Month: June 2021

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. 2401-24-3, name is 2-Chloro-5-methoxyaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8ClNO

Preparation of (2-Chloro-5-methoxy-phenyl)-urea (Intermediate 5) A solution of 2-chloro-5-methoxyaniline (5 g, 25.76 mmol) and potassium cyanate (5.22 g, 64.41 mmol) in a mixture of acetic acid (125 mL) and water (12.5 mL) was stirred at room temperature overnight. The solvent was evaporated, and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The layers were separated, the aqueous one being extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography on silica gel (cyclohexane/EtOAc/MeOH: 80/20/2) to give 2.06 g (40%) of intermediate 5. 1H NMR [(CD3)2SO] delta7.97 (br s, 1H, NH), 7.85 (d, J=3.0 Hz, 1H), 7.27 (d, J=9.0 Hz, 1H), 6.54 (dd, J=9.0, 3.0 Hz, 1H), 6.4-(br s, 2H), 3.71 (s, 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; Bernardelli, Patrick; Ducrot, Pierre; Lorthiois, Edwige; Vergne, Fabrice; US2002/198198; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

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, 4-Chloro-3-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

To a solution of 2-bromo-4-chloro-l-fluoro-benzene (5 g, 0.0238 mol) in anhydrous diethyl ether (30 mL) was added a 2M solution of n-BuLi in n-hexane (13 mL, 0.0262 mol) at -70 C under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 30 min. Then, to this reaction mixture was added triisopropyl borate (4.93 g, 0.0262 mol) dropwise. The reaction mixture turned into a white slurry, which was further stirred at -70 C for 30 min and then warmed to RT and stirred for 1 h. The progress of reaction was monitored by TLC and 1H NMR. After completion of the reaction, the mixture was hydro lyzed with 6 N HC1, stirred for lh and the product was extracted with EtOAc (50 mL). The organic layer was washed with brine and concentrated under reduced pressure to obtain a sticky compound which was triturated with n-pentane to afford (5-chloro-2-fluoro-phenyl)boronic acid (2.2 g) as an off white solid

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; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, 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 1009102-44-6 as follows.

To a soution of (E)-3-((3aS,5aR,5bR,7aR,9S, 11 aR, 11 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8, 11 a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a, 11b, 12,13, 13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylic acid (500 mg, 1.007 mmol), 1-(4- chlorophenyl)cyclopropanamine hydrochloride (226 mg, 1.107 mmol) and HATU (765 mg, 2.013 mmol) in Nu,Nu-dimethylformamide (DMF) (2 mL) stirred at 0C was added DIPEA (0.703 mL, 4.03 mmol) . The reaction mixture was stirred at 20 C for 1 h. The reaction mixture was adjusted pH to 3-4 by 2 M HCI, filtered, and the solid was washed with water (50 mL), solved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude product. The crude product was washed with petrol ether/EtOAc/DCM (10/1/1) to afford the target product (E)-N-(1-(4-chlorophenyl)cyclopropyl)-3- ((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a, 5b, 8,8,11 a- pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9, 10,11, 11a, 11b, 12, 13,13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylamide (685 mg, 1.007 mmol, 100 %)) as a yellow soild.

According to the analysis of related databases, 1009102-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian Alvin; TANG, Jun; WO2013/90683; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 2,2,6,6-tetramethylpiperidine (92 uL, 0.54mmol) in THF (4 mL)at -10C, R-BuLi (338 uL, 1.6M in hexane, 0.54mmol) was added drop wise and thereaction mixture was stirred at -10C for 10 min. Compound 33 (60mg, 0.36mmol) [G. B.Evans et al. J. Ore. Chem.. 2001. 66.17. 5723-5730 and shown in the scheme 6] was addeddrop wise maintaining the temperature below -70C over a period of 15 min. Dried CC^-gaswas bubbled through the reaction mixture and stirred at room temperature overnight. Theprecipitate thus formed was collected by filtration and dried to afford the title compound275 (78mg, 100% yield) as a yellow solid. MS (m/z): 209.9 (RCOOH, M-H) (found).Step 2. 4-Chloro-A^^,7-trimethyl-7^-pyrrolo[2,3-cOpyrirnidine-6-carboxamide (276)

The synthetic route of 7781-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 50638-47-6, A common heterocyclic compound, 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, molecular formula is C7H6BrClO, 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.

Example 13i 5-(3-Bromophenyl)-5-(3-chloro-4-methoxyphenyl)-5H-pyrrolo[3,4-b]pyridin-7-amine n-Butyllithium (0.750 mL, 1.20 mmol) was added to a solution of 4-bromo-2-chloro-1-methoxybenzene (244 mg, 1.10 mmol) in THF (1.5 mL) at -78 C. under an argon atmosphere. The mixture was stirred for 5 min, then a solution of N-((3-bromophenyl)(2-cyanopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide (390 mg, 1 mmol) in THF (1.5 mL) was added. The resulting mixture was stirred at -78 C. for 15 min, then the cooling bath was removed and the mixture was stirred at rt for 1.5 h. Hydrogen chloride in methanol (3 mL, 3.75 mmol) was added and the mixture was stirred at rt for 1 h. Saturated aqueous NaHCO3 (3 mL) was added followed by DCM (3 mL). The mixture was poured into a phase separator and the organic phase was collected, concentrated and purified on a silica gel column eluted with 0-5% 0.1M NH3 in MeOH in DCM to afford 355 mg (83% yield) of the title compound: 1H NMR (500 MHz, DMSO-d6) delta ppm 8.65 (d, 1H) 8.33 (dd, 1H) 7.49 (dd, 1H) 7.41-7.47 (m, 2H) 7.29-7.36 (m, 2H) 7.22-7.29 (m, 2H) 7.06 (d, 1H) 6.90 (br. s., 2H) 3.81 (s, 3H); MS (ES+) m/z 428, 430 [M+1]+.

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; ASTRAZENECA AB; US2010/125081; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 933190-51-3,Some common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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 mixture of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (300 mg, 1.3 mmol), (S)-6-(2- methylpyrrolidin-l-yl)pyridin-2-amine (252 mg, 1.42 mmol), Pd2(dba)3 (75 mg, 0.13 mmol), BINAP (324 mg, 0.52 mmol), Cs2C03 (1272 mg, 3.9 mmol) and dioxane (20 mL) was heated to 100 C with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200 – 300 mesh, petroleum ether : ethyl acetate = 3 : 1) to give (S)-6-chloro-N-(6-(2-methylpyrrolidin-l-yl)pyridin-2-yl)imidazo [1,2- b]pyridazin-8-amine (124 mg, 29 %) as a yellow solid. LC-MS: [M+H]+, 329.0, tR = 1.95 lmin.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 203302-92-5, 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. 203302-92-5, name is 3-Bromo-2-chloro-6-fluorotoluene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Chloro-3-bromo-6-fluorotoluene (670 mg, 3 mmol), Cul (143 mg, 0.75 mmol), racemic trans-NN’-dimethylcyclohexane-1,2-diamine (213 mg, 1.5 mmol), and Nal (1.12 g, 7.5 mmol) were added to a sealed tube, degassed and dioxane (6 mL) was then added. The reaction mixture was again degassed, flushed with nitrogen and heated at 110 C. for 72 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and the solid reagents were filtered off. The filtrate was concentrated to afford a residue which was passed through a short silica gel column to provide the desired product.

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, 3-Bromo-2-chloro-6-fluorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ge, Min; He, Jiafang; Lau, Fiona Wai Yu; Liang, Gui-Bai; Lin, Songnian; Liu, Weiguo; Walsh, Shawn P.; Yang, Lihu; US2007/265332; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics