Tag: M.W=200-300

Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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 C6H5Cl2N3O2

Example 3A – Synthesis of Synthesis of 3-amino-6-[4-(dimethylamino)phenyl]-5-{4- (methylsulfony.)phenyl]pyrazine-2-carboxylic acid; [00171] Step 1 : A mixture of methyl 3-amino-5, 6-dichloro-2-pyrazi?ecarboxylate (1.0 mmol, 222.0 mg), 4-(methyisulfo?yl) phenyl boronic acid (1.2 mmol, 240.0 mg), and tetrakis (triphenylphosphine) Pd (0) (0.12 mmol, 138.7 mg) in 50 ml of anhydrous dimethylformamide was mixed via inert conditions. A solution of potassium carbonate (5 mmoles, 691.1 mg) in deionized water (3 ml) was added to the reaction mixture and heated at 75 0C overnight under an argon atmosphere. The product was purified by reversed phase HPLC (5-75 acetonitrile with 0.1% trifluoroacetic acid at 50 mi/min on XBridge Prep C18 OBD 5um 30 x 150 mm. Retention time 5.9 min) and characterized by 1H and 13C NMR. 1 H NMR (500 MHz, DMSO-d6) delta 8.08 (dt apparent, J = 9.0 Hz1 2.0 Hz, 2H)1 delta 7.99 (dt apparent, J = 8.5 Hz1 1.5 Hz, 2H), delta 7.66 (bs, 2H), delta 3.30 (s, 3H). 13C NMR (125 MHz, DMSO-d6) delta 43.8 (s), delta 122.5 (s), delta 127.2 (s), delta 130.7 (s), delta 130.9 (s), delta 141.1 (s), delta 142.1 (s), delta 153.3 (s), delta 154.9 (S), delta 167.2 (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1458-18-0, its application will become more common.

Reference:
Patent; MALLINCKRODT INC.; NEUMANN, William, L.; FRESKOS, John, N.; DORSHOW, Richard, B.; WO2010/121003; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 848841-62-3, A common heterocyclic compound, 848841-62-3, name is 4-(6-Bromopyrazin-2-yl)morpholine, molecular formula is C8H10BrN3O, 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.

19b) 1-CHLORO-4- (6-MORPHOLIN-4-VL-PVRAZIN-2-YL)-ISOQUINOLINE A solution of 4-BROMO-1-CHLORO-ISOQUINOLINE (400 mg, 1.65 MMOL) in THF (20 mL) is cooled TO-72¡ãC. A solution of n-BuLi (2.5 M in hexanes) (0.80 mL, 2 MMOL) is added dropwise and the reaction temperature maintained AT-70 ¡ãC~-68¡ãC FOR 30min. ZnBr2 (408 mg, 1.91 MMOL) is dissolved in THF (6 mL) and is transferred to above mixture slowly at-70 ¡ãC. The solution is stirred 40 min at-70 ¡ãC, then warmed to room temperature by removing the cooling bath. Pd (PPh3) 4 (190 mg, 0.164 MMOL) in 6ML THF and 4-(6-BROMO-PYRAZIN-2-YL)- morpholine (400 mg, 1.65 MMOL) in THF (4 mL) are added to the reaction mixture dropwise, then the solution is heated to 60 ¡ãC for 30 min and then kept at rt overnight. The reaction mixture is diluted with ethyl acetate, washed with sat. NH4CI . then brine, and dried over sodium sulfate. The solution is concentrated until white solid came out from solution. The solid is collected by filtration, washed with ether and dried under vacuum. 300 mg of 1- CHLORO-4- (6-MORPHOLIN-4-YL-PYRAZIN-2-YL)-ISOQUINOLINE IS obtained. Yield was 56percent. MS/ESI+, M+1 = 327

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate, 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 C7H7BrN2O2

[0116j To a solution of methyl 5-(bromomethyl)pyrazine-2-carboxylate (0.15 g, 0.65 mmol) in chloroform (10 mL) was added hexamethylene tetramine (0.093 g, 0.66 mmol) and the reaction mixture was stirred at room temperature for 18 h. The solid formed was filtered and dried. The solid was suspended in methanol (10 mL), concentrated hydrochloric acid (0.3 ml) was added and the reaction mixture was heated at 75 C for 3 h. The reaction mixture was concentrated, the residue was triturated with diethyl ether and dried to afford the title compound methyl 5-(aminomethyl)pyrazine-2-carboxylate hydrochloride (0.15 g, crude) as a brownish solid. Calculated M+H: 168.07; Found M+H: 168.1.

The synthetic route of Methyl 5-(bromomethyl)pyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 221136-66-9, 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

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, Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, name: 2-Amino-3,5-dibromopyrazine

Intermediate Example 1 -2: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2- yl)methanolStep A: Preparation of ethyl 6,8-dibromoimidazo[1 , 2-a]pyrazi’ne-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10 C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 %) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCI3): delta =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.

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-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 mixture of methyl 3,5-dichloropyrazine-2-carboxylate (2.0 g, 9.7 mmol, synthesized via Step a of Intermediate A), trimethyl-l,3,5,2,4,6-trioxatriborinane (2.4 g, 19.3 mmol), Pd(PPh3)4 (558 mg, 483 pmol) and Cs2C03 (6.3 g, 19.3 mmol) in dioxane (70 mL) was stirred at 110 C for 12 hours under N2 atmosphere. The reaction mixture was concentrated in vacuo to give a residue, which was purified by silica gel chromatography (ethyl acetate in petroleum ether = 0% to 50% ) to afford methyl 3-chloro-5-methylpyrazine- 2-carboxylate (250 mg, 14% yield) as a yellow solid. LCMS m/z [M+H]+ = 187.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, 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 486424-37-7 as follows.

Treat a solution of 3-amino-6-bromo-pyrazine-2-carboxylic acid (214 g, 983 mmol) in dimethylformamide (1.07 L) with methylamine hydrochloride (79.7 g, 1.18 mol) and N,N-diisopropylethylamine (445 g, 3.44 mol) at 23 C. To the resulting suspension, add l-[bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (449 g, 1.18 mol) over 30 min. After 30 min, add H20 (4.29 L) over 2 h. Stir at 23 C for 30 min and then 1 h at 10 C. Filter, wash the solid with H20 (2 x 428 mL), and dry to give the title compound (227 g, 82 %). ES/MS m/z (79Br) 231.0 (M+H).

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-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. Safety of 6,8-Dibromoimidazo[1,2-a]pyrazine

To a solution of 6,8-dibromoimidazo[l,2-a]pyrazine (0.50 g, 1.8 mmol) [Combi- Blocks, OR-7964] in DMF (12 mL) was added N-iodosuccinimide (0.45 g, 2.0 mmol). The reaction mixture was then heated at 60 C for 15.5 h. The reaction mixture was concentrated in vacuo. The resulting solid was taken up into dichloromethane (DCM). The organic layer was washed sequentially with water and sat. Na2S203 (aq). The organic layer was then dried over Na2S04, filtered, and concentrated to afford the title compound as a light yellow solid (0.64 g, 88%). LCMS for CeltBrzINs (M+H)+: calculated m/z = 401.8, 403.8, 405.8; found 401.8, 403.7, 405.6.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; DOUTY, Brent; BUESKING, Andrew W.; BURNS, David M.; COMBS, Andrew P.; FALAHATPISHEH, Nikoo; JALLURI, Ravi Kumar; LEVY, Daniel; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; SHVARTSBART, Artem; SPARKS, Richard B.; YUE, Eddy W.; (355 pag.)WO2019/79469; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

Hydrazine hydrate (24 mL, 0.48 mol) was added dropwise to a stirred mixture of methyl 3-amino-6-bromopyrazine-2-carboxylate 29 (100 g, 0.42 mol) in EtOH (2 L). The mixture was heated at 50 C under nitrogen. The resulting thick suspension was stirred at 50 C for 16 h. Further hydrazine hydrate (2.5 mL) was added in one portion and the suspension was stirred at 50 C for a further 24 h. EtOH (500 mL) was charged to the thick reaction mixture and the mixture was allowed to cool to room temperature. The resulting suspension was filtered and the solid washed with ethanol (1 L) and dried in vacuo to give 3-amino-6-bromopyrazine-2-carbohydrazide (98 g, quantitative) as a cream solid. Pivalic anhydride (165 mL, 815 mmol) was added to a stirred mixture of 3-amino-6-bromopyrazine-2-carbohydrazide (172 g, 741 mmol) in acetonitrile (1.8 L) and the mixture was heated at 80 C for 1 h. The reaction was left to stir for 16 h. The required yellow solid material was isolated by filtration. The filtrate was partitioned between EtOAc (2 L) and aqueous sodium bicarbonate (2 L). The organic layer was washed with saturated brine and dried over MgSO4. The solution was filtered and concentrated to give an orange sticky solid which was triturated with MTBE (250 mL). The insoluble yellow solid was isolated by filtration. The combined solids were dried in vacuum at 50 C for 3 days to afford 3-amino-6-bromo-N’-pivaloylpyrazine-2-carbohydrazide (224 g, 96%) as a yellow solid. p-Toluenesulfonyl chloride (164 g, 862 mmol) was added portionwise to a suspension of 3-amino-6-bromo-N’-pivaloylpyrazine-2-carbohydrazide (227 g, 718 mmol) and DIPEA (300 mL, 1.8 mol) in acetonitrile (2.2 L). The mixture was stirred for 2 h at 70 C. The reaction was left to cool to room temperature overnight. The reaction mixture was partitioned between ethylacetate (2 L) and aq. sodium bicarbonate (2 L). The organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting brown/beige solid was triturated with hot MTBE (1 L), isolated by filtration and dried to afford 5-bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 30 as a yellow solid (187 g, 87%). The mother liquors were evaporated to dryness. The crude solid was triturated with MTBE (500 mL), filtered and washed with 100 mL of MTBE. The resulting solid was air dried overnight to afford a second crop of 5-bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 30 (36 g, 17%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Article; Barlaam, Bernard; Cosulich, Sabina; Delouvrie, Benedicte; Ellston, Rebecca; Fitzek, Martina; Germain, Herve; Green, Stephen; Hancox, Urs; Harris, Craig S.; Hudson, Kevin; Lambert-Van Der Brempt, Christine; Lebraud, Honorine; Magnien, Francoise; Lamorlette, Maryannick; Le Griffon, Antoine; Morgentin, Remy; Ouvry, Gilles; Page, Ken; Pasquet, Georges; Polanska, Urszula; Ruston, Linette; Saleh, Twana; Vautier, Michel; Ward, Lara; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5155 – 5162;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 957344-74-0, name is 5,8-Dibromoimidazo[1,2-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. HPLC of Formula: C6H3Br2N3

Step 3 4-(5-Bromo-iotamiotadazo[l 2-a]pyraziotan-8-ylamiotano)-2-methoxy-N-(6-methylpyriotadiotan-3-ylmethyl) benzamide[00367] 5,8-dibromoimidazo[l,2-a]pyrazme (285 mg, 1 03 mmol) and 4-ammo-2-methoxy-/V-[(6-methylpy?dm-3-yl)methyl]benzamide (280 mg, 1 03 mmol) are stirred in 1PrOH (5 mL) and HBr (48% aq , 380 muL) is added The mixture is heated at reflux for 24 hours The cooled suspension is poured into NaHCO3 (sat aq , 25 mL) and water (25 mL) and extracted with CHCI3 (3 x 40 mL) The extracts are dried over MgStheta4 and evaporated The residue is purified by column chromatography, elutmg with 10% – 20% DCM/MeOH to afford the title compound as a pale yellow solid (200 mg, 0 43 mmol)

The synthetic route of 5,8-Dibromoimidazo[1,2-a]pyrazine 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