Tag: M.W=100-200

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.

(3-chloropyrazin-2-yl)methanamine.hydrochloride (20 g, 108 mmol) and trans-4-hydroxycyclohexanecarboxylic Acid (15.54 g, 108 mmol) EDCl.HCl (22.72 g, 119 mmol), 1-hydroxy-7-azabenzotriazole (7.33 g, 53.9 mmol) in dichloromethane (250 mL) was added triethylamine (23.96 mL, 172 mmol) and the reaction mixture was stirred at room temperature over night. The mixture was washed with 0.1 M HCl-solution, 5% NaHCO3, water and brine, dried over sodium sulfate and concentrated in vacuo. The product was purified using silica gel chromatography (dichloromethane/methanol = 9/1 v/v%) to give 31.1 g of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (98%).

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; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H3BrN2

General procedure: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

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 56423-63-3.

Reference:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

l-Chloro-N,N,2-trimethyl-l-propenylamine (0.042 mL, 0.31 mmol) was added to a solution of 3- { [5-(azetidin- 1 -ylcarbonyl)pyrazin-2-yl]oxy }-5- { [(Ii?)- 1 -methyl-2- (methyloxy)ethyl]oxy}benzoic acid (0.102 g, 0.0.31 mmol) in DCM (3 mL) under argon and stirred at RT for 40 minutes. 2-Amino-5-methylpyrazine (57 mg, 0.52 mmol) and pyridine (0.043 mL, 0.52 mmol) were added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue taken up in ethyl acetate (30 mL), washed with water (2 x 10 mL), a saturated aqueous solution of sodium bicarbonate (10 mL), brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo. The crude material was chromatographed on silica, eluting with a gradient of 60-100% ethyl acetate in isohexane, to give the desired compound as a white foam (86 mg). SUP>1H NMR delta (CDCl3): 1.35 (d, 3H), 2.32 – 2.44 (m, 2H), 2.56 (s, 3H), 3.41 (s, 3H), 3.47 – 3.64 (m, 2H), 4.26 (t, 2H), 4.62 (q, IH), 4.69 (t, 2H), 6.98 (s, IH), 7.29 (s, IH), 7.41 (s, IH), 8.13 (s, IH), 8.35 (s, 2H), 8.86 (s, IH), 9.54 (s, IH); m/z 479 (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; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 75907-74-3, 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. 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

In the reaction flask, 2-hydroxymethyl-3,5,6-trimethylpyrazine (3 g, 0.02 mol) was added, Dissolved in 20 mL of dichloromethane, The ice bath was added dropwise with stirring Thionyl chloride (3 mL, 0.04 mol), Stirring reaction 1.5h TLC monitoring to the reaction is complete, The solvent and the remaining dichlorosulfoxide were evaporated under reduced pressure to give a pale yellow mass 2-chloromethyl-3,5,6-trimethylpyrazine 3.2 g, 20 mL of DMF (N, N-dimethylformamide) was added.

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, (3,5,6-Trimethylpyrazin-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KPC Pharmaceuticals, Inc; song, LI MING; Bai, Fei; Yang, ZHAO XIANG; (15 pag.)CN104341358; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.

Step A Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml). The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97%) of 4-(2-pyrazinyl)benzaldehyde.

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

Reference:
Patent; Zhu, Bin; Marinelli, Brett; Macielag, Mark J.; US2005/250713; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4744-50-7, A common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.

Example-1; Preparation of 3-(5-chloropyridin-2-yI)-carbamoylpyrazine-2-carboxylic acid2-Amino-5-chloro pyridine (171.2 g) was suspended in 800 ml toluene and mixture was heated to 48-52 C. Pyrazine-2,3-dicarboxylic acid anhydride (100 g) was added to the suspension at same temperature. The resulting reaction mixture was stirred for 2 hrs at 48-52 C. The reaction slurry was cooled to 20-25 C and stirred for 30 min. The solid was filtered and washed with 100 ml toluene. The filtered solid was added to a mixture of 1000 ml water and 100 ml cone. HCl at 10-15C. The solid was stirred for 60 min at 10-15 C and filtered. The solid was slurred in 400 ml water, filtered and washed with 100 ml water.The solid was dried at 60-70 C to yield 17O g of title compound.

The synthetic route of 4744-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MATRIX LABORATORIES LTD; WO2008/126105; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, 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 56423-63-3, Recommanded Product: 56423-63-3

Under nitrogen protection conditions,(S) -2- amino-3-phenylpropanoic acid (1.6 g, 9.5 mmol), 2-bromopyrazine (1 g, 6.3 mmol) were added sequentially to 50 mL of dry N, N- dimethylacetamide, Potassium carbonate (1.7 g, 12.6 mmol) and cuprous iodide (0.2 g, 0.9 mmol) were added and the temperature was raised to 90 C with stirring.After 48 hours the TLC test showed the reaction was complete and the reaction was allowed to cool to room temperature. 30 mL of ethyl acetate and 10 mL of water were added and the temperature was lowered to 0 C. The pH was adjusted to 3 with 6 M HCl solution. The organic phase was separated and the aqueous phaseThe organic phase was combined, dried over anhydrous sodium sulfate and filtered after drying. The residue was purified by column chromatography on a rotary evaporator (petroleum ether: ethyl acetate = 1: 1) Product 0.7g, yield 46%.

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

Reference:
Patent; Fudan University; Shao Liming; Xu Yulong; Chen Yiyi; Li Wei; Xie Qiong; (25 pag.)CN107151254; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 681249-57-0, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, molecular formula is C6H7F3N4, 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. SDS of cas: 681249-57-0

To the CH2Cl2 solution of 4-(4-(bromomethyl)benzyloxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (0.13 g, 0.284 mmol) was added 2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (0.060 g, 0.313 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.152 ml, 0.853 mmol). The mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and CH2Cl2 (10 mL) and extracted. The organic layer was concentrated and the resulted oil was purified on silica gel column eluted with MeOH and CH2Cl2 to give 2-(2,6-dioxo-piperidin-3-yl)-4-[4-(2-trifluoromethyl-5,6,8,8a-tetrahydro-1H-[1,2,4]triazolo[1,5-a]pyrazin-7-ylmethyl)-benzyloxy]-isoindole-1,3-dione as a white solid (120 mg, 74%). Melting point: 128-130 C. LC-MS m/e=569. HPLC Waters Symmetry C-18, 3.9¡Á150 mm, 5 micro, 1 mL/min, 240 nm, isocratic 50/50 CH3CN/0.1% H3PO4 in H2O=3.64 min (99%); 1H NMR (DMSO-d6) delta 1.94-2.12 (m, 1H, CHH), 2.41-2.47 (m, 1H, CHH), 2.54-2.67 (m, 1H, CHH), 2.77-2.95 (m, 1H, CHH), 3.01 (t, J=5.4 Hz, 2H, CH2), 3.81 (d, J=7.6 Hz, 4H, CH2, CH2), 4.24 (t, J=5.1 Hz, 2H, CH2), 5.09 (dd, J=5.4, 12.7 Hz, 1H, NCH), 5.37 (s, 2H, CH2), 7.37-7.55 (m, 5H, Ar), 7.61 (d, J=8.5 Hz, 1H, Ar), 7.76-7.88 (m, 1H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) delta 21.95, 30.90, 46.54, 47.67, 48.73, 49.21, 59.42, 69.89, 115.53, 116.59, 120.21, 127.42, 128.95, 133.26, 135.25, 136.99, 137.06, 152.84, 155.50, 165.29, 166.75, 169.87, 172.71. Anal Calcd for C27H23F3N6O5+0.5 H2O+0.2 Et2O: C, 56.37%; H, 4.42%; N, 14.19%; Found C, 56.27%; H, 4.20%; N, 14.05%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 681249-57-0, its application will become more common.

Reference:
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 3-AMINO-2-PYRAZINE-CARBOXYLATE (10 g, 65.3 mmol) was dissolved in glacial acetic acid (50 mL) by warming to approximately 45oC. To the warm solution was added bromine (3-7 MOL) in acetic acid (5 mL) dropwise and the resulting mixture was stirred at room temperature for 20 minutes. The solution was diluted with water (300 ML) and then stirred at room temperature for 30 minutes, which resulted in a precipitate. The precipitate was then filtered, washed with water and dried to afford methyl 3-AMINO-6-BROMO-2-PYRAZINE-CARBOXYLATE as a yellow solid (14. 2 g, 94 percent). IH NMR (300 MHz, CDC13) 63. 99 (s, 3 H), 8.30 (s, 1 H) ; 13C NMR (100 MHZ, CDC13) A 53.02, 123.49, 124.85, 150.24, 154.70, 166.04.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-aminopyrazine-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2004/92177; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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, Product Details of 19745-07-4

N-ethyl piperidin-4-ol(200 mg1.55 mmol) was added to dry THF (10 mL) and the mixture was cooled to 0oC, then NaH (60percent, 124 mg3.1 mmol) was added slowly. The mixture was stirred at 0oC for 0.5 h and then 2,5-dichloropyrodazine(231 mg1.55 mmol) was added and stirred overnight. The reaction was quenched with iced water and extracted with DCM, the organic layer was washed with brine, dried and concentrated to afford compound 12(330 mg, white solid).LC-MS: 242.1(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, 2,5-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fu, Yan; Tang, Shuai; Su, Yi; Lan, Xiaojing; Ye, Yan; Zha, Chuantao; Li, Lei; Cao, Jianhua; Chen, Yi; Jiang, Lei; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5332 – 5336;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem