Tag: M.W=100-200

Application of 6164-79-0,Some common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, 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.

The 4- (3-CHLORO-4- (2-PYAZINYLMETHOXY) anilino) -5-fluoroquinazoline used as starting material was obtained as follows: Methylpyrazine carboxylate (8.5g) was stirred in water (200 ml) and sodium borohydride (11.65 g) was added in one portion, resulting in a vigorous exotherm. The reaction mixture was stirred vigorously for 30 minutes, and then ethanol (80 ML) and saturated potassium carbonate (150 ml) were added. The mixture was stirred for 30 minutes and then extracted with ethyl acetate (5 x 150 ml) and DCM (5 x 150 ml). The combined extracts were dried and concentrated to give pyrazin-2-ylmethanol as a yellow oil (5.43 g, 80%), which was used without purification; NMR spectrum (DMSO-D6) 4.65 (s, 2H), 5.57 (br s, 1H), 8.54 (d, 2H), 8.71 (s, 1H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/93880; (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. 274-45-3, name is Pyrrolo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Pyrrolo[1,2-a]pyrazine

PREPARATION EXAMPLE 13 Preparation of 6-and 8-chloropyrrolo-[1,2-a]pyrazine 3.6 g of pyrrolo[1,2-a]pyrazine prepared in Preparation Example 1 was dissolved in a mixture of 20 ml of dimethyl sulfoxide and 20 ml of ethyl acetate; and 4.8 g of N-chloro succinimide was added thereto. The reaction mixture was stirred at 60 C. for 6 hours, poured into ice-water, extracted with ethyl acetate(100 ml*3), and then concentrated under a reduced pressure. The residue was chromatographed over silica gel to obtain 0.6 g of 6-chloropyrrolo[1,2-a]pyrazine and 0.4 g of 8-chloropyrrolo[1,2-a]pyrazine, respectively.

The synthetic route of 274-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yuhan Corporation; US5593984; (1997); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 136927-64-5, name is 1-Chloropyrrolo[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 136927-64-5, Computed Properties of C7H5ClN2

Compound C4 (63.0 mg, 0.294 mmol), 1-chloropyrrolo[1,2-a]pyrazine (32.5 mg,0.21 mmol), and cesium carbonate (208 mg, 0.64 mmol) were combined in dimethylsulfoxide (1.0 mL), and the mixture was degassed with nitrogen for 5 minutes. After the reaction mixture had been heated to 120 C for 72 hours, it was cooled to room temperature, diluted with ethyl acetate, and filtered through diatomaceous earth. The filter pad was rinsed with ethyl acetate, and the combined filtrates were washed with 1:1water I saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered,and concentrated in vacuo. Purification using silica gel chromatography (Gradient: 0%to 5% methanol in dichloromethane) afforded the product as a white solid. Yield: 34 mg,0.10 mmol, 48%. LCMS m/z 331.1 [M+H]. 1H NMR (400 MHz, CDCI3) oe 9.00 (5, 1H),7.62 (d, J=4.8 Hz, 1H), 7.47-7.45 (m, 1H), 7.28-7.22 (m, 2H), 7.11-7.09 (m, 2H), 6.99-6.98 (m, 1H), 6.86-6.85 (m, 1H), 2.29 (5, 6H), 2.05 (5, 3H).

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; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); 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. 22047-25-2, name is Acetylpyrazine, A new synthetic method of this compound is introduced below., name: Acetylpyrazine

General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid.

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Klemens, Tomasz; ?witlicka, Anna; Machura, Barbara; Kula, S?awomir; Krompiec, Stanis?aw; ?aba, Katarzyna; Korzec, Mateusz; Siwy, Mariola; Janeczek, Henryk; Schab-Balcerzak, Ewa; Szalkowski, Marcin; Grzelak, Justyna; Ma?kowski, Sebastian; Dyes and Pigments; vol. 163; (2019); p. 86 – 101;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 14508-49-7, 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. 14508-49-7 name is 2-Chloropyrazine, 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.

Step 1 To a solution of chloropyrazine (11.5 g, 0.1 mmol) in absolute ethanol (50 ml) was added anhydrous hydrazine (16 ml, 0.5 mmol) and the reaction mixture was refluxed for 3 h. The organics were removed in vacuo and the residue was extracted with benzene to give hydrazinopyrazine (4.2 g).

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

Reference:
Patent; Syntex (U.S.A.) LLC; US6316464; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 54013-07-9, 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 54013-07-9 as follows.

Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (26 mg, 0.084 mmol, prepared as described in Synthesis 62 and 63), 5-methoxypyrazin-2-amine (16 mg, 0.127 mmol), cesium carbonate (55 mg, 0.169 mmol), 4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene (3.9 mg, 7 mol%), and tris(dibenzylideneacetone)dipalladium chloroform complex (3.5 mg, 3.5 mol%) were added to a vial which was flushed with nitrogen and sealed. Anhydrous toluene (0.3 mL) and DMF (0.1 mL) were added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated by microwave irradiation at 1300C for 30 minutes. The cooled solution was diluted with methanol and adsorbed onto an lsolute SCX-II column. The column was washed with methanol, then with 2M ammonia in methanol. The basic fractions concentrated. Preparative TLC, eluting with ethyl acetate – methanol – concentrated ammonia 10:1:0.2, gave methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3- ylamino)nicotinate (5 mg, 15%) as an oil.1H NMR (500 MHz, MeOH) delta 8.56 (1 H, s), 8.43 (1 H, s), 7.93 (1 H, s), 7.00 (1 H, s), 3.95 (3H, s), 3.84 (3H, s), 3.62-3.70 (2H, m), 2.60 (3H, s), 2.20-2.38 (4H, m), 2.00-2.10 (3H, m), 1.73-1.84 (2H, m). LCMS (3) Rt 1.70 min; m/z (ESI+) 399 (MH+).

According to the analysis of related databases, 54013-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

HATU (15.91 g, 41.8 mmol) was added to a stirred, cooled 0 C mixture of (6R,8aS)-3-oxooctahydroindolizine-6-carboxylic acid (7.3 g, 39.8 mmol), (3- chloropyrazin-2-yl)methanamine hydrochloride (7.89 g, 43.8 mmol) and DIPEA (10.44 ml, 59.8 mmol) in CH2C12 (25 ml) and the mixture was stirred at room temperature for 1 h. and then concentrated. The residue was purified by column chromatography on silica gel (Isco 240 g silica gel), eluting with CH2Cl2/MeOH (50/1) to give (6R,8aS)-N- ((3-chloropyrazin-2-yl)methyl)-3-oxooctahydroindolizine -6-carboxamide (11.15g, 36.1 mmol, 91 % yield) as a white solid. LC-MS: Ret. time 1.09 min; m/z 309.11 (M+H)+; 1HNMR (CDCI3, 500 Hz): 8.38 (1H, d, J = 2 Hz), 8.25 (1H, d, J = 2 Hz), 7.37 (1H, dd, J = 4 and 4.5 Hz), 4.56-4.72 (2H, m,l), 4.29 (1H, dd, J = 13 and 4.5 Hz),3.42-3.47 (m,l), 2.81 (1H, t, J = 13 Hz), 2.35 (2H, t, J = 8 Hz), 2.17-2.23 (1H, m), 2.04 (1H, d, J = 13.5 Hz), 1.94-1.96 (1H, m), 1.74-1.82 (1H, m), 1.55-1.62 (1H, m), 1.16-1.24 (1H, m).

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 SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

Oxalyl chloride (1.7 mL, 19 mmol) was added to a suspension of 5-chloropyrazine-2- carboxylic acid (CAS no. 36070-80-1) (2.53 g, 16.0 mmol) in dichloromethane (25 mL) and DMF (4 drops) at RT and under argon. The mixture was allowed to stir for 1.5h, concentrated in vacuo to and the residue was re-dissolved in dichloromethane (25 mL). Dimethylamine (2M in THF, 8.77 mL, 17.6 mmol) was then added dropwise followed by triethylamine (4.9 mL, 35 mmol) and allowed to stir for a further 5.5 hours. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in dichloromethane and filtered. The filtrate was chromatographed on silica, eluting with a gradient of 50- 100% ethyl acetate in isohexanes to give the desired compound (1.88 g).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/50117; (2008); 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. 6905-47-1, name is 2-Amino-6-methoxypyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. name: 2-Amino-6-methoxypyrazine

The 3-amino-2-chloro-5-methoxypyrazine used as a starting material were prepared asfollows :-N-Chlorosuccinimide (1.7 g) was added portionwise to a solution of 2-amino-6-methoxypyrazine (S K Vohra et al, J. Org. Chem., 1979,44,1128; 1.6 g) in chloroform(26 ml) and the resultant mixture was stirred at ambient temperature for 3 hours. Silica gel(10 g) was added and the solvents were evaporated. The residue was purified by columnchromatography on silica gel using methylene chloride as eluent. There were thus obtained inturn :- 2-amino-3,5-dichloro-6-methoxypyrazine (0.253 g); NMR Spectrum: (CDC13) 3.95(s, 3H), 4.83 (m, 2H); Mass Spectrum: M+ET1″ 194; a sample of 3-amino-2-chloro-5-methoxypyrazine that was contaminated with succinimide and 5-amino-2-chloro-3-methoxypyrazine (0.339 g); NMR Spectrum: (CDC13) 3.95 (s, 3H), 4.27 (m, 2H), 7.32(s, 1H); Mass Spectrum: M+H* 160. The fraction containing 3-amino-2-chloro-5-methoxypyrazine was purified further by column chromatography on silica gel eluting with a10:1 mixture of petroleum ether (b.p. 40-60C) and ethyl acetate. There was thus obtainedpurified material (0.94 g); NMR Spectrum: (CDC13) 3.87 (s, 3H), 4.82 (m, 2H), 7.36 (s, 1H);Mass Spectrum: M+H+ 160.

The synthetic route of 6905-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/108711; (2004); 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. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H3ClN2

General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

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; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; vol. 423; 1; (2014); p. 11 – 15;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem