Tag: M.W:100-200

Electric Literature of 1092286-30-0, 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 1092286-30-0 as follows.

A mixture of 4-(6-(4-amino-4-methylpiperidin-l-yl)pyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile dihydrochloride (Intermediate P48;53 mg, 0.107 mmol), HATU (44.9mg, 0.118 mmol), and 5-Chloro-2-methyl-3- pyridinecarboxylic acid (36.9 mg, 0.107 mmol) in DMSO (1.28 mL, 0.1 M) was treated with DIEA (0.09 mL, 0.54 mmol) and then stirred for 18 h at ambient temperature. The reaction mixture was diluted with EtOAc and washed with water. The organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo. The residue was suspended in 60:40 ACN:water containing 2% TFA. The solution was purified directly by C18 reverse phase chromatography (5-95% ACN in water with 0.1% TFA as the gradient eluent) to afford the title compound as the TFA salt. The TFA salt was treated with saturated NaHCCb(aq) and extracted with DCM. The combined organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo to afford the title compound (26.1 mg, 42% yield). MS (apci) m/z = 574.2 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1092286-30-0, its application will become more common.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 197376-47-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl (6-chloropyridin-3-yl)acetate (8.2 g) in N,N-dimethylformamide (50 mL) was added sodium hydride (60% in mineral oil, 2.4 g) under ice-cooling, and the mixture was stirred for 30 min. To the reaction mixture was added methyl iodide (7.7 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added methyl iodide (3.8 mL), and the mixture was stirred at 40 C. for 15 hr. The reaction mixture was cooled to 0 C., N,N-dimethylformamide (15 mL) and sodium hydride (60% in mineral oil, 1.2 g) were added thereto, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added methyl iodide (2.5 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (4.4 g). (1557) MS(ESI+): [M+H]+ 227.8

According to the analysis of related databases, 197376-47-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866807-27-4, Adding some certain compound to certain chemical reactions, such as: 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid,molecular formula is C6H5ClN2O2, 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 866807-27-4.

Step 4: Preperation of 3-amino-6-chloro-pyridine-2- carboxylic acid methyl ester; 3-Amino-6-chloro-pyridine-2-carboxylic acid (636 mg) was suspended in methanol (8 mL) and toluene (22 mL) was added. A solution of (trimethylsilyl) diazomethane (2.0 M in hexane,2.4 mL) was added slowly to the reaction mixture. After 1 hour stirring at room temperature, another portion of(trimethylsilyl) diazomethane (550 mul) was added and the mixture was stirred for additional 45 minutes. The reaction mixture was quenched with water and extracted 3x with ethyl acetate. The combined organic layer was washed with 2N hydrochloric acid, saturated bicarbonate solution and brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, choroform/ethyl acetate = 50:1, Rf = 0.30) to afford 365 mg of the title compound of the formulaas a yellow solid. The compound still contained -30% of an unknown impurity and was used in the next step without further purification.1H-NMR (CDCl3, TMS) delta (ppm) : 3.96 (3H, s) , 5.82 (2H, br s), 7.05 (IH, d, J = 9 Hz), 7.23 (IH, d, J = 9 Hz).

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. 866807-27-4, 3-Amino-6-chloropyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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.

A 100 mL round-bottom flask was charged with NiCl2*6H2O (40 mg, 0.15 mmol) and DMF (10 mL). The resulting solution was stirred and heated to 40 C. Then, 2-chloro-5-methoxypyridine (6,3 mmol), anhydrous LiCl (130 mg, 3 mmol), and zinc dust (230 mg,3.6 mmol) were added. When the temperature rose to 50 C, a grain of iodine crystal and two drops of acetic acid were added to the mixture. The mixture was stirred at 55-60 C until complete conversion of 2-halopyridine (monitored by TLC). To the cooled reaction mixture was added 1 N HCl aqueous solution (5 mL) to consume the remaining zinc dust. The resulting mixture was made alkaline with aqueous ammonia (25%) and diluted with CH2Cl2. The organic layers were collected, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel (Hexane/EtOAc 10:1, v/v) to afford desired 5,5′-dimethoxy-2,2′-bipyridine as a light yellow solid, 130 mg, 40% yield. 1H NMR (500 MHz, CDCl3): d 8.33 (d, J 3.0 Hz, 2H, ArH), 8.24 (d, J 9.0 Hz,2H, ArH), 7.30 (dd, J1 9.0 Hz and J2 3.0 Hz, 2H, ArH), 3.91 (s, 6H,2OCH3).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Article; Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; 29; (2017); p. 4150 – 4159;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190320-33-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5FN2, molecular weight is 136.13, as common compound, the synthetic route is as follows.

Step 1: 6-Fluoro-lH-pyrrolo[3,2-b]pyridine N-oxide (60) 60 [00667] To a stirred solution of compound 24 (1.2 g, 8.8 mol, 1.0 eq.) in DCM (100 mL), was added mCPBA (2.3 g, 13.2 mmol, 1.5 eq.) at room temperature. After stirring at room temperature overnight, the reaction was cooled at 0 C for lh, and then filtered to collect the solid. The solid was washed with diethyl ether, and then dried under high vacuum give compound 60 (1.3 g, 8.5 mmol, 97%) as a solid, which is used without further purification.

Statistics shows that 1190320-33-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoro-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; AKARNA THERAPEUTICS, LTD.; MOHAN, Raju; PRATT, Benjamin, Anthony; (297 pag.)WO2016/103037; (2016); 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. 195140-86-4, name is 6-Isopropoxynicotinonitrile, the common compound, a new synthetic route is introduced below. Formula: C9H10N2O

Example 93 2-[6-Isopropoxy-3-pyridyl]-4H-1,3-benzothiazine-4-one A mixture of methyl thiosalicylate (1.85 g, 11.0 mmol), 2-isopropoxy-5-cyanopyridine (1.62 g, 10.0 mmol), triethylamine (1.80 ml, 12.9 mmol) and toluene (10 ml) was refluxed under nitrogen atmosphere for 30 hrs.. The reaction mixture was concentrated.. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) and recrystallized from ethyl acetate-isopropylether to give the titled compound (0.89 g, 30 %). mp. 109.7-110.4 C IR (KBr): 1663, 1595, 1570, 1522, 1487, 1381, 1285, 1238, 1096, 1063, 1030, 947, 922, 837, 745 cm-1.1H-NMR (CDCl3) delta: 1.37 (3H, s), 1.39 (3H, s), 5.38-5.47 (1H, m), 6.78 (1H, d), 7.43 (3H, m), 8.38 (1H, dd, J = 2.5, 8. 8 Hz), 8.52 (1H, d, J = 7.6 Hz), 8.96 (1H, d, J = 2.5 Hz).

The synthetic route of 195140-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 129747-52-0, 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 129747-52-0 as follows.

To a solution of the alcohol (655 mg, 3.92 mmol.) in DCM (7 mL) was added Dess-Martin periodinane (3.3 g, 7.84 mmol.). Stirred for 16h, then diethyl ether was added. The reaction was concentrated, and then partitioned between diethyl ether and a solution of sodium thiosulfate (6.8 g, 43.12 mmol.) in saturated NaHCO3 (50 mL). The aqueous layer was extracted using diethyl ether (2×). The combined organic extracts were dried with MgSO4 and concentrated. The crude product was purified by column chromatography to yield 6 (460 mg, 2.78 mmol, 71%). 1H-NMR (DMSO-d6): delta=10.03 (s, 1H), 8.33 (d, J=8Hz, 1H), 8.25 (dd, J=8 Hz+8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 3.95 (s, 3H). Calculated mass=165.1, [M]+=165.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,129747-52-0, its application will become more common.

Reference:
Patent; Wyeth; US2006/19965; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 870997-81-2, Adding some certain compound to certain chemical reactions, such as: 870997-81-2, name is 3-Amino-2-methoxy-4-pyridinecarboxylic acid,molecular formula is C7H8N2O3, 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 870997-81-2.

To a solution of 3-amino-2-methoxyisonicotinic acid (5.0 g, 29.7 mmol, Ark Pharm, Inc. – AK-39940) in dichloromethane (45 mL) and methanol (5 mL) at 0C was added trimethylsilyldiazomethane as 2.0M solution in hexanes (44.6 mL, 89.2 mmol) . After addition was complete, the reaction was quenched with water. The reaction mixture was extracted with dichloromethane. The organics were dried over sodium sulfate, filtered and concentrated down under reduced pressure to yield the compound 1a. 1H NMR (400 MHz, DMSO-d6) delta 7.29 (d, J = 5.6 Hz, 1 H), 7.1 1 (d, J = 5.6 Hz, 1 H), 6.45 (bs, 2H), 3.89 (s, 3H), 3.80 (s, 3H). LCMS (m/z) 183.0 [M+H], Tr = 1.21 min (LCMS method 1 ).

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. 870997-81-2, 3-Amino-2-methoxy-4-pyridinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; KVASNICA, Miroslav; MACKMAN, Richard, L.; (79 pag.)WO2016/105532; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71670-70-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, molecular formula is C7H9Cl2N, molecular weight is 178.06, as common compound, the synthetic route is as follows.

Step 3: 4-{[(5-Methylpyridin-2-yl)methyl]oxy}aniline dihydrochloride N-(4-Hydroxyphenyl)acetamide (25.0 kg) and potassium carbonate (50.0 kg) were mixed in ethanol (187.5 L) at 22±3 C. and 2-(chloromethyl)-5-methylpyridine hydrochloride (32.5 kg) was added portionwise at 22±3 C. The mixture was then heated to reflux for 15 h. The reaction was then cooled to 57±3 C. and water (162.5 L) added maintaining this temperature. The organic and aqueous phases were allowed to separate and the lower aqueous layer was removed. The organic layer was then washed with aqueous potassium carbonate (20% w/v, 114 kg) at 57±3 C. Sodium hydroxide (50% w/v, 57.8 kg) was then added together with ethanol (12.5 L) and the reaction stirred at reflux for about 38 h. The reaction was cooled to 57±3 C. and the lower aqueous phase was removed. The organic layer was concentrated to ~125 L by atmospheric distillation, 2-butanol (250 L) was then added and the concentration repeated. The reaction was then cooled to 22±3 C., further 2-butanol (125 L) was added and the mixture washed with water (75 L) at 50±3 C., followed by aqueous sodium chloride (5% w/w, 78 kg) at 50±3 C. The reaction was concentrated to 125 L by atmospheric distillation, further 2-butanol (125 L) was then added and the concentration repeated. 2-Propanol (150 L) was then added followed by hydrogen chloride (5 M -6 M in 2-propanol, 89.5 kg) over 2 hours at 76±3 C. The resulting slurry was then cooled to 22±3 C. over about 3.5 h, aged for about 40 min and the product isolated by filtration, washed with 2-propanol (2*200 L) follow by TBME (200 L) and dried at 40-50 C. under vacuum to give the title product (40.25 kg, 85% th). 1H NMR (400 MHz, DMSO-D6) deltappm 8.74 (1H, s); 8.28 (1H, dd, J=8.2, 1.3 Hz); 7.91 (1H, d, J=8.1 Hz); 7.38-7.42 (2H, m); 7.17-7.21 (2H, m); 5.46 (2H, s); 2.45 (3H, s).

Statistics shows that 71670-70-7 is playing an increasingly important role. we look forward to future research findings about 2-(Chloromethyl)-5-methylpyridine hydrochloride.

Reference:
Patent; Crawford, Claire Frances; Garcia, Sandrine; Graham, Jonathan Paul; Harling, Sandra Jane; Henley, Nicholas Paul; Hermitage, Stephen Andrew; Hutchinson, John Howard; Keel, Trevor Raymond; Kennedy, Andrew; Mason, Andrew McMurtrie; Scott, Mark Simon; Smith, Neil Michael; Stock, Nicholas Simon; Tateno, Yuichi; Trouw, Leontine Saskia; Turner, Peter Graham; Wallis, Christopher John; Willacy, Robert David; US2012/220779; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – 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. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Cyclopropylnicotinic acid

5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-{[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2- carbonitrile (102.8 mg, 0.25 mmol) was dissolved in DMF (4 mL), 6-cyclopropylnicotinic acid (62 mg, 0.38 mmol), DIPEA (0.2 mL, 1.26 mmol) and PyBOP (196 mg, 0.38 mmol) were added. The mixture was stirred at room temperature 1 h. Water and DCM were added and the mixture was extracted with DCM. The organic phase was dried over Na2SO4, filtered and evaporated to give a crude which was purified by silica flash chromatography with 50% to 100% ethyl acetate in cyclohexane to afford N-[(2R,3R)-1-(5-cyano-6-{[4-(oxan-4-yloxy)phenyl]amino}pyrazin-2- yl)-2-methylpiperidin-3-yl]-6-cyclopropylpyridine-3-carboxamide (120.7 mg, 87% yield) as a yellow solid. MS found for C31H35N7O3 as (M+H)+ 554.0.

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, 75893-75-3, 6-Cyclopropylnicotinic acid.

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem