Tag: M.W:100-200

Reference of 1020253-14-8, 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 1020253-14-8 as follows.

This compound (14 mg, 0.026 mmol, 26% yield) as a white solid was prepared in a fashion similar to that described for Example 116, here using 116a (42 mg, 0.101 mmol) and 6-chloro-5-fluoronicotinonitrile (24 mg, 0.151 mmol) as starting materials. LC/MS (ESI+) m/z = 538.1 [M+H]+. NMR (400 MHz, CHLOROFORM-d) delta ppm 8.66 (d, J = 2.54 Hz, 1H) 7.97 – 8.02 (m, 1H) 7.70 (dd, J = 7.14, 2.64 Hz, 1H) 7.58 – 7.65 (m, 1H) 7.1 1 (dd, J = 1 1.54, 8.61Hz, lH) 6.62 (d, J = 14.87 Hz, lH) 6.42 (d, J = 14.87 Hz, 1H) 4.58 – 4.92 (m,2H) 3.54 – 3.75 (m, 8 H) 2.10 (t, J = 8.31Hz, 1H) 1.41 (dd, J = 9.59, 5.87 Hz, 1H) 1.08 (t, J = 6.36 Hz, 1H). N peak was not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1020253-14-8, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); A1;,
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Pyridine | C5H5N – PubChem

Electric Literature of 4684-94-0, 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.4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

6-Chloropyridine-2-carboxylic acid (1.20 g, 7.62 mmol) and ammonium chloride (0.81 g, 15.2 mmol) were dissolved in DMF (20 mL) and DIPEA (5.31 mL, 30.5 mmol), HONB (2.05 g, 11.4 mmol) and HBTU (4.33 g, 11.4 mmol) were added. The reaction mixture was stirred for 1 h and the solvents were removed in vacuo. The residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL) and the aq fraction was extracted with DCM (2*25 mL). The combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH/water to give the title compound (1.12 g, 94%) as a white solid. LCMS (ES+): 157.4 [MH]+.

Statistics shows that 4684-94-0 is playing an increasingly important role. we look forward to future research findings about 6-Chloropicolinic acid.

Reference:
Patent; Proximagen Limited; Savory, Edward Daniel; Stewart, Allson; Cartey, Allison; Brown, Giles; Simpson, Iain; Oliver, Kathryn; Patient, Lee; Higginbottom, Michael; Cole, Andrew Graham; US2013/289020; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53554-20-4 ,Some common heterocyclic compound, 53554-20-4, molecular formula is C6H4ClN3, 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.

38 (1.00g crude, max 4.30mmol), diethylzinc (1.0M in hexane, 7.81mmol, 7.8mL), and Pd2(PPh3)4 (150mg, 0.13mmol) were added to a microwave vial along with NMP (8mL). The vial was flushed with N2, sealed and heated using microwave irradiation at 100C for 30min. The contents of the vial were cooled to rt and washed with sat. aq. NaHCO3 (120mL), and H2O (120mL), dried over Na2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 80:20 to 50:50) afforded the product as brown solid (333mg, 53% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.34 (d, J=8.5Hz, 1H), 4.99 (b s, 2H), 2.86 (q, J=7.6Hz, 2H), 1.31 (t, J=7.6Hz, 3H). 13C NMR (CDCl3) delta 167.4, 159.8, 141.4, 118.5, 105.7, 96.6, 30.4, 13.5.

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-35-8 , The common heterocyclic compound, 13466-35-8, name is 3-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, 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 500 ml four-necked flask equipped with a thermometer, mechanical stirring, and a reflux condenser was added 150 g of 1,2-dichloroethane, 26.0 g (0.2 mol) of 2-hydroxy-3-chloropyridine prepared in Example 3, 52.0 g (0.25 mole) of phosphorus pentachloride, stir the reaction at 60-65 C for 10 hours, then slowly pour the residue into 200 g of ice water, stir well, and then neutralize the pH value with a 40 wt% sodium hydroxide aqueous solution. 8. The layers were separated. The aqueous layer was 50g with 1,2-dichloroethane three times. The organic phases were combined, washed with 30g of saturated brine, and then dried with 5g of anhydrous sodium sulfate. The solvent was removed by rotary evaporation. 28.1 g of 2,3-dichloropyridine (I) with a yield of 94.9% and a gas phase purity of 99.9%.

The synthetic route of 13466-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Sun Yulong; Zhang Mingfeng; Chang Renyi; Wang Tao; (10 pag.)CN110818622; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1314353-68-8, 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. 1314353-68-8, name is 5-Cyclopropylpyridin-3-amine, molecular formula is C8H10N2, 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.

3-Amino-5-cyclopropylpyridine obtained in the above-described Step 1 (67 mg) and p-toluenesulfonic acid monohydrate (10 mg) were added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (70 mg) in DMF (1 ml), and the reaction solution was stirred in a microwave reactor at 100C for 30 minutes. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution, water, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent: hexane/ethyl acetate) to obtain ethyl 5-(5-cyclopropylpyridin-3-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate as a white solid.

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 1314353-68-8, 5-Cyclopropylpyridin-3-amine.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAKAMOTO, Toshihiro; MITA, Takashi; SHIBATA, Kazuaki; OGINO, Yoshio; KOMATANI, Hideya; EP2762476; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 780800-73-9, 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. 780800-73-9, name is (3-Isopropylpyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

To a vigorously stirred solution of (3-isopropyl-pyridin-2-yl)-methanol (26 g, 170 mmol) in CH2Cl2 (575 mL) was added manganese(IV) oxide (105 g, 1.20 mol) under N2. The mixture was stirred for 18 h then filtered through a celite pad and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc/hexanes, 1:3) afforded 3-isopropyl-pyridine-2-carbaldehyde (15.65 g, 61%) as an orange oil. 1H NMR (CDCl3) delta 1.26 (d, 6H, J=7.0 Hz), 4.17 (sep, 1H, J=6.6 Hz) 7.45 (dd, 1H, J=7.9, 4.4 Hz), 7.84 (d, 1H, J=7.9 Hz), 8.56 (dd, 1H, J=4.4, 1.3 Hz), 10.2 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,780800-73-9, (3-Isopropylpyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Bridger, Gary; McEachern, Ernest J.; Skerlj, Renato; Schols, Dominique; US2004/209921; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9, 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 72587-18-9 as follows.

6-chloro-3- (ethanesulfonyl) pyridin-2-carboxylic acid 2.50 g, and the mixture of thionyl chloride 1.31g of toluene 30 mL, and DMF1 drop was heated under reflux for 3 hours. The reaction mixture was concentrated and dissolved in tetrahydrofuran 30 mL, under ice-cooling, 3-amino-2-chloro-5- (trifluoromethyl) pyridine 1.97 g, triethylamine 1.10g was added dropwise respectively. After stirring for 3 hours at room temperature, The reaction mixture was added to ice water, and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, described below 6-chloro-3- (ethanesulfonyl) – [2-chloro-5- (trifluoromethyl) pyridin-3-yl] pyridine-2-carboxamide 2.4g It was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72587-18-9, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

[N- (5-CYANO-2-PHENYL-LH-PYRROLOF2, 3-BLPYRIDIN-3-YL)-ACETAMIDE] [6-CHLORO-NICOTINONITRILE] (1.38 g, 10 mmol) was dissolved in 1,4-dioxane (50 ml). Hydrazine hydrate (0.525 ml, 10.4 mmol) was added and the resulting solution stirred for 1.5h, whereupon it was concentrated in vacuo. The residue was chromatographed (silica gel, gradient ethyl acetate/heptane from 1: 1 to 1: 0). The slower running component was concentrated in vacuo to afford the 6-hydrazino-nicotinonitrile monohydrate [0.80 g, 53%, APCI-MS m/z: 135.2 [MH+] ]. Part of this hydrazine (67 mg, 0.5 mmol) and [N- (2-OXO-2-] [PHENYL-ETHYL)-ACETAMIDE] (85 mg, 0.5 mmol) were fused together for lh at 230 [C.] The reaction mixture was allowed to cool and the glassy solid suspended in warm dichloromethane/methanol (7: 3 mixture) and then filtered. The solid was further washed with hot [ACETONITRILE/N,] [N-DIMETHYLFORMAMIDE] (9: 1 mixture) and finally acetonitrile. This afforded the title compound as a grey powder (25 mg, 18%). ‘H-NMR (DMSO-d6) : [B] 12.64 [(1H,] s); 9.66 [(1H,] s); 8.62 [(1H,] s); 8.27 (1H, s); 7.84 (2H, d); 7.52 (2H, t); 7.42 [(1H,] t); 2.10 (3H, s). [‘3C-NMR] (DMSO-d6) : [8] 147.3 ; 145.8 ; 134.0 ; 131.5 ; 129.9 ; 128.8 ; 128.7 ; 127.5 ; 118.8 ; 117.6 ; 110.1 ; 99.9 ; [22. 7.] APCI-MS m/z : 277.1 [[MH+].]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2004/16609; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-26-6, 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 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
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. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol, molecular formula is C6H6BrNO, 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. COA of Formula: C6H6BrNO

To a mechanically-stirred solution of 78.12 g of thionyl chloride in 450 mL of acetonitrile at 15 C. was added a solution of 160.75 g of 3-hydroxymethyl-6-bromopyridine in 446 mL of acetonitrile over 30 minutes. The temperature rose to 22 C. during the addition, and the reaction mixture was stirred for 15 minutes at room temperature. The mixture was cooled in an ice bath, and a solution of 70 g of NaOH in 1.4 L of water was added at such a rate that the temperature did not exceed 15 C. 603 mL of toluene was added to the mixture and stirred rapidly. The layers were separated. The aqueous phase was reextracted with toluene. The combined organic phase was concentrated in vacuo to give 181.61 g of 3-chloromethyl-6-bromopyridine.

With the rapid development of chemical substances, we look forward to future research findings about 122306-01-8.

Reference:
Patent; G. D. Searle & Co.; US5420270; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem