Tag: M.W=100-200

Synthetic Route of 29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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.

Method A: 2,4-diamino-6-chloropyrido[3,2-c/]pyrimidine (7.5 g, 38 mmole), e.g. prepared according to Colbry et a/. J. Heterocycl, Chem. (1984) 21 :1521 , was suspended in 6 N HCI (300 ml) and the mixture was refluxed for 5 hours. After cooling, the pH was made alkaline (pH about 9 – 10) by means of 10 N NaOH. The precipitate obtained was filtered, washed with H2O and dried at 100 0C, resulting in the pure title compound (7.0 g, yield 95 %) which was characterized by its mass spectrum as follows: MS (m/z): 197 ([M+H]+, 100).Method B: A mixture of 3-amino-6-chloro-pyridine-2-carboxamide (5.1 g, 30 mmol), chloroform-amidine hydrochloride (6.99 g, 60 mmol), dimethylsulfone (24 g) and sulfolane (2.4 ml) was heated at 165 0C for 30 min. To the hot mixture was added water (50 ml). After cooling to room temperature, a diluted ammonium hydroxide solution was slowly added drop wise till pH 7. The resulting precipitate was filtered off, washed with water and dried overnight at 100 0C to give the pure title compound (5.8 g, 98 %). The obtained compound was used as such for further reactions without additional purification. M. p. >330C; elemental analysis calc. for C7H5CIN4O (196.6): C 42.77 H 2.56 N 28.50. Found: C 41.61 H 2.74 N 28.76.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Carbamimidic chloride hydrochloride, its application will become more common.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
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Electric Literature of 1303587-99-6,Some common heterocyclic compound, 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, molecular formula is C6H6ClN3O, 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.

Synthesis of (2-chloro-6, 7-dihydro-8H-pyrimido [5, 4-b] [I, 4] omicronchialphazetaeta-8-yl) (phenyl) methanone [0426] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (1.5 mL) under argon atmosphere were added sodium hydride (70 mg, 1.74 mmol) and benzoyl chloride (184 mg, 1.30 mmol) at 0C. The reaction mixture was stirred for 10 min at 0 C. After consumption of the starting materials (monitored by TLC), the reaction was quenched with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with a saturated sodium bicarbonate solution (20 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 35% EtOAc:hexanes to afford (2-chloro-6, 7- dihydro-8H-pyrimido [5, 4-b] [1, 4] oxazin-8-yl) (phenyl) methanone (160 mg, 66%>) as an off-white solid. 1H-NMR (CDC13, 500 MHz): delta 8.10 (s, 1H), 7.53-7.50 (m, 3H), 7.40-7.38 (m, 2H), 4.50-4.47 (m, 2H), 4.10-4.08 (m, 2H); LCMS: 276.3 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.89 min. 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 50% EtOAc:hexanes (R 0.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, its application will become more common.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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Synthetic Route of 33786-89-9, 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 33786-89-9 as follows.

DMAP (50 mg) and acetic anhydride (3.9 g, 37.9 mmol) were added sequentially and dropwise to a cold solution of 5-chloro-benzene-1 ,3-diamine (4.5 g, 31.6 mmol) in pyridine (22 ml.) keeping the internal temperature below 0C. The reaction mixture was allowed to warm to rt, stirred for 2 h, cooled to 0C, quenched by addition of ice cooled water, and extracted with EtOAc. The organic phase was washed with brine, dried (Na2S04), filtered, and concentrated. The crude material was purified by silica gel column chromatography (CH2CI2/MeOH, 99: 1 ) to afford the title compound. tR: 0.18 min (LC-MS 2); ESI-MS: 184.9 [M+H]+(LC-MS 2); Rf= 0.32 (hexane/EtOAc, 1 :4).

According to the analysis of related databases, 33786-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; MAH, Robert; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/80141; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2533-69-9, These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 4-bromobenzene-1,2-diamine (4.78 g, 25.5 mmol)in AcOH (50 mL) at 0C was added 5-bromo-2-(trichloromethyl)-1H-benzo[djimidazole (5.0 g, 28.3 mmol), then the mixture was stirred at room temperature for 3 hrs. Water was added and the precipitate was collected by filtration. The solid was washed with water, then dried under vacuum to afford the cmde product that was used directly in the next step without further purification. LC-MS (ESI): 312 (M + 1).

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
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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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, A new synthetic method of this compound is introduced below., Safety of 3,6-Dichloro-1,2,4,5-tetrazine

To a solution of 3,6-dichloro-1,2,4,5-tetrazine (1 g, 6.62 mmol) in Tol. (10 mL) was added pent-1-yn-3-ol (1.11 g, 13.25 mmol, 1.14 mL) at 20 C. The mixture was stirred at 110 C. for 16 hours under sealed tube. LCMS showed desired MS. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, petroleum ether:ethyl acetate=1:1) to give 32a. MS mass calculated for [M+1]+ (C7H8Cl2N2O) required m/z 207.1, LCMS found m/z 207.0; 1H NMR (400 MHz, CDCl3) delta 7.79 (s, 1H) 4.94 (dt, J=7.73, 3.77 Hz, 1H) 2.72 (d, J=4.03 Hz, 1H) 1.94 (dqd, J=14.52, 7.39, 7.39, 7.39, 3.55 Hz, 1H) 1.60-1.72 (m, 1H) 1.06 (t, J=7.34 Hz, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Terns, Inc.; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; ROMERO, F. Anthony; US2020/62742; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2,2,2-trichloroacetimidate

Step B4-bromo-2-(trichloromethyl)-6-[(trifluoromethyl)oxy]-1H-benzim[00346] A suspension of {2-amino-3-bromo-5-[(trifluoromethyl)oxy]phenyl}amine (2.08 g, 6.76 mmol) in acetic acid (35 mL) was treated with methyl 2,2,2-trichloroacetimidate (1.14 mL, 9.21 mmol), added dropwise via syringe. After stirring at rt overnight, the reaction mixture was diluted with water and extracted with diethyl ether (3x). The combined organic layers were washed with water (2x) and brine (1x), then dried over sodium sulfate and concentrated.Toluene was added and the mixture was concentrated under reduced pressure, then dried under vacuum to afford the title compound (2.54 g, 94%). LCMS: m/z 399 (M+1).

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 2533-69-9.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
Chloride – Wikipedia,
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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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., SDS of cas: 2106-04-9

Process step J+K, After 20 min at 50-60 C 1733 g 3-chloro-2-fluoranilin are added to the mixture. The dropping funnel is rinsed with 2 L acetonitrile. Then 7.8 kg 4 M hydrochloric acid in dioxane are added and the mixture is stirred for 45 mm at 55-80 C. After cooling to 1 C. the precipitate is filtered off and washed with 10 L ethanol. The precipitate is suspended in 40 L ethanol and combined with 290 g 3-chloro-2-fluoroaniline. The suspension is stirred for 45 min at 70-80 C and then for 13 h at RT. The precipitate is filtered off and washed with 10 L ethanol. After drying at 60 C in vacuo 4853 g of product is obtained as the hydrochloride.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; OSTERMEIER, Markus; SIEGER, Peter; WO2014/12859; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 20850-43-5, 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 20850-43-5 as follows.

General procedure: Suspension of the appropriate 3-amino-1,1-dioxo-1,4,2-benzodithiazine derivative 4a-h (0.5 mmol), anhydrous K2CO3 (1.5 mmol, 0.21 g) and the appropriate alkyl chloride (0.6 mmol) in dry THF (5 ml) was heated at reflux for 20-24 h, then cooled in ice-bath and filtered off. The crude product was suspended in 5 ml of water, heated gently to ca. 50 C; and cooled with vigorous stirring until granular precipitate appeared. Filtering off and washing with cold water and diluted EtOH gave pure potassium salts. 4.5.10 ;N-{2-[(1,3-Benzodioxol-5-yl)methylthio]-4-chloro-5-(4-(4-chlorophenyl)thiazol-2-yl)benzenesulfonyl}cyanamide potassium salt (5n) ;Starting from 4f (0.221 g) and 1,3-benzodioxol-5-ylmethyl chloride (0.102 g). Yield: 0.234 g (76%): m.p. 260-262 C; IR (KBr): nu 2895, 2185, 1635, 1578, 1503, 1488, 1472, 1361, 1285, 1142 cm-1; 1H NMR (500 MHz, DMSO-d6): delta 4.32 (s, 2H, SCH2), 6.00 (s, 2H, OCH2O), 6.87-6.89 (m, 1H, Ar), 6.96-6.97 (m, 1H, Ar), 7.04 (s, 1H, Ar), 7.55-7.57 (m, 2H, Ar), 7.60 (s, 1H, Ar), 8.06-8.08 (m, 2H, Ar), 8.41 (s, 1H, Ar), 8.77 (s, 1H, Ar); Anal. C24H14Cl2KN3O4S3 (C, H, N).

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brozewicz, Kamil; Slawinski, Jaroslaw; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 384 – 394;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 6775-78-6, These common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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.

Step 2: Preparation of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine (0530) (0531) 478 mg (3.11 mmol) of 6-chloroimidazo[1,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N-bromo-succinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions. (0532) 1H-NMR (CHLOROFORM-d): delta [ppm]=7.12 (d, 1H); 7.79 (s, 1H); 7.90, (d, 1H).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; EIS, Knut; PUEHLER, Florian; ZORN, Ludwig; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje Margret; PETERSEN, Kirstin; BOeMER, Ulf; (68 pag.)US2017/29441; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 57946-56-2, These common heterocyclic compound, 57946-56-2, name is 4-Chloro-2-fluoroaniline, 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 4-chloro-2-fluoroaniline (50.0 g, 344 mmol) in AcOH (3OmL) is added Ac2O (60 ml_) and the reaction is stirred at room temperature for 2 hours. The mixture is poured into ice water (500 mL) to give a solid precipitate. The mixture is stirred for an additional 1 hour at room temperature. The solid is filtered and washed with water and hexanes, then air dried to give lambda/-(4-chloro-2-fluorophenyl) acetamide

The synthetic route of 57946-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2008/2853; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics