Month: July 2021

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

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

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

132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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. Recommanded Product: 2-Bromo-1-(pyrazin-2-yl)ethanone

To a solution of 1-(pyridin-2-yl)thiourea (0.129 g, 0.85 mmol) in DMF (7 mL), 2-bromo-1-(pyrazin-2-yl)ethan-1-one (0.20 g,0.99 mmol) and triethylamine (0.3 mL, 2.0 mmol) were added successively and heated the mixtureat 70C for 2 hours. After TLC showed completion, reaction mixture was diluted withEtOAc (20 mL) and washed with water (3 x 10 mL). The organic layer was dried over Na2SO4and concentrated. The resulting residue was purified by column chromatography (silicagel,100-200) and the desired product was eluted with 3% CH3OH in CH2Cl2. Concentration ofthe pure fractions afforded 58 (35 mg, 13.8% yield), as a greenish solid; 1H NMR: (400 MHz,DMSO-d6): delta 6.95 (d, J = 4.8 Hz, 1H), 7.11 (d, J = 8.4 Hz, 1H), 7.71-7.76 (m, 1H), 7.79 (s, 1H),8.32-8.33 (m, 1H), 8.58 (d, J = 2.4 Hz, 1H), 8.65-8.66 (m, 1H), 9.16 (d, J = 1.6 Hz, 1H), 11.57(s, 1H); 13C NMR: (300 MHz, DMSO-d6): 111.3, 114.5, 116.8, 117.0, 138.6, 146.8, 147.2, 152.0,158.8, 158.9, 159.0, 160.7; LCMS m/z (M+H) 256.04, purity 98.9%; HRMSMS ESI m/z calcdfor C12H9N5S (M+H)+ 256.06122, found 256.0634 (Delta 2.2 ppm).

The synthetic route of 132426-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kesicki, Edward A.; Bailey, Mai A.; Ovechkina, Yulia; Early, Julie V.; Alling, Torey; Bowman, Julie; Zuniga, Edison S.; Dalai, Suryakanta; Kumar, Naresh; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua O.; Parish, Tanya; PLoS ONE; vol. 11; 5; (2016);,
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

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

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

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, 767340-03-4, name is (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine, 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

Ligand Metal precursor percentyieldb percent eec config. 15 3 A [Rh(cod) 2]BF4 77 88 R 4 B [Rh(cod)Cl]2 58 76 R 5 C [Rh(cod)Cl]2 15 78 a: Reaction conditions: in TFE, 5 molpercent metal precursor, 5 molpercent ligand, 90 psig H2, 50 °C, 18 h; b: Assayed by HPLC; c: Assayed by chiral HPLC using a AS-RH chiral column eluting with 20percent acetonitrile/water as the mobile phase.

The synthetic route of (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; SOLVIAS AG; WO2005/97733; (2005); 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C16H11ClN2

To a solution of 1.00 g of 2-chloro-5,6-diphenylpyrazine in 10 ml of methanol, 2.14 g of allylamine was added and the mixture was reacted in a sealed tube at 80C for 41 hours, followed by stirring at room temperature for 54 hours.. After the solvent was evaporated under reduced pressure, the reaction solution was combined with water, extracted with chloroform, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by silica gel column chromatography to obtain 330 mg of the desired compound as a pale yellow crystal having a melting point of 97 to 100C

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 41270-66-0.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1400518; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem