Tag: M.W=100-200

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. 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

To a solution of octahydropyrido[1,2-a]pyrazine (50 mg, 0.38 mmol) and NEt3 (83 muL, 0.59 mmol) in DCM (15 mL) at 0 C. was added a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonyl chloride from Example 121 (93 mg, 0.12 mmol) in DCM (5 mL) and the resulting mixture warmed to RT after 10 min then stirred for 1 h. The reaction mixture was diluted with DCM, washed with a saturated aqueous NaHCO3 solution then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in EtOAc) then freeze-dried from MeCN/H2O affording 132 (36 mg, 62%) as a white solid. LCMS: RT 2.90 min [M+H]+ 498.3. 1H NMR (DMSO, 400 MHz): delta 8.78 (1H, d, J=2.41 Hz), 8.01 (1H, s), 7.94 (1H, s), 7.63 (1H, dd, J=8.63, 2.42 Hz), 7.28 (1H, d, J=8.62 Hz), 5.73-5.72 (1H, m), 4.63-4.59 (4H, m), 3.53 (1H, d, J=11.02 Hz), 3.43 (1H, d, J=9.07 Hz), 2.70-2.68 (2H, m), 2.33-2.32 (1H, m), 2.19-2.11 (1H, m), 1.93-1.92 (3H, m), 1.62 (1H, d, J=12.59 Hz), 1.57-1.52 (2H, m), 1.49 (6H, t, J=6.30 Hz), 1.38-1.16 (2H, m), 1.01-0.87 (1H, m)

The synthetic route of 4430-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; US2012/245144; (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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

5-Bromo-lH-pyrrolo [2,3-b] pyrazine (59.4 g & ‘ 0.3 was added in the reactor Methyl-N-(1-(4-methylpiperazin-1-yl) -2,3-dihydro-1 // – Inden-5-yl) -benzamide(112 mg, 0.3 Mmol), bistriphenylphosphine dioxane 1 E (22 mg & ‘ 0.03 mmol), tricyclic Hexylphosphine (16 mg, 0.06 mmol), cuprous iodide carbonate (99 mg, 0 3 mmol), 6 drops of N, N-diisopropyl Ethylamine was added, and at the end of reaction Kh ‘at 80 C, ethyl acetate and aqueous ammonia were added And washed with saturated NaCl solution, dried over anhydrous Na2S04, filtered, Dried, and purified by column chromatography to give the title compound

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

Methyl 2-amino-3-pyrazine carboxylate (2. 2 g) was dissolved in dry DCM (20 ml) to give a cloudy pale yellow solution, and pyridine (2 ml) in dry DCM (12 ml) was added. The stirred suspension was cooled in an ice bath, and 2,4, 6-trifluorophenylacetyl chloride (3.0 g) in dry DCM (13 ml) was added dropwise. The reaction gradually became a deep orange, and then went clear. It was stirred for 6 hours and stood overnight. The reaction mixture was washed with water, brine, and then dilute hydrochloric acid, and the DCM layer was dried over magnesium sulphate. The solvent was evaporated to yield an orange solid which was triturated with ether, to give methyl 2- [2, 4, 6-TRIFLUOROPHENYLACETYLAMINO]-3-PYRAZINE carboxylate as a yellow solid (1.5 g). LH NM : R (CDC13) 8 ppm: 4.03 (s, 5H), 6.74 (t, 2H), 8.43 (d, LH), 8.61 (d, LH) 10.9 (s, LH).

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WO2004/56825; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6164-79-0, The chemical industry reduces the impact on the environment during synthesis 6164-79-0, name is Methyl 2-pyrazinecarboxylate, I believe this compound will play a more active role in future production and life.

(1) Pyrazine-2-carboxylic acid is fully dissolved in anhydrous methanol,Then add an appropriate amount of concentrated sulfuric acid and heat to reflux for 5 h.After the reaction is cooled, adjust the pH to neutral with saturated NaHCO3,Extract with dichloromethane and keep the dichloromethane layer,The solvent was removed by rotary evaporation to obtain an oily pyrazine-2-carboxylic acid methyl ester;After dissolving it in anhydrous methanol, hydrazine hydrate was added dropwise, and after heating under reflux for 21 h,Cool to room temperature, remove methanol by rotary evaporation to obtain pyrazine-2-hydrazide as a red solid product;The ratio of the amount of pyrazine-2-carboxylic acid methyl ester to the amount of hydrazine hydrate is 1: 2.

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, Methyl 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tianjin Medical University; Xu Jingyuan; Wang Zhigang; Xie Chengzhi; (13 pag.)CN110372681; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-Chloropyrazine, 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 14508-49-7, category: Pyrazines

The product of preparation 16 (83mg, 0.32mmol), 2-chloropyrazine (36mg, 0.31 mmol), sodium tert-butoxide, (36mg, 0.37mmol), Pd2(dba)3 (7mg, 8mumol) and BINAP (22mg, 35mumol) were suspended in tert-butanol (2mL) and the mixture was heated at 110C in the microwave for 3 hours. The mixture was replenished with further amounts of 2-chloropyrazine (36mg, 0.31 mmol), sodium tert-butoxide (36mg, 0.37mmol), Pd2(dba)3 (7mg, 8mumol) and BINAP (22mg, 30mumol) at hourly intervals. The reaction mixture was then azeotroped with methanol and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:methanol: 0.88 ammonia, 100:0:0 to 90:10:1. This was followed by further purification by column chromatography on Biotage amino silica gel, eluting with pentane:ethyl acetate, 100:0 to 0:100, to afford the title compound as a colourless oil in 76% yield, 80mg. 1HNMR(CDCl3, 400MHz) delta: 1.70-1.90(m, 4H), 1.91-2.04(m, 2H), 2.47-2.63(m, 6H), 2.93-3.02(m, 2H), 3.90-3.98(m, 2H) 4.28-4.35(m, 2H), 4.63(s, 2H), 6.60(d, 1H), 7.37(d, 1H), 7.85(m, 1H), 8.10(m, 1H), 8.21(m,1H) MS APCI+ m/z 340 [MH]+ Micro analysis found (%); C(67.21), H(7.46), N(20.60); C19H25N5NO requires (%); C(67.31), H(7.42), N(20.63)

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; Pfizer Limited; EP1595881; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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 36070-75-4, COA of Formula: C5H2ClN3

1-((2S,4/?)-4-amino-6-bromo-2-methyl-3,4-dihydroquinolin-1 (2/-/)-yl)ethanone (for a preparation, see Intermediate 1 ) (50 mg, 0.177 mmol), 5-chloropyrazine-2-carbonitrile (37.0 mg, 0.265 mmol) and DIPEA (0.123 mL, 0.706 mmol) were combined in NMP (1 .5 mL) and heated in a sealed flask under microwave irradiation to 200C for 1 h. The mixture was partitioned between water (150 mL) and EtOAc (4×100 mL). The organic layers were combined, washed with brine (2×100 mL), dried by passing through a hydrophobic frit, and concentrated in vacuo. The resulting residue was purified by chromatography (25 g column, EtOAc/cyclohexane gradient) to give 5-(((2S,4/?)-1-acetyl- 6-bromo-2-methyl-1 ,2,3,4-tetrahydroquinolin-4-yl)amino)pyrazine-2-carbonitrile (61 mg, 0.158 mmol, 89 % yield) as a brown gum.LCMS (Formate, 2 min), Rt = 0.94 mins, MH+ = 386/388.

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, 5-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; DEMONT, Emmanuel Hubert; MITCHELL, Darren Jason; SEAL, Jonathan Thomas; WO2012/143415; (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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, A new synthetic method of this compound is introduced below., name: 1-(3-Ethylpyrazin-2-yl)ethanone

(1) 2-acetyl-3-ethylpyrazine (420 ul, 3 mmol) was dissolved in methanol (20 ml).After dissolution,Add 4,4-dimethyl-3-thiosemicarbazide (360 mg, 3 mmol),well mixed,The mixed solution was refluxed at 65 C for 4 h.filter,The filtrate is volatilized at room temperature.There are pale yellow crystals,Filter again,Wash 2-3 times with absolute ethanol,Obtaining a ligand L4;

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; Guangxi Normal University; Yang Feng; Sun Zewen; Zhao Lei; Liang Hong; (16 pag.)CN109796501; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 23611-75-8, 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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 15; 6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-m-tolylpyrazine-2-carboxamide; Example 15A; 6-chloropyrazine-2-carboxylic Acid; The product from Example 1E (1.78 g, 10.3 mmol) was dissolved in EtOH (25 mL). 1M NaOH (25 mL) was added, and the reaction stirred at ambient temperature for 2 h. The reaction mixture was acidified to pH?3 with 1M HCl (aq). The mixture was then diluted with water (150 mL) and extracted with EtOAc (4×100 mL). The organic extracts were combined, washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under vacuum to provide the title compound as a white solid (1.54 g, 94%). MS (DCI/NH3) m/z 176 (M+NH4)+.

The synthetic route of Methyl 6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US2009/281118; (2009); 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4N4

To a suspension of 5-aminopyrazine-2-carbonitrile (414 mg, 3.44 mmol) in THF (10 mL) was added sodium hydride (230 mg, 5.73 mmol) at 0 C and the resulting mixture was then stirred at ambient temperature for 1 h. Compound 305-4 (1.0 g, 2.87 mmol) was added and stirred at 60 C for 4 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated to afford the title compound 306-4 as a yellow solid (500 mg, 42% yield). LCMS:420.9 [M+1]. ?H NIVIR (400 1VIFIz, DMSO-d6): 2.36 (s, 3H), 3.35 (s, 3H), 3.77 (s, 3H), 5.21 (s, 2H), 5.68 (s, 1H), 6.86-6.88 (m, 2H), 8.63 (d, J 1.2 Hz, 1H), 8.86 (d, J1.2 Hz, 1H), 13.89 (s, 1H).

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; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H3ClN2O2

Preparation of (5-chloropyrazin-2-yl)(pyrrolidin-1-yl)methanone (SM-1):(SM-1 ) delta-chloropyrazine^-carboxylic acid (1 .00 gram, 6.31 mmol) in dichloromethane (30 ml_) was treated with catalytic amount of dimethylformamide, followed by (COCI)2 (0.85 ml_, 9.46 mmol). The resulting mixture was stirred over night. The reaction was concentrated and dried under vacuum to give desired delta-chloropyrazine^-carbonyl chloride as a solid (1 .05 g, 100%). delta-chloropyrazine^-carbonyl chloride (670mg, 3.79mmol) was dissolved in dichloromethane (1 OmL) and cooled to O0C. Thethylamine (1 .58ml_, 1 1 .4mmol) and pyrrolidine (0.32ml_, 3.79mmol) were then added successively drop-wise. Following the addition, the ice bath was removed and the reaction was allowed to warm to room temperature and stir for 1 hour. The reaction was then diluted with dichloromethane and washed with 1 N HCI, water, and brine. The organics were dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography eluting with 30 – 80% ethyl acetate in hexane afforded the desired (5-chloropyrazin- 2-yl)(pyrrolidin-1 -yl)methanone (SM-1 : 677.0mg, 84.5%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1 .86 – 1 .99 (m, 4 H),3.65 – 3.71 (m, 2 H), 3.73 – 3.79 (m, 2 H), 8.52 (d, J=1 .37 Hz, 1 H), 8.93 (d, J=1 .37 Hz, 1 H).

The synthetic route of 36070-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; CORBETT, Jeffrey Wayne; GUZMAN-PEREZ, Angel; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/103438; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem