Tag: M.W=100-200

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

Preparation 21-Pyrazin-2-yl-ethylamineThe synthetic procedure used in this preparation is outlined below in Scheme C. To a solution of 1-pyrazin-2-yl-ethanone (2.0 g, 15.85 mmol) and ammonium acetate (19.337 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dichloromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 14.62 g of 1-pyrazin-2-yl-ethylamine, yield: 75%. MS (M+H)=124.

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

Reference:
Patent; Dillon, Michael Patrick; Krauss, Nancy Elisabeth; US2010/324070; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23688-89-3, 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 23688-89-3 as follows.

Intermediate 13 was prepared from the indicated bromide and boronic acid by methods analogous to those described for Intermediate 12.:_To a solution of ethyl 2-ethoxy-4-(4,4, 5, 5-tetramethyl- 1, 3,2-dioxaborolan-2- yl)benzoate (439 mg, 1.37 mmol) and 6-bromo-5-fluoropicolinic acid (302 mg, 1.37 mmol) in 1,4-dioxane (6.9 ml) was added a solution of sodium carbonate (436 mg, 4.11 mmol) in water (2 ml). The reaction was purged with nitrogen and PdCI2(dppf)-CH2CI2 adduct (112 mg, 0.14 mmol) was added and the reaction then heated at 80 00 for 18 hours. The reactionwas then cooled to room temperature and concentrated. The residue was partitioned between water and EtOAc and the aqueous phase acidified. The layers were separated, and the aqueous phase was extracted with further EtOAc (3 x 20 ml). The combined organic extracts were dried over Mg504, filtered, and concentrated to give the title compound as an orange solid (129 mg, 28 % yield).

According to the analysis of related databases, 23688-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (274 pag.)WO2017/6295; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 27398-39-6, A common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

9.3 3-Chloro-pyrazine-2-carboxylic acid[1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-amide; Under an atmosphere of nitrogen, 3-chloro-2-pyrazinecarboxylic acid (Tyger, 250 mg), TBTU (532 mg), and diisopropylethylamine (1.34 ml) were added to a solution of 2-(2-naphthalen-2-yl-ethoxy)-acetamidine hydrochloride (417 mg) in DMF (5 ml). The reaction mixture was stirred for 2 h at r.t., diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The obtained, crude title compound (567 mg) was used without further purification in the next step.

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conte, Aurelia; Dehmlow, Henrietta; Grether, Uwe; Kratochwil, Nicole A.; Kuehne, Holger; Narquizian, Robert; Panousis, Constantinos G.; Peters, Jens-Uwe; Ricklin, Fabienne; US2008/234277; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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 297172-19-1, SDS of cas: 297172-19-1

General procedure: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 8 (100 mumol, 1.0 equiv) and compound 9 (150 mumol, 1.5 equiv) in DMF (0.1 M) was treated with K2CO3 (300 mumol, 3.0 equiv) and stirred at 110 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 10. The crude aldehyde 10 (100 mumol, 1.0 equiv) was dissolved in acetone:water (2:1, 0.1 M) and treated with KMnO4 (600 mumol, 6 equiv) and stirred at 30 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 11. The crude acid 11 (100 mumol, 1.0 equiv) was treated with HATU (120 mumol, 1.20 equiv) followed by the crude amine (100 mumol, 1.0 equiv) and NEt3 (300 mumol, 3.0 equiv). The reaction was stirred at 30 C for 16 h (LCMS check). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile-water (0.225% formic acid or pH = 10 NH4OH) gradient. All compounds were deemed greater than 95% purity by LCMS and HPLC.

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, 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Londregan, Allyn T.; Piotrowski, David W.; Futatsugi, Kentaro; Warmus, Joseph S.; Boehm, Markus; Carpino, Philip A.; Chin, Janice E.; Janssen, Ann M.; Roush, Nicole S.; Buxton, Joanne; Hinchey, Terri; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1407 – 1411;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 63286-28-2, The chemical industry reduces the impact on the environment during synthesis 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, I believe this compound will play a more active role in future production and life.

2-Chloro-3-hydrazinylpyrazine C-1 (15.6 g; 108 mmol) is slurried up in (300 ml) THF and cooled down in an ice bath to -5 C. Trifluoroacetic anhydride (17 ml; 118 mmol) is also dissolved in 300 ml THF and dropped slowly to the first solution. After 1 h most of the THF is evaporated, than a small amount of water is added and the mixture is extracted with DCM. The organic phase is dried over MgSO4 and evaporated to dryness. Yield: 100% HPLC-MS: (M+H)+=241/243; tRet=1.31 min; method FSUN2

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-Chloro-3-hydrazinylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENGELHARDT, Harald; US2015/133447; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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. Computed Properties of C5H4N4

[0120] 5-chloro-2-methoxybenzoic acid (370.0 mg, 1.981 mmol) was dissolved in THF (10.0 mL), followed by the addition of catalytic amount of DMF (20 .iL) and oxalyl chloride (0.20 mL, 2.377 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo, and the residue was re-dissolved in THF (10.0 mL). In another flask, 5-aminopyrazine-2- carbonitrile (170.0 mg, 1.415 mmol) was dissolved in THF (5.0 mL) followed by addition of NaH (85.0 mg, 2.123 mmol, 60% in mineral oil). The mixture was stirred for 10 minutes before it was added to the flask containing the freshly prepared acid chloride dropwise at rt. The reaction was stirred at rt for 30 mm before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-methoxybenzamide (40.0 mg, 10% yield) which was mixed with pyridinium chloride (550.0 mg). The mixture was heated to 200 C, stirred for 10 minutes and cooled down to rt. The resulting solid was dissolved in water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-hydroxybenzamide 3 (27.5 mg, 72% yield). ?H NMR (300 MHz, Acetone-d6) 6 9.70 (d, J= 1.5 Hz, 1H), 8.90 (d, J= 1.5 Hz, 1H), 8.16 (d, J= 2.7 Hz, 1H), 7.59 – 7.51 (m, 1H), 7.17 (d, J= 8.8 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C12H8C1N402) requires m/z 275.0, found m/z 275.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113305-94-5, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; JIN, Shengkan; AUGERI, David, J.; KIMBALL, David, S.; LIU, Peng; TAO, Hanlin; ZENG, Xiangang; (82 pag.)WO2016/81599; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]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 875781-43-4, Formula: C6H4BrN3

Step 1To a partial suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) in 1,4- dioxane (100 mL) was added 2.0 M aqueous NaOH (25 mL, 50.0 mmol) and 37% aqueous formaldehyde (19 mL, 252 mmol). The dark homogenous reaction mixture was stirred at room temperature overnight. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HC1 and extracted with EtOAc (2x). The combined organics were concentrated to afford 2.6 g of an orange solid. Upon standing, a thick brown precipitate formed in the aqueous layer. The precipitate was collected by filtration and dried. The brown solid was extracted with hot 10% MeOH/EtOAc (3 x 200 mL). The extracts were combined and evaporated to provide an additional 3.05 g of orange solid. Overall yield was 5.65 g (87%) of (2-bromo-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin- 5-yl)-methanol.

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; F. HOFFMANN-LA ROCHE AG; HENDRICKS, Robert Than; HERMANN, Johannes Cornelius; KONDRU, Rama K.; LOU, Yan; LYNCH, Stephen M.; OWENS, Timothy D.; SOTH, Michael; YEE, Calvin Wesley; WO2011/144584; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 399-66-6, 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. 399-66-6, name is [1,2,4]Triazolo[1,5-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Stage 4. Platinum (IV) oxide (2.75 g, 12.1 mmole) was added to a suspension, saturated with nitrogen, of CaO (9.30 g, 166 mmole) and [ 1, 2 , 4 ] -triazolo [ 1, 5-a] pyrazine (18.1 g, 151 mmole) in methoxyethanol (150 ml) . The reaction mixture was stirred for 21.5 hours under a hydrogen atmosphere. The catalyst was filtered off through filter earth and washed with DCM/ethanol (9:1). The filtrate was concentrated, and the solvent was removed firstly with toluene and then with 2-propanol. The residue was taken up in ethyl acetate, filtered again through filter earth, washed with ethyl acetate, and concentrated. The residue was washed with hot 2-propanol and concentrated in vacuo.

The chemical industry reduces the impact on the environment during synthesis [1,2,4]Triazolo[1,5-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 313339-92-3, A common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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.

3,5-Dichloropyrazine-2-carbonitrile (Example 12, Step 2, 31.0 g, 178.18 mmol) was dissolved in anhydrous diethyl ether (890 mL, 0.2M) and cooled to -78 C. Then MeMgBr in diethyl ether (3.0 M, 65.33 mL, 190.0 mmol) was added slowly to maintain low temperature. After the addition was complete, the mixture was slowly warmed room temperature and stirred 1 h. The mixture was poured into a beaker containing a mixture of HCl in water (1.0 M, 1 L) and ice (1 kg). The mixture was stirred vigorously for 10 min. The mixture was extracted with diethyl ether (3*1 L), the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as an orange oil (34 g, 99% yield). The mixture was used for the next reaction without further purification.

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLX Bio, Inc.; Beck, Hilary Plake; Biannic, Berenger; Bui, Minna Hue Thanh; Hu, Dennis X.; Jackson, Jeffrey J.; Ketcham, John Michael; Powers, Jay Patrick; Reilly, Maureen Kay; Robles-Resendiz, Omar; Shunatona, Hunter Paul; Walker, James Ross; Wustrow, David Juergen; Younai, Ashkaan; Zibinsky, Mikhail; (339 pag.)US2018/72743; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89464-87-9, name is 3-Methoxy-5-methylpyrazin-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 89464-87-9, Formula: C6H9N3O

3-methoxy-5-methylpyrazin-2-amine (0.33 g) and the product of Example 1, step (a) were subjected to the procedure described in Example 1, step (b) to afford the product as a pale yellow solid (0.68 g).m/e 389 (M+l)+, 100%.JH NMR (CDC13) 8 7.8 (1H, br), 7.58 (1H, br), 4.01 (3H, s), 2.35 (3H, s).MP 146-147C.Elemental Analysis:Theory: C 30.90, H 2.07, N 10.81 %Found: C 31.12, H 2.00, N 10.79 %

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-5-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2004/108717; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem