Month: May 2021

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. 18112-31-7, name is 3-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrClN3

A mixture of 50 mg (0.203 mmol) of 3-Bromo-6-chloro-2-methyl-imidazo[1 ,2-b]pyridazine (BKS422; preparation see Stage 61.1 ), 92 mg (0.446 mmol) of (4-methylsulfonyl)- EPO phenylboronic acid (Combi-Blocks), 0.51 ml of a aqueous 1 M K2CO3-solution, 8 mg of Pd(PPh3)2CI2 in 1.5 ml of DMF are heated in an oil bath at 1050C for 5 h. The reaction mixture is ppured into CH2CI2, washed with water and dried (Na2SO4). After the solvent is evaporated, the residue is purified by chromatography on silicagel. Solvent system: CH2CI2- EtOAc = 100-0 (start) to 0/100 (end). The title compound is isolated as a yellow solid. MS: 442 (M+1 ); HPLC: tR = 3.71 Omin.

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 18112-31-7.

Reference:
Patent; NOVARTIS AG; WO2008/52733; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 320-50-3, 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 320-50-3 as follows.

Similarly, 4-(2-trifluoromethyl-4-chlorophenoxy)benzene is prepared by following the same procedure but using 1,4-dichloro-2-trifluoromethylbenzene in place of 1,2-dichloro-4-trifluoromethylbenzene.

According to the analysis of related databases, 320-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chevron Research; US4289909; (1981); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1298031-94-3, A common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 dry three-necked round-bottomed flask at -78C under inert atmosphere was charged with anhydrous THF (20 mL). A solution of n-butyllithium (2.5 M in hexane, 26.1 mL, 65.3 mmol) was added dropwise, followed by addition of anhydrous acetonitrile (4 mL, 65.3 mmol). The internal temperature was maintained below -70 C during the entire addition process. After stirring 30 min at -78 C, a solution of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (2.0 g, 8.2 mmol, prepared according to Example 43) in anhydrous THF (20 mL) was added drop- wise. The mixture was stirred for 2 h at -78 C. The excess reagent was quenched carefully with sat’d aqueous NH4C1. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 2-(6-chloro- 2-methylimidazo[l,2-b]pyridazin-8-yl)acetonitrile (1.2 g, 71%). MS m/z 207.1, 209.1 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924818-16-6, name is (5-Chloro-2,4-difluorophenyl)methanamine, belongs to chlorides-buliding-blocks compound, 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 924818-16-6, Product Details of 924818-16-6

N-(5-Chloro-2,4-difluorobenzyl)-2,2-dimethoxyacetamide; A mixture of methyl dimethoxyacetate (1.45 g, 10.7 mmol) and 5-chloro-2,4-difluorobenzylamine (1.78 g, 10.0 mmol) in a sealed tube was heated at 80¡ã C. for 20 h. After that time, the mixture was diluted with EtOAc (20 ml), washed with HCl (2 N, 10 ml), saturated Na2CO3 (10 ml), H2O (10 ml) and brine (10 ml), and dried over MgSO4. After concentrated in vacuo, the title compound was obtained as a brown oil. 1H NMR (400 MHz, CDCl3): delta=3.41 (s, 6 H), 4.46 (d, J=6.4 Hz, 2H), 4.74 (s, 1H), 6.92 (t, J=8.8 Hz, 1H), 6.93 (brs, 1H), 7.41 (t, J=8.0 Hz, 1H). MS(ES+): m/z=280.03/282.01 (95/57) [MH+]. HPLC: tR=3.02 min (polar-5 min, ZQ3).

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.

Reference:
Patent; OSI Pharmaceuticals, Inc.; US2009/197862; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4261-67-0, 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. 4261-67-0 name is 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, This 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 3 Cis(+)-3-acetyloxy-2,3-dihydro-5-(2-methyl-3-dimethylaminopropyl)-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one oxalate (diastereoisomer B) 5 g cis(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one, 2.9 g 2-methyl-3-dimethylaminopropylchloride hydrochloride, 5.7 g K2 CO3, 1.4 ml H2 O were reacted in 75 ml acetone, according to the procedure as in Example 1 (a), then reacted with 70 ml acetic anhydride, (see Example 1 (b)). The crude was treated with ethyl ether and the so obtained solid is filtered off and the solution was evaporated to dryness. This procedure was repeated. 4.3 g residue were dissolved in isopropyl alcohol and treated with 1.2 g oxalic acid. A solid, which was crystallized from acetone-ethyl ether, was obtained; m.p. 84¡ã-89¡ã C.; [alpha]D20 =119.3 (H2 O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Istituto Luso Farmaco d’Italia S.p.A.; US5571807; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 445-01-2,Some common heterocyclic compound, 445-01-2, name is 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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.

PREPARATION 4 1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine-4-ol (Prepared according to Collection Czechoslav. Chem. Commun. 1973, 38, 3879) A solution of 5-Bromo-2-chlorobenzotrifluoride (5 g, 19.2 mmol) in dry diethyl ether (40 ml) was added dropwise at room temperature to a mixture of Mg (470 mg) in dry diethyl ether (20 ml) under a stream of Argon (g). The reaction gave rise to a solution of Grignard’s reagent. A solution of 1-benzyl-4-piperidone (1.3 g, 6.88 mmol) in dry diethyl ether (30 ml) was added dropwise via syringe at room temperature. The combined mixture was stirred for 1 hour, and finally quenched with saturated ammonium chloride solution (40 ml). The mixture was extracted several times with EtOAc and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The oily residue was chromathographed on a silica column using EtOAc:toluene (1:1 (v/v)) as eluent affording the title compound (1.6 g, 64%). MS m/z (relative intensity, 70 eV) 369 (M+, 23), 278 (15), 91 (bp), 65 (16), 56 (21).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Sonesson, Clas; Andersson, Bengt; Waters, Susanna; Waters, Nicholas; Tedroff, Joakim; US2003/4169; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 90390-33-3,Some common heterocyclic compound, 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, molecular formula is C7H7ClFN, 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.

3.2 1 -l3enzyl-3-hydroxypyrrolidine-3-carboxylic acid (100mg) and 3-chloro-5-fluorobenzylamine (79 mg) are dissolved in one millilitre of dried DM50 and cooled to 0C. o-(7-Azabenzotrial-l -yl)-N,N,N?,N?-tetramethyluroniumhexafluorophosphate (206 mg) and 4-methylmorpholine (0.124 ml) are then added. The batch is stirred at 25 C. for 2 hours and then immediately purified by chromatography, giving N-(3-chloro-5-fluorobenzyl)-l -benzyl-3-hydroxypyrro- lidine-3-carboxamide (37 mg) as colourless amorphous solid.

The synthetic route of 90390-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7ClFN

The compound of intermediate 2 (122 mg, 535 mumomicronIota) was provided in DMF (1.5 mL). N,N-diisopropylethylamine (280 mu, 1.6 mmol), propane phosphonic acid anhydride (T3P, 470 mu, 50% in DMF, 800 mumomicronIota) and 1-(3-chloro-5-fluorophenyl)methanamine (128 mg, 802 mumomicronIota) were added, and the mixture was stirred at room temperature for 4 days. After concentration, the remaining material was triturated with ethanol and water and the mixture was stirred for 15 minutes. The precipitate was collected by filtration, and was dried under reduced pressure. 156 mg (76% of theory) of the title compound were obtained. LC-MS (method 2): Rt = 1.12 min; MS (ESIpos): m/z = 370 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 2.323 (0.77), 2.327 (1.12), 2.332 (0.77), 2.523 (2.87), 2.665 (0.83), 2.669 (1.10), 2.674 (0.79), 2.729 (1.58), 2.889 (2.01), 4.481 (9.75), 4.496 (9.57), 7.167 (2.39), 7.174 (3.41), 7.177 (2.74), 7.191 (2.58), 7.195 (3.49), 7.198 (3.56), 7.201 (3.44), 7.205 (1.69), 7.219 (5.21), 7.224 (8.57), 7.233 (8.41), 7.242 (9.14), 7.247 (5.78), 7.260 (2.05), 7.272 (4.61), 7.277 (8.15), 7.280 (5.04), 7.313 (2.86), 7.318 (4.09), 7.324 (2.31), 7.335 (2.91), 7.341 (4.03), 7.346 (2.29), 7.457 (0.65), 7.466 (4.06), 7.470 (3.35), 7.476 (2.58), 7.483 (3.11), 7.489 (3.27), 7.500 (0.48), 7.597 (0.57), 7.607 (3.75), 7.613 (3.15), 7.620 (2.44), 7.626 (2.94), 7.630 (3.32), 7.638 (0.53), 7.823 (0.57), 8.306 (16.00), 8.986 (2.34), 9.001 (4.83), 9.015 (2.25), 9.138 (15.50), 13.287 (5.95).

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; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; ZORN, Ludwig; STEIGEMANN, Patrick; GRUeNEWALD, Sylvia; ALGIRE, Carolyn; NEUHAUS, Roland; CHRISTIAN, Sven; GUeNTHER, Judith; KOPPITZ, Marcus; SCHWEDE, Wolfgang; (78 pag.)WO2016/202756; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33050-36-1, 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. 33050-36-1 name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, This 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-Mercapto-s-triazolo[4,3-b]pyridazine A mixture of 1.20 g. (8 mmole) of 3-chloro-s-triazolo[4,3-b]pyridazine [P. Francavilla and F. Lauvia, J. Het. Chem., 8, 415 (1971) and 120 g. (16 mmole) of KSH in 20 ml. of ethanol was heated for 8 hours at 130 in a sealed tube. After cooling the mixture was evaporated to dryness and the residue was dissolved in 100 ml. of water, treated with active carbon, acidified to pH 1 with dil. HCl to precipitate 3-mercapto-s-triazolo[4,3-b]pyridazine which was collected, washed with 10 ml. of water and dried in vacuo over P2 O5 to yield 0.75 g. (62%), m.p. 260-270 (dec.). IR: nu maxKBr 3080, 2940, 2760, 1620, 1500, 1280, 1055 cm-1. NMR: ? ppmDMSO-d6 6.99 (1 H, d-d, 4 & 10 Hz, 7-H), 7.67 (1 H, d-d, 2 & 10 Hz, 8-H), 8.15 (1 H, d-d, 2 & 4 Hz, 6-H), 12.3 (1 H, br-s, disappear by addition of D2 O). Anal. Calcd. for C5 H4 N4 S. 1/2H2 O: C, 37.26; H, 3.13; N, 34.76. Found: C, 37.35; H, 2.32; N, 34.81.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Company; US3946000; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, belongs to chlorides-buliding-blocks compound, 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 121-27-7, Formula: C12H9Cl2NO

EXAMPLE IV-3 STR526 A solution of 27.6 g (0.4 mol) of sodium nitrite in 31.7 ml of water is added dropwise with stirring at 0 C. to 5 C. to 84.3 g (0.3 mol) of 5-chloro-2-(4-chlorophenoxy)aniline (compare, for example, EP No. 34,771), 284 ml of water and 72.2 ml of concentrated hydrochloric acid, the mixture is stirred for a further 15 minutes after completion of the addition and filtered, 16.4 g (0.2 mol) of sodium acetate are added to the filtrate and the solution thus obtainable is added dropwise with stirring at 10 C. to 15 C. to a mixture of 253 ml of water, 123 g (1.5 mol) of sodium acetate, 2.5 g (0.015 mol) of sodium sulphate, 15.9 g (0.1 mol) of copper(II) sulphate and 28.3 g (0.48 mol) of acetaldoxime. After completion of the addition, the mixture is stirred for one hour at room temperature, the pH is then adjusted to 7 by addition of about 40 ml of concentrated hydrochloric acid, 292 ml of concentrated hydrochloric acid are then added in portions and the mixture is heated to reflux temperature for 3 hours. The reaction mixture is subjected to a steam distillation, the oil which separates is taken up in dichloromethane, and the solution is dried over sodium sulphate, concentrated and distilled in a high vacuum. 29.5 g (35% of theory) of 5-chloro-2-(4-chlorophenoxy)acetophenone of boiling point 80-85 C. at 1.5 mbar are obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2-(4-chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; US4956370; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics