Month: April 2022

Electric Literature of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Article; Coombs, Thomas C.; Tanega, Cordelle; Shen, Min; Wang, Jenna L.; Auld, Douglas S.; Gerritz, Samuel W.; Schoenen, Frank J.; Thomas, Craig J.; Aube, Jeffrey; Bioorganic and Medicinal Chemistry Letters; vol. 23; 12; (2013); p. 3654 – 3661;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1057682-05-9, name is (R)-6-(3-Methylpiperazin-1-yl)nicotinonitrile, molecular formula is C11H14N4, The 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. HPLC of Formula: C11H14N4

To a stirred solution of 3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoic acid (5.0 g, 21.19mmol, obtained from Example 29, step 3) in dry DMF (40 mL, -8 vol), 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile ( 4.06 g, 20 mmol), EDClHCl (6.08 g, 31.6 mmol),HOBt (3.43 g, 25.4 mmol) and DIPEA (14.5 mL, 84.5 mol) were added at 10-15C andstirred for 22 h. The reaction mixture was quenched with ice cold water (500 mL) andextracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrousNa2S04 and concentrated under reduced pressure to get crude compound. Crude compoundwas stirred with EtOAc (50 mL) for 1 hour at RT, filtered and suck dried. Solid obtained wasagain made slurry with EtOAc. Filtered the solid and washed with EtOAc (50 mL) to afford(50 mL) 6-[(3R)-4-[3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoyl]-3-methyl-piperazin-1-yl]pyridine-3-carbonitrile in 43% yield (3.8g). Chiral HPLC was used to confirm that thecompound is the enantiomer of compound 29. Column used: Lux,5 micron, Cellulose-4 (250X 4.6 mm , 5 micron , Mobile phase: 50:50 n-hexane:(0.1% HCOOH in 1:1ethanol:methanol), Flow rate: 1.0 mL/min, Temperature: 25C. Retention time for Renantiomer= 12.9 min; Retention time for compound 29 = 13.4 min.

With the rapid development of chemical substances, we look forward to future research findings about 1057682-05-9.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17322-91-7, 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. 17322-91-7, name is 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one. A new synthetic method of this compound is introduced below.

Dissolve 5-hydroxy-1H-pyrrole[3,2]pyridine (10 mmol) in 40 ml of dichloromethane and add 10 ml to it.Triethylamine, controlled temperature below 10 C, adding 2-chloroacetyl chloride (12 mmol) in dichloromethane to the system, adding dropwiseAfter completion, return to room temperature, stir at room temperature for 10 hours, then wash the reaction system with 50 ml of 5% aqueous sodium carbonate solution, organic phase.After drying with anhydrous Na 2 SO 4 and evaporating the solvent, the obtained solid was separated by flash column chromatography.1.9 g pale yellow 2-chloro-1-(5-Hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid, yield 90%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17322-91-7, its application will become more common.

Reference:
Patent; Sang Qi; (10 pag.)CN108383838; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-61-8, 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 1122-61-8 as follows.

Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-61-8, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5648496; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, The 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. name: 2-(Bromoacetyl)pyridine hydrobromide

[0284] 7V-(3-Methylphenyl)-4-(2-pyridinyl)-l,3-thiazol-2-amine (68). A mixture of bromoketone hydrobromide 67 (0.96 g, 3.4 mmol) and 3- methylphenylthiourea (4) (0.57 g, 3.4 mmol) in EtOH (25 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 0C, diluted with water (40 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 68 (0.74 g, 81%) as a cream powder: mp (EtOAc) 164-166 0C; 1H NMR delta 10.20 (br s, 1 H, NH), 8.58 (ddd, J= 4.7, 1.7, 0.8 Hz, 1 H, H-6′), 7.99 (dt, J= 7.9, 0.9 Hz, 1 H, H-3′), 7.99 (ddd, J= 7.9, 7.5, 1.8 Hz, 1 H, H-4′), 7.58 (br d, J= 8.1 Hz, 1 H, H- 6′), 7.52 (s, 1 H, H-5), 7.47 (br s, 1 H, H-2″), 7.31 (ddd, J= 7.5, 4.7, 1.2 Hz, 1 H, H-5′), 7.24 (t, J= 7.8 Hz, 1 H, H-5″), 6.80 (br d, J= 7.5 Hz, 1 H, H-4″), 2.33 (s, 3 H5 CH3); 13C NMR delta 163.3, 152.0, 150.2, 149.3, 141.0, 138.0, 137.1, 128.8, 122.4, 122.0, 120.2, 117.4, 114.0, 106.5, 21.2; MS m/z 268.4 (MH+, 100%). Anal, calcd for Ci5Hi3N3: C, 67.39; H, 4.90; N, 15.72. Found: C, 67.13; H, 5.10; N, 15.67%.

With the rapid development of chemical substances, we look forward to future research findings about 17570-98-8.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13296-04-3, 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 13296-04-3 as follows.

B. Preparation of N-[4-(pyridin-4-yl)phenyl]-2-(2-fluorophenyl)-2-(4- chlorophenylaminocarbonylamino)-acetamide; [0367] To a solution of 2-fluororhohenylglycine (0.157 g, 0.930 mmol) in DMF (4 mL), 4- chlorophenylisocyanate (0.143 g, 0.930 mmol) was added. The mixture was stirred at room temperature overnight. To the solution, 4-(pyridin-4-yl)phenylamine (0.150 g, 0.880 mmol) was added, followed by addition of EDC (0.339 g, 1.77 mmol). The mixture was then stirred EPO at room temperature overnight. It was concentrated in vacuo. The residue was dissolved in CH3CN. H2O was then added to induce precipitation. The precipitates were collected by filtration (0.215 g). MS 475.1 and 477.1 (M+H, Cl pattern).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13296-04-3, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2006/63113; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58553-48-3, 5-(Hydroxymethyl)picolinonitrile, 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, 58553-48-3, blongs to pyridine-derivatives compound. Quality Control of 5-(Hydroxymethyl)picolinonitrile

5- (Hydroxymethyl) pyridine-2-carbonitrile (4 g, 0.03 mol; see step (ii) above) was dissolved in 25 mL of methylene chloride and cooled in an ice bath. [MESYL] chloride (2.32 mL, 0.0300 mol) and then triethylamine (4.6 mL, 0.033 mol) were added dropwise. The reaction mixture was stirred and after work up the crude mesylate was treated with NaN3 (7.35 g, 0. [113 MOL)] in 20 mL of DMF. The reaction mixture was stirred at [40C] for 2 h, diluted with water and extracted with ethyl acetate. The organic layer was concentrated to yield 3.95g (83%) of the crude azide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58553-48-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2003/101956; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride, the common compound, a new synthetic route is introduced below. Computed Properties of C8H11ClN2O2

Intermediate 8: methyl 6-(f r(4-chlorophenyl)sulfonyllaminolmethyl)nicotinate A cooled (0 0C) solution of methyl-6-aminomethyl pyridine-3-carboxylate.HCI (700 mg; 3.45 mmol) and triethylamine (0.96 ml; 6.91 mmol) in DCM (14 ml) was treated with a solution of4-chlorobenzenesulfonyl chloride (729 mg; 3.45 mmol) in DCM (10 mL). After stirring for 20 h, the mixture was diluted with DCM and washed with water and sat. NaHCO3 solution. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated to give solid, which was crystallised from DCM/Cyclohexane to afford the title compound as a grey solid (524mg, 45 %).1 H NMR (DMSO-c/6, 300MHz): 8 8.91 (1 H, d, J = 1 .5 Hz), 8.54 (1 H, t, J = 6.5 Hz), 8.23 (1 H, dd, J = 8.0 Hz, J = 2.0 Hz), 7.76 (2H, d, J = 8.5 Hz), 7.62 (2H, d, J = 8.5 Hz), 7.50 (1 H, d, J =8.0 Hz) 4.21 (2H, d, J = 6.5 Hz), 3.88 (3H, s). MS (ESI+): 341.1 . HPLC (Condition A): Rt 3.37 min (HPLC purity 97.7%).

The synthetic route of 1072438-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/124962; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 868551-30-8, Methyl 4-methyl-5-nitropicolinate, 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, HPLC of Formula: C8H8N2O4, blongs to pyridine-derivatives compound. HPLC of Formula: C8H8N2O4

To a solution of methyl 4-methyl-5-nitropicolinate (810 mg, 4.1 mmol) in ethanol (150 ml) was added palladium on carbon (10 wt.%, 85 mg, 4.1 mmol) at room temperature. Hydrogenation was carried out in a parr shaker at 45 psi for 3 h. Additional palladium on carbon was added (170 mg) and the reaction was continued at 39 psi for 23 h. The mixture was filtered through CELITE and concentrated to provide methyl 5-amino-4-methylpicolinate, which was directly used in the next step without further purification. LC-MS (IE, m/z): 167 [M + 1]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,868551-30-8, Methyl 4-methyl-5-nitropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CATO, Brian; FRIE, Jessica, L.; KIM, Dooseop; PASTERNAK, Alexander; SHI, Zhi-Cai; WO2014/85210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 71670-70-7 ,Some common heterocyclic compound, 71670-70-7, molecular formula is C7H9Cl2N, 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.

A mixture of 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 17), (270 mg), 2-(chloromethyl)-5-methylpyridine hydrochloride (180 mg) and cesium carbonate (689 mg) in DMF (3 mL) was stirred at rt overnight. The crude product was purified by prep. LCMS then azeotroped with DCM to remove the residual AcOH to give the desired compound (141 mg). LCMS: m/z 399.20 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.04-1.67 (m, 4H) 1.79 (d, J=9.2 Hz, 2H) 1.97-2.21 (m, 2H) 2.32 (s, 3H) 3.56 (td, J=9.9, 4.5 Hz, 1H) 3.79-4.00 (m, 1H) 5.61-5.98 (m, 2H) 6.69 (d, J=8.0 Hz, 1H) 7.17 (d, J=5.1 Hz, 1H) 7.41 (d, J=7.7 Hz, 1H) 8.14 (s, 1H) 8.35 (d, J=5.1 Hz, 1H) 8.41 (s, 1H) 9.04 (d, J=6.5 Hz, 1H)

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. 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem