Category: 136927-64-5

Adding a certain compound to certain chemical reactions, such as: 136927-64-5, name is 1-Chloropyrrolo[1,2-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 136927-64-5, Safety of 1-Chloropyrrolo[1,2-a]pyrazine

To a mixture of 1 (1.0 g, 4.6 mmol) and 580 mg of 2 (580 mg, 3.8 mmol) was added 1.7 ml of Hunig?s base (9.5mmol). The resulting mixture was stirred at 130 C. for 3 h. After the mixture was cooled down to room temperature, 200 ml of isopropanol/chloroform (1:2) was added, and the organics were washed with saturated aqueous NaHC03 (2×20 ml)and brine (2×50 ml). The organics were dried over MgS04 and concentrated under reduced pressure. The residue was purified via flash column chromatography on silica gel (0-10% MeOH in EtOAc) to get the desired product 3 as a brown powder (700 mg, 46%).

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; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 136927-64-5,Some common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, molecular formula is C7H5ClN2, 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 mixture of a (248 mg, 1.0 mmol) and b (152 mg, 1.0 mmol) was added 2.0 mL of Hunig?s base (9.5 mmol).The resulting mixture was stirred at 130 C. for 3 h. After the mixture was cooled down to room temperature, 100 mL of isopropanol/chloroform (1:2) was added, and the mixture was then washed with saturated aqueous NaHCO3 (2×20 mL) and brine (2×50 mL). The organics were dried over MgS04 and concentrated under reduced pressure. The residue was purified via flash chromatography on silica gel (0-10% MeOH inEtOAc) to get the desired product as a brown powder (250 mg, 67%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloropyrrolo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 136927-64-5, These common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[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.

To a solution of the product of Example 4A in dioxane (1mL) were added 1- chloropyrrolo[1,2-a]pyrazine (64.3 mg, 0.421 mmol), palladium(II) acetate (7.89 mg, 0.035 mmol), xantphos (20.3 mg, 0.035 mmol), and potassium carbonate (146 mg, 1.05 mmol). The reaction mixture was heated at 80 C for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified with flash column chromatography (SiO2, heptane:ethyl acetate 0~100%) followed by preparative HPLC [Waters XBridge C185 mum OBD column, 30 × 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (8 mg, 0.020 mmol, 6% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.92 (s, 1H), 7.88 (d, J = 5.7 Hz, 1H), 7.86 – 7.82 (m, 1H), 7.52 (d, J = 4.3 Hz, 1H), 7.47 (t, J = 8.8 Hz, 1H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 7.00 (d, J = 5.7 Hz, 1H), 6.87 – 6.81 (m, 2H), 4.51 (s, 2H), 2.57 (s, 6H); MS (ESI+) m/z 401 (M+H)+.

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 136927-64-5, name is 1-Chloropyrrolo[1,2-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 136927-64-5, Computed Properties of C7H5ClN2

4-Bromo-3-methylphenol (0.26 g, 1.4 mmol), 1-chloropyrrolo[1,2- a]pyrazine (0.16 g, 1.1 mmol), and cesium carbonate (0.69 g, 2.14 mmol) were combined in dimethyl sulfoxide (5 mL), and the reaction mixture was degassed withnitrogen for 5 minutes. After it had been heated to 120 00 for 3 hours, the reaction mixture was cooled to room temperature and allowed to stand for 12 hours, whereupon it was diluted with ethyl acetate, then filtered through diatomaceous earth. The filter pad was rinsed with ethyl acetate, and the combined filtrates were washed with 1:1 water I saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, andconcentrated in vacuo. Purification using silica gel chromatography afforded the product (344 mg) containing some impurities (-60% purity). This material was used without further purification. LCMS m/z 303.0 [M+H].

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; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 136927-64-5, These common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[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.

To a solution of the product of Example 4 A in dioxane (lmL) were added 1- chloropyrrolo[l,2-a]pyrazine (64.3 mg, 0.421 mmol), palladium(II) acetate (7.89 mg, 0.035 mmol), xantphos (20.3 mg, 0.035 mmol), and potassium carbonate (146 mg, 1.05 mmol). The reaction mixture was heated at 80 C for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified with flash column chromatography (Si(, heptane:ethyl acetate 0-100%) followed by preparative HPLC [Waters XBridge C18 5 mupiiota OBD column, 30 x 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (8 mg, 0.020 mmol, 6% yield). JH NMR (400 MHz, DMSO-<) delta ppm 8.92 (s, 1H), 7.88 (d, J = 5.7 Hz, 1H), 7.86 - 7.82 (m, 1H), 7.52 (d, J = 4.3 Hz, 1H), 7.47 (t, J = 8.8 Hz, 1H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 7.00 (d, J = 5.7 Hz, 1H), 6.87 - 6.81 (m, 2H), 4.51 (s, 2H), 2.57 (s, 6H); MS (ESI+) m/z 401 (M+H)+. Statistics shows that 1-Chloropyrrolo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 136927-64-5. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 136927-64-5

The mixture of 1-chloropyrrolo[1,2-a]pyrazine (200 mg, 1.31 mmol) and pivalohy-drazide (346.47 mg, 2.62 mmol) in MeCN (20 mL) was stirred at 80 C. for 24 h. The solvent was removed to give the crude product, the crude product was purified by FCC (petroleum ether/ethyl acetate=100:0 to 70:30).

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 136927-64-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); 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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5ClN2

Compound C21 (500 mg, 2.22 mmol), 1-chloropyrrolo[1,2-a]pyrazine (339 mg, 2.22 mmol), cesium carbonate (796 mg, 2.44 mmol), and palladium(ll) acetate (53 mg,0.22 mmol) were combined in 1,4-dioxane (15 mL), and the solution was degassed with nitrogen for 15 minutes. Di-tert-butyl[3,4, 5,6-tetramethyl-2?, 4?,6?-tri(propan-2-yl) bi phenyl2-yl]phosphane (214 mg, 0.444 mmol) was added to the reaction mixture, which wasthen degassed for an additional 2 minutes. The reaction mixture was heated to 100 00 in a microwave reactor for 6 hours, whereupon it was cooled to room temperature andfiltered through diatomaceous earth. The filter cake was washed with ethyl acetate, andthe combined filtrates were concentrated in vacuo. Silica gel chromatography (Gradient:20% to 80% ethyl acetate in heptane) was followed by three triturations with heptane;the resulting material was purified again using silica gel chromatography (Gradient:50% to 70% ethyl acetate in heptane) to provide the product as a pale yellow solid.Yield: 361 mg, 1.06 mmol, 48%; 13. In this case, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene was used in lieu ofdi-teit-butyl[3,4, 5, 6-tetramethyl-2?, 4? ,6?-tri(propan-2-yl)biphenyl-2-yl]phosphane.14. 4-Bromo-3-fluorophenol was protected as its tri(propan-2-yl)]silyl ether, which was converted to [3-fluoro-4-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2- yl)phenoxy][tri(propan-2-yl)]silane using the chemistry described for synthesis of C2 from Cl. Suzuki reaction with 5-bromo-6-methylpyrim idine-4-carbonitrile, followed bydesilylation using tetraethylammonium fluoride, afforded the requisite 5-(2-fluoro-4- hydroxyphenyl)-6-methylpyrimidine-4-carbonitrile.

According to the analysis of related databases, 136927-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 136927-64-5,Some common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, molecular formula is C7H5ClN2, 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.

Compound C21 (500 mg, 2.22 mmol), 1-chloropyrrolo[1,2-a]pyrazine (339 mg, 2.22 mmol), cesium carbonate (796 mg, 2.44 mmol), and palladium(ll) acetate (53 mg,0.22 mmol) were combined in 1,4-dioxane (15 mL), and the solution was degassed with nitrogen for 15 minutes. Di-tert-butyl[3,4, 5,6-tetramethyl-2?, 4?,6?-tri(propan-2-yl) bi phenyl2-yl]phosphane (214 mg, 0.444 mmol) was added to the reaction mixture, which wasthen degassed for an additional 2 minutes. The reaction mixture was heated to 100 00 in a microwave reactor for 6 hours, whereupon it was cooled to room temperature andfiltered through diatomaceous earth. The filter cake was washed with ethyl acetate, andthe combined filtrates were concentrated in vacuo. Silica gel chromatography (Gradient:20% to 80% ethyl acetate in heptane) was followed by three triturations with heptane;the resulting material was purified again using silica gel chromatography (Gradient:50% to 70% ethyl acetate in heptane) to provide the product as a pale yellow solid.Yield: 361 mg, 1.06 mmol, 48%. LCMS m/z 342.1 [M+H]. 1H NMR (400 MHz, ODd3) oe9.05 (5, 1H), 7.82 (d, J=2.5 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.68-7.66 (m, 1H), 7.50(dd, J=2.5, 1.4 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.09 (d, J=4.9 Hz, 1H), 7.01-6.98 (m,1H), 6.89 (dd, J=2.5, 4.1 Hz, 1H), 2.36 (5, 6H).

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, 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. Computed Properties of C7H5ClN2

Compound C28 (150 mg, 0.500 mmol), 1-chloropyrrolo[1,2-a]pyrazine (76 mg,0.50 mmol), cesium carbonate (488 mg, 1.50 mmol), palladium(ll) acetate (12 mg, 50pmol), and di-teit-butyl [3,4, 5,6-tetramethyl-2?,4? ,6?-tri(propan-2-yl) biphenyl-2- yl]phosphane (47 mg, 98 pmol) were combined in 1,4-dioxane (3 mL), and the reaction was degassed with nitrogen for 5 minutes. After the reaction mixture had been heated to 120 00 in a microwave for 3 hours, it was cooled to room temperature and filteredthrough diatomaceous earth; the filter cake was rinsed with ethyl acetate. The combined filtrates were concentrated in vacuo and the crude residue was purified via silica gel column chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to provide the desired product as a yellow oil. Yield: 159 mg, 0.38 mmol, 77%. LCMS m/z 417.2 [M+H]. 1H NMR (400 MHz, CDCI3) characteristic peaks oe 7.62 (dd, J=1.0, 4.7Hz, 1H), 7.46 (dd, J=1.4, 2.5 Hz, 1H), 7.40 (brs, 1H), 7.38 (brs, 1H), 7.21-7.14 (m, 2H),7.08 (d, J=4.9 Hz, 1H), 6.99-6.97 (m, 1H), 6.85 (dd, J=4.1, 2.7 Hz, 1H), 6.15 (dd, J=11.0, 2.1 Hz, 1H), 4.20-4.17 (m, 1H), 3.80 (dt, J=11.5, 2.5 Hz), 2.12 (5, 3H), 2.01 (5, 3H).

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 136927-64-5, 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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Compound C18 (135 mg, 0.630 mmol), 1-chloropyrrolo[1,2-a]pyrazine (120 mg,0.760 mmol), cesium carbonate (308 mg, 0.945 mmol), palladium(ll) acetate (28 mg,0.13 mmol), and di-teit-butyl[3,4, 5,6-tetramethyl-2? 4? 6-tn (propan-2-yl)biphenyl-2- yl]phosphane (120 mg, 0.250 mmol) were combined in 1,4-dioxane (5 mL), and the reaction mixture was heated to 120 00. After 3 hours, it was cooled to room temperature and subjected to silica gel chromatography (Eluent: 4% methanol in ethylacetate) to provide the racemic product, which was subsequently separated into its component atropenantiomers via supercritical fluid chromatography (Column: Chiralpak AD-H, 5 pm; Eluent: 3:7 methanol I carbon dioxide). The first-eluting atropenantiomer was designated as 12, and exhibited a negative (-) rotation. Yield: 34.9 mg, 0.110 mmol, 17%. LCMS m/z331.1 [M+H]. 1H NMR (400 MHz, CDCI3)o 9.01 (brs, 1H), 7.62(dd, J=4.9, 0.8 Hz, 1H), 7.47 (dd, J=2.4, 1.4 Hz, 1H), 7.30 (d, J=2.2 Hz, 1H), 7.27-7.24 (m, 1H), 7.09 (d, J=4.9 Hz, 1H), 7.05 (d, J=6.3 Hz, 1H), 6.99-6.97 (m, 1H), 6.86 (dd, J=4.1, 2.7 Hz, 1H), 2.46 (5, 3H), 2.11 (5, 3H), 2.02 (5, 3H). The second-eluting atropenantiomer was designated as 13, and was found to have a positive (+) rotation. Yield: 30mg, 88 pmol, 14%. LCMS m/z331.1 [M+H]. 1H NMR (400 MHz, CDCI3) oe9.02 (brs, 1H), 7.63 (dd, J=4.7, 0.8 Hz, 1H), 7.46 (dd, J=2.5, 1.4 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H), 7.27-7.25 (m, 1H), 7.10 (d, J=4.9 Hz, 1H), 7.05 (d, J=8.2 Hz, 1H), 6.89 (dt, J=4.1, 1.2 Hz, 1H), 6.86 (dd, J=4.1, 3.5 Hz, 1H), 2.47 (5, 3H), 2.11 (5, 3H), 2.01 (5, 3H).

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

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem