Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-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 313339-92-3, Recommanded Product: 3,5-Dichloropyrazine-2-carbonitrile

Example 34 5-(1-carbamoylcyclobutylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide A solution of 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.574 mmol), 1-aminocyclobutanecarboxamide hydrochloride (108 mg, 0.717 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 70 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(6-chloro-5-cyanopyrazin-2-ylamino)cyclobutanecarboxamide (22 mg).

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; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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. Application In Synthesis of 3,5-Dichloropyrazine-2-carbonitrile

To a solution of 44 3,5-dichloropyrazine-2-carbonitrile (3) (120mg, 0.69mmol) in 45 formamide (5.3g, 120mmol) were added 46 H2SO4 (37muL, 0.69mmol), FeSO4·7H2O (190mg, 0.69mmol) in 47 H2O (700muL) and 48 H2O2 (230muL, 2.1mmol) in H2O (700muL) dropwise at 0C, and the mixture was stirred at the same temperature for 30min. The reaction mixture was quenched with 49 ice water and extracted with EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to give 7 4 (99mg, 66%) as a pale yellow solid. 1H NMR (DMSO-d6) delta ppm 8.18 (1H, br s), 8.28 (1H, br s); MS (ESI) m/z 197, 199 [M-HCl+H2O]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 313339-92-3, its application will become more common.

Reference:
Article; Kunikawa, Shigeki; Tanaka, Akira; Takasuna, Yuji; Tasaki, Mamoru; Chida, Noboru; Bioorganic and Medicinal Chemistry; vol. 26; 20; (2018); p. 5499 – 5509;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 72788-94-4,Some common heterocyclic compound, 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, molecular formula is C5H5ClN2O, 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 stirred solution of (5-chloropyrazin-2-yl)methanol (0.50 g, 3.46 mmol) in DCM (10 mL) was added imidazole (0.94 g, 13.84 mmol) followed by TBDMS-Cl (1.04 g, 6.92 mmol) and stirring continued at ambient temperature for 12 h. The resulting reaction mixture was diluted with water (40 mL) and extracted with DCM (2 x 40 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-24 g, 5- 10 % EtOAc/n-hexane) to obtain Intermediate 103A (0.85 g, 89.00%). 1H NMR (400 MHz, DMSO-d6) G ppm 0.11 (s, 6 H), 0.91 (s, 9 H), 4.84 (s, 2 H), 8.50 (s, 1 H), 8.75 (d, J = 1.00 Hz, 1 H). LCMS (Method-D): retention time 3.69 min, [M+H] 259.

The synthetic route of 72788-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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. Computed Properties of C6H9N3

Example 94 N-(5-(5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)pentyl)-5-(thiophen-2-yl)isoxazole-3-carboxamide To a solution of intermediate B (150 mg, 0.54 mmol, 1.0 eq) in CH2ClCH2Cl (10 mL) were added imidazo[1,5-a]pyrazine,5,6,7,8-tetrahydro-(9Cl) (132.7 g, 1.07 mmol, 2.0 eq), NaBH(OAc)3 (685.3 mg, 3.24 mmol, 6.0 eq), acetic acid (97.1 mg, 1.62 mmol, 3.0 eq). Then the mixture was stirred at 15 C. for 12 hours. The mixture was quenched with water (10 mL). The mixture was extracted with DCM. The combined organic phase was concentrated to obtain the crude product which was purified by preparative HPLC (column: Xtimate C18 150*25 mm*5 um, gradient: 33-63% B (A=0.05% ammonia hydroxide/water, B=acetonitrile) to give the title compound (95 mg, 45.7% yield) as a light yellow solid. MS (ESI) m/z 386.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.80 (t, J=5.6 Hz, 1H), 7.86 (dd, J=5.2, 0.8 Hz, 1H), 7.78 (dd, J=4.0, 1.2 Hz, 1H), 7.49 (s, 1H), 7.27-7.25 (m, 1H), 7.16 (s, 1H), 6.61 (s, 1H), 3.97 (t, J=5.6 Hz, 2H), 3.53 (s, 2H), 3.28-3.23 (m, 2H), 2.73 (t, J=5.6 Hz, 2H), 2.45 (t, J=6.8 Hz, 2H), 1.58-1.48 (m, 4H), 1.36-1.30 (m, 2H).

The synthetic route of 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BECKWITH, Rohan Eric John; JIANG, Hua; WANG, Ce; (54 pag.)US2018/271837; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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. Application In Synthesis of Pyrazinoic acid hydrazide

General procedure: Compound 4a or compound 4b (1.0 eq) was dissolved in ethanol (2mL) and then the corresponding amine derivative (1.0 eq) was added. The reaction mixture was stirred at room temperature until the reaction was done (monitored by TLC). The resultant mixture was concentrated under reduced pressure and purified by column chromatography to give the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 768-05-8, its application will become more common.

Reference:
Article; Wang, Shuai; Zhao, Li-Jie; Zheng, Yi-Chao; Shen, Dan-Dan; Miao, Er-Fei; Qiao, Xue-Peng; Zhao, Li-Juan; Liu, Ying; Huang, Ruilei; Yu, Bin; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 940 – 951;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 138588-41-7, 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. 138588-41-7 name is Pyrazine-2-carboximidamide hydrochloride, 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.

To a solution of Example 1G (0.750 g, 2.28 mmol) in isopropanol (20 mL) was added pyrazine-2-carboximidamide hydrochloride (1.09 g, 6.85 mmol) and piperidine (0.678 g, 6.85 mmol). The reaction mixture was heated at 95 C. for 72 hours. The cooled solution was diluted with saturated aqueous NaH2PO4 and extracted with ethyl acetate. The organic fraction was concentrated

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

Reference:
Patent; AbbVie Inc.; Reata Pharmaceuticals, Inc.; Donner, Pamela; Wagner, Rolf; Shanley, Jason; Heyman, Howard; Krueger, Allan; Chen, Hui-Ju; Rozema, Michael; Grampovnik, David; Visnick, Melean; Anderson, Eric; Jiang, Xin; Bender, Christopher F.; Bolton, Gary Louis; Caprathe, Bradley William; Lee, Chitase; Roark, William Howard; US2015/225397; (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. 723286-68-8, name is Ethyl 5,6,7,8-Tetrahydro-1,2,4-triazolo[4,3-a]pyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C8H12N4O2

Example 240 Preparation of 7-[(S)-4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid ethyl ester (240) A solution of Intermediates C (4.88 g, 20.0 mmol) and X (4.76 g, 24.3 mmol) in dry DCE (145 mL) is stirred for 20 min Sodium triacetoxyborohydride (8.58 g, 40.5 mmol) is added, and the reaction is stirred at rt overnight. The mixture is diluted with DCM and washed with sat. NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford the title product 240. (LC/MS method 16: ES+ m/z 422.3 [M+H]+, Rt=2.81 min)

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; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/236468; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, 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. category: Pyrazines

AIL round-bottomed flask was charged with 2-acetylpyrazine (25 g), glacial acetic acid (175 mL), and a 30 wt% solution of HBr in acetic acid (40 mL). Pyridinium tribronide (70 g) was added to the mixture all at once as a solid. The slurry was allowed to stir for 1 h at room temperature. This resulting solution was poured into diethyl ether (1.5 L) giving a yellow solid which was recovered by gravity filtration, washed with [CH3CN] (3 x 500 [RI)] and then diethyl ether (2 x 250 [ML)] to afford 34.9 g of the title compound. Physical characteristics. MS m/z 201,202.

The synthetic route of Acetylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; FLECK, Bruce, Francis; WO2004/22567; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-25-1, 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 33332-25-1 as follows.

EXAMPLE 43A. [00211] A solution of methyl 3-hydroxy-5-isopropoxybenzoate (Bioorg. Med. Chem. Lett., 15:2103 (2005)) (609 mg, 2.90 mmol), methyl 5-chloropyrazine-2- carboxylate (500 mg, 2.90 mmol), and K2CO3 (1.20 mg, 8.69 mmol) in CH3CN (20 mL) was heated to 8O0C for 2 h under an atmosphere of Ar (g). The reaction was cooled to RT, diluted with CH2Cl2 (50 mL) and filtered. The filtrate was concentrated in vacuo, and the residue was chromatographed (SiO2; 40 g; continuous gradient from 100% hexane to 100% EtOAc over 40 min) to provide Part A compound (1.005 g, 100% yield) as a colorless oil. [M + H]+ = 347.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/154563; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, 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 122-05-4, Product Details of 122-05-4

A ScCl3·6H2O (30 mg, 0.116 mmol) solution in distilled water (1.0 ml)was mixed with a H2pzc dihydrate solution (35 mg, 0.171 mmol) in N,N-dimethylformamide (1.0 ml). Acetonitrile (2.0 ml)and 0.25 ml of concentrated hydrochloric acid were added to the mixture. The prepared reaction mixture was placed intoa sealed glass tube and kept at 100 C for 24 h. The obtained colorless plate-like crystals were filtered off, washed by twoportions (2 ml) of acetonitrile and dried in air. The product yield was 40 mg (89%). Elemental analysis: found (%) C 37.1,H 3.4, N 14.2. Calculated for C24H24N8O16Sc2 (%): C 37.4, H 3.1, N 14.5. IR spectrum (KBr), v, cm-1: 392 (m), 427 (m),490 (m), 510 (s), 530 (s), 694 (m), 776 (s), 846 (s), 950 (w), 1051 (s), 1121 (m), 1179 (s), 1298 (s), 1386 (s), 1477 (s),1673 (s), 2510 (w), 2818 (w), 3104 (w), 3380 (w), 3491 (w).

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:
Article; Barsukova; Sapianik; Samsonenko; Fedin; Journal of Structural Chemistry; vol. 60; 5; (2019); p. 823 – 829; Zh. Strukt. Kim.; vol. 60; 5; (2019); p. 857 – 863,7;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem