Month: May 2021

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

To a solution of l-oxooctahydropyrido[l,2-c][l,3]oxazine-7-carboxylic acid (3.13 g, 15.7 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl)methanamine hydrochloride (2.8 g, 15.7 mmol), TEA (4.8 g, 47.2 mmol) and HATU (6 g, 15.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was complete detected by LCMS. The reaction mixture was treated with DCM and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with DCM/THF = 5/1 to give N-((3-chloropyrazin-2-yl)methyl)-l- oxooctahydropyrido[l,2-c][l,3]oxazine-7-carboxamide (4.7 g, 92%).1H- NMR(CDC13,400 MHz) delta 1.40 – 1.49 (m, 1 H), 1.71 – 1.92 (m, 3 H), 2.04 – 2.26 (m, 2 H), 2.43 – 2.57 (m, 1 H), 2.81 – 2.97 (m, 1 H), 3.31 – 3.42 (m, 1 H), 4.13 – 4.27 (m, 2 H), 4.46 – 4.56 (m, 1 H), 4.64 (d, /= 4.70 Hz, 2 H), 8.29 (d, /= 2.35 Hz, 1 H), 8.44 (d, /= 2.35 Hz, 1 H).

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4, The chemical industry reduces the impact on the environment during synthesis 33332-28-4, name is 2-Amino-6-chloropyrazine, I believe this compound will play a more active role in future production and life.

(c) N-(6-Chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide This compound was prepared from 4-hydroxy-2-methyl-N-ethyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide, 2-amino-6-chloro-pyrazine and p-toluenesulfonic acid analogous to Example 14. Yield: 68percent of theory. Melting point: 278°-279° C. (decomposition). C14 H11 ClN4 O4 S (366.79): Calc.: C–45.84percent; H–3.03percent; Cl–9.67percent; N–15.28percent; S–8.74percent. Found: C–45.62percent; H–3.11percent; Cl–9.70percent; N–15.04percent; S–8.59percent.

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-Amino-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, 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 109-08-0, Product Details of 109-08-0

EXAMPLE 27 2-(hept-6-enyl)pyrazine (Compound ID 57) Methylpyrazine (940 mg, 912 10 mmol) was added to sodium amide (490 mg, 12.5 mmol) in 10 ml liquid NH3 at -65° C. and the red mixture was stirred for 30 min. A solution of 1-bromohex-5-ene (7.5 mmol) in dry ether was added dropwise and the mixture was stirred for another hour. The reaction was quenched by addition of ammonium chloride (626 mg, 11.7 mmol) and NH3 was evaporated by heating at ether reflux. The ether was removed and the residue extracted several times with ether. The combined ether phases were washed with water, dried over sodium sulfate, evaporated under vacuum and purified by FC (hexane/ethyl acetate 1/1). 2-(hept-6-enyl)pyrazine was isolated as a GC-pure oil (1.03 g, 78percent). Rf 0.52 (hexane/ethyl acetate 1/1). 1H-NMR (400 MHz, CDCl3): 8.48 (s, 1H); 8.45 (s, 1H); 8.39 (s, 1H); 5.78 (m, 1H); 5.00-4.94 (m, 2H); 2.81 (t, J=7 Hz, 2H); 2.04 (m, 2H); 1.75 (m, 2H); 1.41 (m, 4H). 13C-NMR (CDCl3): 158.29; 144.96; 144.34; 142.46; 139.22; 114.82; 35.81; 33.99; 29.65; 29.12; 29.03. GC-MS: 16.23 min, m/z 176.

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

Reference:
Patent; Givaudan SA; US2010/113460; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 109838-85-9, The chemical industry reduces the impact on the environment during synthesis 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, I believe this compound will play a more active role in future production and life.

The starting material, methyl 3-{6-[3-(5,6,7,8-tetrahydro-l,8-naphthyridin-2- yl)propyl]pyridin-3-yl}-L-alaninate was prepared as follows: To a solution of (2i?)-2-isopropyl-3,6-dimethoxy-2,5~dihydropyrazine (5 ml, 27.9 mmol) in THF (130 ml) was added at -78°C 1.6 M nBuLi (17.44 ml, 27.9 mmol). The mixture was stirred at -78°C for 10 min and treated with a solution of 2,5-dibromopyridine (7 g, 27.9 mmol) in THF ( 2 ml). After stirring for 2 hours, H2O ( 100 ml) was added and the mixture was allowed to warm up to ambient temperature. After extraction with ether and evaporation, the residue was purified by silica gel chromatography (10percent to 30percent ethyl acetate in petroleum ether) to afford (25r,5i?)-2-[(6-bromopyridin-3-yl)methyl]-5-isopropyl- 3,6-dimethoxy-2,5-dihydropyrazine (8.2g, 83percent); 1H NMR Spectrum:fDMSOd6) 0.58 (d, 3H), 0.92 (d, 3H), 2.06-2.15 (m, IH), 2.97 (dd, IH), 3.04 (dd, IH), 3.50 (t, IH), 3.61 (s, 3H), 3.66 (s, 3H), 3.34-3.39 (m, IH), 7.47 (dd, IH), 7.54 (d, IH), 8.11 (d, IH).

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, (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/93065; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 957344-74-0,Some common heterocyclic compound, 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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 2 (5-Bromo-imidazo[l,2-a]pyrazin-8-yl)-[4-(l-methyl-piperidin-4-ylmethoxy)-phenyl] -amine[00319] To a solution of 5,8-dibromo-imidazo[l,2-a]pyrazme (0.100g, 0.36mmol) in isopropanol (5mL) are added l,4-diazabicyclo[2,2,2]octane (DABCO) (0.036mL, 0 36mmol) and 4-(l- methyl-pipe?dm-4-ylmethoxy)-phenylamme (79 6mg, 0 36mmol) The reaction mixture is stirred at9O0C overnight The solvent is evaporated and the residue chromatographed on silica gel column elutmg with 97 3 followed by 94 6 and 90 10 DCM MeOH The title compound is obtained as a solid(20mg, 13%) LCMS Rt 2 30mm (94%), m/z (APCI) 417

The synthetic route of 957344-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-58-4, 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. 5521-58-4 name is 5-Methylpyrazin-2-amine, 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.

Example 22; Synthesis of N-(5-methyl-pyrazin-2-yl l)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide; Step 1; Phenyl 5-methylpyrazin-2-ylcarbamate; 2-Amino-5-methyl-pyrazine (2.00 g, 21.25 mmol) was dissolved in THF (80 mL), cooled to 0 C., and treated with pyridine (1.77 g, 22.3 mmol) followed by the dropwise addition of phenylchloroformate (3.49 g, 22.3 mmol) in THF (30 mL). After stirring for 3 h, 100 mL of MeCN was added and the reaction mixture was reduced to a volume of 100 mL in vacuo. The title compound as white crystals was collected by filtration (2.5 g, 55%) and was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; FAY, Lorraine Kathleen; Johnson, Douglas S.; Kesten, Suzanne Ross; Lazerwith, Scott E.; Morris, Mark Anthony; Stiff, Cory Michael; Meyers, Marvin Jay; Wang, Lijuan Jane; US2008/261941; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, 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 957230-70-5, Recommanded Product: 3,6-Dibromopyrazin-2-amine

3,6-dibromopyrazin-2-ylamine (4.0 g, 15.80 mmol) and bromoacetaldehyde diethyl acetal (3.7 mL, 24.00mmol) and tetrahydrofuran (5.3 mL) eere dissolved in distilled water (53 mL), the mixture was stirred for 4 hours at 120C .Saturated aqueous sodium hydrogen carbonate solution to the reaction solution was neutralized by addition. The resulting solid was filtered and washed with distilled water and dried to give the title compound (2.75 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dibromopyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; HANMI PHARM. CO., LTD.; HAM, YOUNG JIN; SON, JUNG BEOM; PARK, CHANG HEE; KANG, SEOK JONG; CHOI, JAE YUL; KIM, SEO HEE; (36 pag.)KR2015/113801; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, 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 1458-18-0 as follows.

5,6-DICHLORO-3-HYDROXYPYRAZINE-2-CARBOXYLIC ACID (21). Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate (5.0 g, 23 mmol) was stirred in conc. sulfuric acid (140 mL) and cooled to 0 C. Sodium nitrite was added slowly, maintaining the temperature close to 0 C. After an additional 30 minutes at 0 C. the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was poured into 500 g of ice, resulting in bubbling and foaming. After 30 minutes, the mixture was extracted 3 times with EtOAc. The combined organic extract was dried (MgSO4), filtered and concentrated. The yellow solid which was left was washed with water and air-dried, to leave 5.0 g of a yellow solid, m.p. 114-116 C. whose 13C-NMR spectrum was consistent with the methyl ester of the title compound. This solid (5.0 g) was treated with 1N NaOH (20 mL) and the mixture heated at 90 C. for 1.5 hours. After allowing to cool, the mixture was acidified with conc. HCl, then extracted 3 times with EtOAc. Drying (MgSO4), filtration and concentration afforded 0.48 g of a dark yellow solid, whose 1H-NMR and MS spectra were consistent with the title acid 21.

According to the analysis of related databases, 1458-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; US6355660; (2002); B1;,
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. 33332-29-5, name is 2-Amino-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 33332-29-5

5-CHLORO-2-PYRAZINAMINE (D47, Step 1) (2.41 g, 18.6 MMOL) was dissolved in concentrated hydrochloric acid (24 ML), cooled in an ice-acetone bath and treated with a solution of sodium nitrite (2.63 g, 38.1 MMOL) in water (18 ML) dropwise over a period of 1 hour. The mixture was cooled in an ice-water bath and left to stir for 1 hour. The mixture was allowed to warm to room temperature over 1 hour, neutralised by addition of sodium hydroxide solution (2M) and extracted with dichloromethane. The DICHLOROMETHANE layers were combined, dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate: pentane (1: 9) to afford the title compound (0.33 g);’H NMR (CDCI3) 8.40 (2H, s).

According to the analysis of related databases, 33332-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 16298-03-6,Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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.

(A) Methyl 2-bromo-3-pyrazine carboxylate To a stirred mixture of 12.7 g. of methyl 2-amino pyrazine 3-carboxylate and 47 ml. of 48% hydrobromic acid there is added, dropwise, 12.6 ml. of bromine keeping the temperature at 0. A solution of 14.4 g. of sodium nitrite in 60 ml. of water is then added, dropwise, at 0 and the reaction mixture stirred for 15 minutes. The reaction mixture is basified to pH 8 with sodium bicarbonate and extracted with ethyl acetate and again with chloroform. The organic layers are dried over magnesium sulfate, filtered and concentrated to a yellow oil. Recrystallization from ether-hexane yields the product, m.p. 43-45 C.

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-aminopyrazine-3-carboxylate, its application will become more common.

Reference:
Patent; Schering Corporation; US4492702; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem