Day: June 15, 2021

Adding a certain compound to certain chemical reactions, such as: 86873-60-1, 5-Chloro-2-picolinic acid, 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, Application In Synthesis of 5-Chloro-2-picolinic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Chloro-2-picolinic acid

To a stirred solution of tert-butyl (l-aminopiperidin-4-yl)carbamate (500 mg, 2.32 mmol, 1.0 equiv) in DMF (05 mL) was added HATU (1763 mg, 4.64 mmol, 2.0 equiv) at RT and stirred for 10 minutes Then 5-chloropicolinic acid (365 rng, 2.32 mmol, 1.0 equiv) was added followed by the addition of DIPEA (1.2 mL, 6.96 mmol, 3.0 equiv). The resulting reaction mixture was allowed to stir at RT for overnight. Product formation was confirmed by LCMS. the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL c 2). The combined organic layer was washed with water (30mL), brine solution (30 mL x 2), dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain tert-butyl (l-(5- chloropicolinamido)piperidin-4-yl)carbamate (500 mg, 60 % Yield) as an off white solid. LCMS 355.1 [M+H]+; i XMR (400 MHz. DMSO-cA) d 9.61 (s, 1 H), 8.66 (d, J=2.19 Hz, 1 H), 8.11 (dd, J==8.33, 2.19 Hz, 1 H), 7.99 id. =8.33 Hz, 1 H), 6.83 (d, ./ 7.02 Hz, 1 H), 3.23 (br. s., 1 H), 2.84 – 3.00 (m, 3 H), 2.62 – 2.84 (m, 2 H), 1 73 (d, J=l 1.40 Hz, 2 H), 1.47 – 1.66 (m, 2 H), 1 38 (s. 9 1 1}

The synthetic route of 86873-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS BIOTECH LLC; DELGADO OYARZO, Luz Marina; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; (0 pag.)WO2019/236710; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8, 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

Example : 8; 8- (2-isobutoxybenzyl)-2- (pyridin-2-ylacetyl)-2, 8-diazaspiro [4.5] decane; Scheme 1; a) tert-butyl 2- (pyridin-2-ylacetyl)-2, 8-diazaspiro [4.5] decane-8-carboxylate; To a solution of tert-butyl 2,8-diazaspiro [4.5] decane-8-carboxylate hydrochloride (800mg, 2. 89mmol, 1 equiv), 2-pyridylacetic acid hydrochloride (500mg, 2. 89mmol, 1 equiv) and triethylamine (1. 2ml, 8. 68mmol, 3 equiv) in dry dichloromethane (12ml), was added 0-(7-azabenzotriazol-1-yl)-N, N, N, N’-tetramethyluronium hexafluorophosphate (1. 1 g, 2.89mmol, 1 equiv). The reaction mixture was stirred at room temperature for 3 hours, then concentrated, and partitioned between ethyl acetate and saturated sodium hydrogen carbonate. The organic layer was isolated, dried (MgS04) and concentrated to give a dark orange oil which was subjected to silica-gel chromatography using a mixture of methanol and dichloromethane (4: 96, v/v) as eluent, to provide the title compound (1.2g, quantitative) as a dark yellow oil. LCMS (Method E): RT = 2.19 minutes; 360 (M+H) +.

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 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride.

Reference:
Patent; ASTRAZENECA AB; WO2005/40167; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83004-10-8, 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.83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at O0C, followed by stirring the reaction mixture at 00C for 30 minutes. After cooling down to -78C, a solution of 1.54 g of 1- tert-butyl 4-ethyl piperidine-l,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at -78C for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at -78C for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 20/1 – 2/1) to give the title compound as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 83004-10-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; WO2009/104802; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183208-35-7, Adding some certain compound to certain chemical reactions, such as: 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 183208-35-7.

Preparative Example 6 Step 1: l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone To a soluition of 5-bromo-lH-pyrrolo[2,3-b]pyridine(30 g, 0.15 mol) and aluminium chloride (100 g, 0.75 mol) in dichloromethane (2000 mL) was added dropwise acetyl chloride (102 mL, 1.44 mol) over 1 h under nitrogen atmosphere at 0 C. The reaction mixture was warmed to RT and stirred overnight. Methanol (150 mL) was added dropwise at 0 C, and the resulting mixture was concentrated to dryness in vacuo. The resulting crude was dissolved in ice -water, basified with saturated sodium bicarbonate to pH 4 – 5 and extracted with ethyl acetated (3 x 3000 mL). The combined organic layer were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as a yellow solid (330 g, 93 % after 10 batch repeat) used for the next step without any further purification: lH NMR (DMSO, 400 MHz): delta 12.675 (s, 1H), 8.537-8.543 (d, = 2.4 Hz, 1H), 8.506 (s, 1H), 8.371- 8.377 (d, J = 2.4 Hz, 1H), 2.445 (s, 3H).

According to the analysis of related databases, 183208-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloromethyl-3,4-dimethoxypyridinium chloride

10% NaOH solution (42.5 gm in 425 ml of water) is added drop wise to a solution of 5-(difluoromethoxy)-2-mercapto benzimidazole (100.0 gm; 0.462 moles) in methanol(350.0 ml) at 10-150C. To the above solution a clear solution of 2-chloro-3, 4-dimethoxy pyridine hydrochloride (105.5 gm.0.473 moles in 525 ml of methanol) was added at 10-150C. The reaction mass was maintained at 10-15C for 30 minutes. The temperature of the reaction mass was slowly raised to 2O0C. The reaction mass was maintained at 20-25 C for 2 hours. Further the temperature was raised to 400C and maintained at 400C. Completion of the reaction is monitored by TLC. After completion of the reaction methanol is evaporated under reduced pressure to get a residue. Chilled water (600 ml) was added to the residue and the reaction mass was extracted with methylene chloride (600 ml, 300 ml x 2). The organic layers were separated and evaporated under reduced pressure to obtain a residue. Isopropyl alcohol (50 ml) and hexane (600 ml) were added to the reaction mass. The reaction mass was cooled to 0-50C and maintained at 0-5C for 30 minutes. The reaction mass was filtered at 0-5C and washed with chilled hexane (100 ml). The solids were dried under vacuum at 4O0C; Dry wt-162 gm (Yield=95.3%); HPLC Purity=99.21% w/w.; Melting range=l 15-1170C (Lit.7mp-H5-1 18C); MS (ESI); 368.0(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, 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride.

Reference:
Patent; MACLEODS PHARMACEUTICALS LIMITED; WO2009/66317; (2009); A2;,
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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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. SDS of cas: 183610-70-0

In a 7 ml screw cap vial 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.10 g, 0.31 mmol), DMF (1 ml) and 3-(trifluoromethyl)-2-pyridinamine (0.076 g, 0.47 mmol) were added and the resulting mixture stirred at 80 C. for 13 h. The mixture was eluted through a SCX column. Collected fractions gave 0.15 g of a crude containing the title compound D7, the corresponding free amine and some residual 3-(trifluoromethyl)-2-pyridinamine. The material was used in the next step without further purification. HPLC (walk-up): rt=3.79 min. MS: (ES/+) m/z: 384 (M+1). C19H24F3N3O2 requires 383.

With the rapid development of chemical substances, we look forward to future research findings about 183610-70-0.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, molecular weight is 182.44, as common compound, the synthetic route is as follows.Recommanded Product: 2,4,6-Trichloropyridine

To a 15 mL vial equiped with a stir bar was added 2,4,6-trichloropyridine (365 mg, 2.00 mmol) and Pd(dppf)Cl2 (146 mg, 0.200 mmol). The vial was sealed with a septum screwcap and then was placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (10.0 mL, 5.00 mmol). The vial was placed in a 60 C heating block with stirring for 16 h. The reaction mixture was cooled to room temperature, and then was transfered to a 125 mL separatory funnel where it was diluted with Et20 (50 mL) and water (50 mL). The mixture was filtered to remove a significant amount of a yellow-white precipitate and the filtrate was returned to the separatory funnel. The phases were isolated and the aqueous phase was extracted with EtOAc (25 mL). The combined organics were washed with brine (50 mL); dried over MgS04; filtered; then concentrated in vacuo to afford a pale yellow solid which was subjected to silica gel chromatography (CH2Ci2:MeOH, 100:0 to 90: 10) to afford 2,2′-(4-chloropyridine-2,6-diyl)dithiazole as a white solid (294 mg, 53%). 1H-NMR (400MHz, CDC13) delta 8.23 (s, 2H), 7.97 (d, J=3.0 Hz, 2H), 7.53 (d, J=3.3 Hz, 2H); MS: MS m/z 280.0 (M++l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16063-69-7, 2,4,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLIS, Eric P.; BOWSHER, Michael S.; SCOLA, Paul Michael; WO2014/71007; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1173081-96-3 , The common heterocyclic compound, 1173081-96-3, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride, molecular formula is C8H13ClN2O, 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 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid (1.06 g, 2.25 mmol) in DMSO (5.8 mL) at rt was added triethylamine (0.90 mL, 6.44 mmol) and (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methanaminium chloride (0.405 g, 2.15 mmol). The clear solution become heterogenous. Then HOBT (0.493 g, 3.22 mmol) and EDC (0.617 g, 3.22 mmol) were added and the resulting reaction mixture was stirred at rt overnight. The reaction was quenched with water (80 mL) and the slurry was stirred for 1 h at rt. The slurry was filtrated and the cake was washed with water (2*20 mL). The collected solid was dried under vacuum to give the titled compound (1.27 g, 98% yield). 1H-NMR (500 MHz, CD3OD) 8 ppm; 7.22 (s, 1H), 7.08 (d, J=1.0 Hz 1H), 6.11 (s, 1H), 4.45 (s, 2H), 3.92 (brd, J=10.8 Hz, 2H), 3.78 (dd, J=4.4, 5.4 Hz, 1H), 3.75 (dd, J=4.4, 5.4 Hz, 1H), 3.36 (t, J=11.7 Hz, 2H), 3.21 (br t, J=8.3 Hz, 2H), 3.07 (q, J=7.3 Hz, 2H), 3.01 (dddd, J=3.9, 3.9, 11.3, 11.3 Hz, 1H), 2.84 (dddd, J=3.4, 3.4. 3.9, 3.9 Hz, 1H), 2.38 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H), 1.88 (m, 2H), 1.70 ((brd, J=12.2 Hz, 2H), 1.60 (m, 4H), 1.47 (s, 9H), 0.87 (t, J=7.3 Hz, 3H); MS (ESI) [M+H]+605.6.

The synthetic route of 1173081-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuntz, Kevin Wayne; Campbell, John Emmerson; Seki, Masashi; US2014/107122; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 160599-70-2, 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. 160599-70-2, name is 2,5-Dibromo-3-chloropyridine, molecular formula is C5H2Br2ClN, 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 pressure vessel was charged with 4,4,5, 5-tetramethyl-2-(4- (phenylsulfonyl)phenyl)-l,3,2-dioxaborolane (6.34 g, 18.43 mmol), 2,5-dibromo- 3-chloropyridine (5.00 g, 18.43 mmol, Sigma-Aldrich, St. Louis, MO), potassium carbonate (7.64 g, 55.3 mmol), tetrakis(triphenylphosphine)palladium (1.06 g, 0.92 mmol, Strem Chemical Inc, Newburyport, MA), 20 mL of 1,2- dimethoxy ethane, and 4 mL of water. The vessel was sealed and the reaction mixture was heated at 100 C for 8 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL) and water. The layers were separated and the organic phase was dried (MgS04), filtered, and concentrated under a vacuum to give an oil. Purification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes) produced 5-bromo-3-chloro-2-(4- (phenylsulfonyl)phenyl)pyridine (2.56 g) as a tan solid.

According to the analysis of related databases, 160599-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 695-34-1, 4-Methylpyridin-2-amine, 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, COA of Formula: C6H8N2, blongs to pyridine-derivatives compound. COA of Formula: C6H8N2

In a nitrogen atmosphere, 1.08 g of 2-amino-4-methylpyridine was dissolved in 75 mL of tetrahydrofuran, and tetrahydrofuran (75 mL) solution of 3.20 g of pyridinium hydrobromide perbromide was dropwise added thereto at room temperature, over 1.5 hours. After the addition, this was stirred at room temperature for 40 minutes, and 100 mL of aqueous saturated sodium sulfite solution was added to the reaction mixture. This was extracted with ethyl acetate, and the ethyl acetate layer was dried with magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate = 4/1 to ethyl acetate) to obtain 1.00 g of the entitled compound as a white solid.

The synthetic route of 695-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726590; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem