19838-08-5, its application will become more common.

Reference:
Patent; ONCALIS AG; CAPRARO, Hans-Georg; WO2010/83617; (2010); 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. 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of Imidazo[1,2-a]pyrazine-2-carboxylic acid

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

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; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486460-21-3, 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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

HATU (490 mg, 1.3 mmol) followed by DIPEA (450 pi, 2.6 mmol) was added to astirred solution of 3 -(6-chloro-3-cyanoquinolin-4-yl)-3-azabicyclo [4.1. Ojheptane-6-carboxylic acid (280 mg, 0.86 mmol) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro- [1,2,4jtriazolo[4,3-ajpyrazine hydrochloride (240 mg, 1.0 mmol) in DMF (4.3 mL) at room temperature. The resulting mixture was stirred at room temperature for 15 hours, then diluted with water and extracted with EtOAc (3x). The combined organic layers were washed withwater (2x) and brine, then dried with Na2SO4, filtered and concentrated. The residue was purified by MPLC (24 g Si02 0->100% [(3:1) EtOH:EtOAcj:hexanes) to provide racemic product. MS: 502 (M + 1).The racemic product was further resolved by SFC (Column Whelk O(S,S) (2 x 25 cm) 45% (2:1) iPOH:MeCN (0.1% NH4OH)/C02) to provide 6-chloro-4- ((1 S,6R)-6-(3-(trifluoromethyl)-5 ,6,7, 8-tetrahydro- [1 ,2,4jtriazolo[4,3 -aj pyrazine-7-carbonyl)-3-azabicyclo[4.1.Ojheptan-3-yl)quinoline-3-carbonitrile (peak 1, SFC tR = 4.38 mm) (HumanCYP8B1 1C50 (nM) 1288). MS: 502 (M + 1) and 6-chloro-4-((1R,68)-6-(3-(trifluoromethyl)-5,6,7, 8-tetrahydro- [1 ,2,4jtriazolo [4,3-al pyrazine-7-carbonyl)-3 -azabicyclo [4.1. Ojheptan-3 -yl)quinoline-3-carbonitrile (peak 2, SFC tR = 5.29 mm) (Human CYP8B1 1C50 (nM) 1926).MS: 502 (M

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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route of 186534-02-1, A common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

10052] In 10 mL of methanol was dissolved 2,4-dimeth- ylphenylhydrazide hydrochloride (1.72 g, 10 mmol). To the solution, 3,5,6-trimethylpyrazine-2-carbaldehyde (1.50 g, 12 mmol) was added with an ice-bath under the protection of N2. After the mixture was stirred for 10 mm, a lot of brick red precipitate showed and the reaction was then complete. The mixture was filtered through a suction funnel, and the brick red solid was transferred to a vacuum oven to be dried for using directly in the next reaction step of the reaction. The red brick intermediate (3.04 g, 10 mmol) was dissolved in 25 mL of methanol, and 1.68 ml of anhydrous triethylamine and 1.7 ml of trifluoroacetic anhydride were added respectively with an ice-bath under the protection of N2, and the reaction was run for 30 minutes. The reaction was monitored by TLC till completion. The resulting material was extracted with Ethyl acetate, dried over anhydrous Na2504, separated by a silica gel colunm (ethyl acetate:petroleum ether=1 :3) to get T-006 as a light yellow solid (3.25 g, 89.3%). ESI-MS: [M+H] mlz 365.1. ?H-NMR (CDC13, 300 MHz) oe: 2.1 (s, 3H), 2.42 (s, 3H), 2.46 (s, 3H), 2.54 (s, 3H), 2.85 (s, 3H), 7.08 (d, j=7.05 Hz, 1H), 7.24 (d, J=7.21 Hz, 1H), 7.25 (s, 1H), 7.55 (s, 1H); Anal.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU MAGPIE PHARMACEUTICALS CO., LTD.; WANG, Yuqiang; CHEN, Haiyun; ZHANG, Zaijun; ZHANG, Gaoxiao; YU, Pei; SUN, Yewei; SHAN, Luchen; TAO, Liang; US2018/346430; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, 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 122-05-4, SDS of cas: 122-05-4

9.35 g (167 mmol) of potassium hydroxide and 11 g (65 mmol) of 2,5-pyrazinedicarboxylic acid (3) were dissolved in water (200 ml). To this solution, 5% Pd / C catalyst was added at a rate of 5 mol% with respect to the reaction substrate, hydrogen (1 MPa) was supplied while heating to 50 C.And the hydrogenation reaction was carried out for 18 hours. It was confirmed with a gas chromatograph that raw materials were consumed and the reaction proceeded quantitatively. An aqueous solution of the product was obtained by filtering the reaction solution to remove the catalyst. This product has a measurement result obtained by 1 H NMR measurement in the reference (Witichemistry described in J. Med. Chem. 1985, 28, 1228-1234), ak, DT; Nair, RV; Schmid, FA, “Synthesis and antimetastatic properties of stereoisomeric tricyclic bis (dioxopiperazines) in the Lewis lung carcinoma model” By agreement with the shift value, it was confirmed that it was 2,5-piperazine dicarboxylic acid (4).

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; IHI Corporation; Waseda University; Sato, Yutaka; Kanomata, Norihiro; Yuchi, Takeshi; (19 pag.)JP2018/140981; (2018); A;,
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. 274-82-8, name is [1,2,4]Triazolo[4,3-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 274-82-8

To a solution of [1,2,4]triazolo[4,3-a]pyrazine (1.50 g) in MeOH (150 mL) was added PtO2 (1.10 g) and 10% Pd/C (0.46 g) at rt. The suspension was stirred under H2 at room temperature for 16 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column to give the title compound (0.18 g, 11.54%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 125.1 (M+1).

The synthetic route of 274-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem