Month: June 2021

These common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, 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. Formula: C6H2N2O3

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

The synthetic route of 2,3-Pyrazinecarboxylic anhydride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4430-75-5, These common heterocyclic compound, 4430-75-5, name is Octahydro-2H-pyrido[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.

HATU (38 mg, 0.10 mmol) was added to a stirring solution of acid (40 mg, 0.077 mmol) and octahydro-1H-pyrido[1,2-a]pyrazine (21 mg, 0.15 mmol) in DMF (0.5 mL) and TEA (0.06 mL, 0.4 mmol), and the reaction was stirred at rt for 3 h. The reaction mixture was diluted with MeOH (1 mL), filtered and purified by preparative HPLC (Xterra Prep MS C18 5u 30×100 mm, Eluent A: 5% acetonitrile/water with 10 mM ammonium acetate, Eluent B: 95% acetonitrile/water with 10 mM ammonium acetate, Flow Rate: 42 mL/min, linear gradient from 15% Eluent B to 100% Eluent B over 15 min) to yield 8-cyclohexyl-11-methoxy-N-(methylsulfonyl)-1a-(octahydro-2H-pyrido[1,2-a]pyrazin-2-ylcarbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide (36.2 mg, 0.056 mmol, 73% yield) as a white solid. The compound was isolated as a mixture of four stereoisomers. Presents as a 1:3 mixture of rotamers or atrope isomers and 1:1 mixture of diastereomers. Partial 1HNMR (300 MHz, CDCl3) delta 3.36 (s, 3H), 3.84 (s, 0.75H), 3.84 (s, 2.25H), 6.81-7.09 (m, 2H), 7.15-7.29 (m, 1H), 7.46-7.78 (m, 1.2H), 7.83 (d, J=8.4 Hz, 0.38H), 7.84 (d, J=8.4 Hz, 0.38H), 7.97 (br s, 0.75H), 8.01 (br s, 0.25H). LC-MS retention time: 2.22 min; m/z 643 (MH-). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Statistics shows that Octahydro-2H-pyrido[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 4430-75-5.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/226590; (2008); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H4BrN3O2

EDAC (2.79 g, 14.5 mmol) was added to a stirring, room temperature solution of IM19B (1.48 g, 7 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (1.27 g, 5.83 mmol), and hydroxybenzotriazole (0.39 g, 2.9 mmol) in DMSO (9 mL). After stirring for 1 day, 50 mL of water was added to the reaction mixture, to give a gooh. This residue was partitioned between EtOAc (2×100 mL) and additional water (50 mL). The combined organic phases were then extracted with saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 2.50 g (T.W. 2.40 g) of desired IM19C as a brown oil. TLC: 100% EtOAc Rf=0.55, with slight impurities at Rf=0.75 and Rf=0.9; LC/MS (dissolved in CH3CN/MeOH)>98% (M+H=412, with Br pattern, consistent with desired product, and also a M+23=434, also with Br pattern and also consistent with the desired product). Proceeded and used IM19C for subsequent reaction without further manipulation.

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; Atrin Pharmaceuticals LLC; Breslin, Henry Joseph; Gilad, Oren; (92 pag.)US2016/102104; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59303-10-5, These common heterocyclic compound, 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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.

General procedure: . Following GP2, t-BuOK (0.1 g, 1 eq., 0.88 mmol) was added to a solution of tert-butyl (1R,3r,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (0.2 g, 1 eq., 0.88 mmol), and 2-chloro-5-methylpyrazine (0.11 g, 1 eq., 0.88 mmol) in dry THF (7 mL). The reaction mixture was refluxed for 16 h. Then, the mixture was quenched with water (15 mL) and extracted with DCM (210 mL). The organic extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 25%). UPLC-MS (method A): Rt. 2.58 min (TIC); ionization ES+320 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 8.17 (d, J=1.3 Hz, 1H), 8.06 (s, 1H), 5.26 (t, J=5.0 Hz, 1H), 4.18-4.03 (m, 2H), 2.39 (s, 3H), 2.17-1.97 (m, 4H), 1.96-1.77 (m, 4H), 1.42 (s, 9H).

Statistics shows that 2-Chloro-5-methylpyrazine is playing an increasingly important role. we look forward to future research findings about 59303-10-5.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 109838-85-9

A 1.6M n-butyllithium solution in hexane (100 ml) is added dropwise [AT-75°] C. to a solution of (2R) -2, 5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (29.5 g) in absolute tetrahydrofuran (530 ml). The reaction mixture is then stirred [AT-75°] C. for 30 minutes, and then a solution of 2 [(S)- (BENZYLOXYMETHYL)-3-METHYL-BUTYL] bromide (29 g) in tetrahydrofuran (130 ml) is added over a period of 20 minutes. The reaction solution is stirred [AT-75°] C. for a further 2 hours and is then left to stand [AT-18°] C. for 64 hours. The reaction mixture is concentrated by evaporation, water (500 ml) is added, and extraction is carried out with diethyl ether [(3X500] ml). The organic phases are washed with saturated sodium chloride solution (500 ml), dried over magnesium sulfate and concentrated by evaporation. The evaporation residue is purified by FC (2.4 kg of silica gel, ethyl acetate-hexane 1: 15), and the title compound (36.2 g) is obtained in the form of a yellowish oil: Rf (B) =0.58. HPLC Rt =25.8 min.

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 109838-85-9.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/103652; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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. Recommanded Product: 54608-52-5

Step 2. (3S,4R)-4-methylbenzyl 3-fluoro-4-((2-(pyrazin-2-yl)-hydrazinecarboxamido)methyl)- piperidine-l-carboxylate [0205] A solution of (3S, 4 ?)-4-methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate (600 mg, 2.59 mmol) in dichloromethane (3 mL) was added to a solution of triphosgene (260 mg, 2.57 mmol) in dichloromethane (5 m L) at 0 C under nitrogen. Triethylamine (0.68 mL, 4.96 mmol) in dichloromethane (3 m L) was then added dropwise and the mixture was stirred at room temperature. After stirring for 2 hours, the mixture was cooled to 0 C and 2-hydrazinyl pyrazine (272 mg, 2.46 mmol) in dichloromethane (5 m L) was added. The reaction mixture was stirred overnight at room temperature. The mixture was diluted with dichloromethane, and washed with saturated NaHC03, brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (5% MeOH-DCM) to afford the title compound as a yellow powder (423 mg, 40 %). MS (ESI) calcd for C20H25FN6O3: 416.2; found: 417.2 [M+H]. *H NM (400 M Hz, CD3OD) delta 8.09 (d, J = 2.0 Hz, 2H), 7.94 (d, J = 2.0 Hz, 1H), 7.23 (d, J = 8.0 Hz, 2H), 7.16 (d, J = 8.0 Hz, 2H), 5.09-5.03 (m, 2H), 4.77-4.56 (m, 1H), 4.45-4.35 (m, 1H), 4.24-4.16 (m, 1H), 3.26-3.21 (m, 1H), 3.19-3.12 (m, 1H), 3.07-2.76 (m, 2H), 2.33 (s, 3H), 1.98-1.82 ( m, 1H ), 1.57-1.39 (m, 2H).

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

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 957344-74-0, 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.

Typical example of compound of formula (E).General procedure for amine displacement[00251] Amine (1.5eq , 10 8mmol) and (1.5eq, 10.8mmol) are added to a solution of 5,8-dibromo-imidazo[l,2-a]pyrazme (1.99g, 7.2mmol) m ethanol (6mL), and the reaction stirred at 800C for 15 hours. Ethanol is removed in vacuo and the product taken up m DCM and washed with water, dried over MgSO4 and concentrated in vacuo. The resultant oil is passed through a pad of silica using DCM and concentrated in vacuo to yield the desired product; Synthesis of Intermediates Intermediate 1: (5-Bromo-imidazo[l,2-a]pyrazin-8-yl)-(4-chloro-phenyl)-amine.[00254] Following the general procedure for amine displacement 5,8-dibromo-imidazo[l,2- ajpyrazme (1 99g, 7 2mmol) and 4-chloroamlme (1 37g, 10 8mmol) are coupled to give the title compound Purification on silica gel with dichloromethane, methanol (98 2) gives the final product [00255] HPLC (254nm) Rt 3 04mm (100%), m/z (APCI) 323, 325, 327 (M+H)+, 1H NMR(250MHz, CDCl3) delta(ppm) 7 32-7 36 (2H, m), 7 56 (IH, s), 7 64 (IH, m), 7 76-7 80 (3H, m), 7 96 (IH, br s)

Statistics shows that 5,8-Dibromoimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 957344-74-0.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 3-Amino-6-bromopyrazine-2-carboxylic acid

Example 8 : 3-[5-amino-6-(5-phenyl-l,3,4-oxadiazol-2-yl)pyrazin-2-yl]prop-2-yn-l-ol (Compound 11-90)SCHEME VIIICompound 11-90METHOD H:Step 1 : 3-Amino-6-bromo-iV-(phenylcarbonyl)pyrazine-2-carbohydrazide[00158] TBTU (22.09 g, 68.80 mmol) and triethylamine (4.642 g, 6.394 mL, 45.87 mmol) were added to a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol) and benzohydrazide (7.494 g, 55.04 mmol) in DMF (100.0 mL) and the resulting solution stirred at ambient temperature for 48 hours and then poured into water (400mL) with vigorous stirring. This was allowed to stir for 30 minutes, filtered and washed with water. The moist solid was dissolved in hot EtOAc, dried (MgSC^), filtered and concentrated in vacuo and the resultant solid dried under vacuum to give the desired product (11.34g, 73% Yield). ¾ NMR (400.0 MHz, DMSO) delta 7.51 (2H, m), 7.61 (1H, m), 7.69 (2H, br s), 7.92 (2H, m), 8.44 (1H, s), 10.48 (1H, br s), 10.54 (1H, br s) ppm; MS (ES+) 338.01.

The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 21948-70-9, name is 2-Methylthiopyrazine, 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. Recommanded Product: 21948-70-9

In this example, N-heterocycles such as thiomethylpyrazine and isoquinoline were reacted with iPr2NBEt3 · Met bases generating the organoborate intermediates which were subsequently reacted in Suzuki type cross-coupling reactions furnishing the corresponding substituted N-heterocycles 6h-j as shown in Scheme 8a and Table 4.Scheme 8aAs shown in Scheme 8a, the substrate is reacted with the base to form a metallic organoborate intermediate. The metallic organoborate intermediate is reacted with the electrophile identified in Table 4 to form the respective products by cross-coupling the metallic organoborate intermediate with the Ar-Br electrophile (0.8 equiv) and ZnCl2 (10 mol%) in the presence of Pd(OAc)2 (3 mol%) and S-Phos (6 mol%) at 50C for 12 hours. All reactions were conducted in THF. The results are shown in Table 4 below. Table 4: Functionalization of N-heterocycles using iPr2NBEt3-derived bases6j : 79

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

Reference:
Patent; HAAG, Benjamin; WO2012/85169; (2012); 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

3,5-Dichloropyrazine-2-carbonitrile (108.0 mg, 0.62 mmol) and 3-(4- cyclopropylphenyl)-1-oxa-3,7-diazaspiro[4.5]decan-2-one (162.5 mg, 0.597 mmol) were dissolved in DMF (1.5 mL), DIPEA (210.0 muL, 1.194 mmol) and the mixture was stirred at room temperature overnight under a nitrogen atmosphere. The mixture was poured into ice and extracted with ethyl acetate. The organic phase was separated, dried over Na2SO4 and concentrated. The residue purified by silica flash chromatography with 0 to 100% ethyl acetate in cyclohexane to give 3-chloro-5-[3-(4-cyclopropylphenyl)-2-oxo-1-oxa-3,7- diazaspiro[4.5]decan-7-yl]pyrazine-2-carbonitrile (161.5.2 mg, 66% yield). MS found for C21H20ClN5O2 as (M+H)+ 409.97.

According to the analysis of related databases, 313339-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem