Month: July 2021

Electric Literature of 57310-39-1,Some common heterocyclic compound, 57310-39-1, name is 3-Bromo-4-chlorotoluene, molecular formula is C7H6BrCl, 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 7: 4-(2′-Chloro-5′-methyl-biphenyl-4-ylmethyl)-2-phenyl-morpholine; 109mg of 4-(4-Bromo-benzyl)-2-phenyl-morpholine was combined with 102mg of bis(pinacolato)diboron, 97mg of potassium acetate, l lmg tetrakis(triphenylphosphine)palladium(0), and 1.9mL DMF. The mixture was heated in a microwave reactor at 12O0C for 7 minutes and cooled. 0.8mL of 2M aqueous sodium bicarbonate was added along with lOlmg of 3-Bromo-4-chlorotoluene in 0.15mL DMF. The mixture was heated in the microwave reactor for an additional 5 minutes at 120C. The reaction was cooled and filtered through Celite, washing with methylene chloride. The eluant was concentrated and purified by flash chromatography twice using an ethyl acetate/hexanes gradient to afford 3.5mg of product. ES MS (+) m/z 378

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-chlorotoluene, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/70760; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-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.

Preparation of trans-4-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol To 6-chloro-3-bromoimidazo[1,2-b]pyridazine (1.00 g, 4.30 mmol, 1.0 equiv) and p-TSA (818 mg, 4.30 mmol, 1.0 equiv) in DMSO (7.00 mL) was added trans-4-aminocyclohexanol (1.49 g, 12.9 mmol, 3.0 equiv). The mixture was heated at 100 C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 1.1 g of the yellow solid, 83%.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 344-19-4, name is 2,6-Dichloro-4-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. Formula: C6H4Cl2FN

Preparation 10 2,6 Dichloro-4-fluoro-phenylhydrazine hydrochlorideTo a 0 0C solution of 2,6 Dichloro-4-fluorophenylamine (3.0 g, 16.6 mmol) in 12 M HCl (30 mL) and TFA (20 mL) is added slowly and dropwise NaNO2 (20 mmol, 1.37 mL) in water (6 mL). The reaction is stirred at 0 0C for 1 h. A solution of SnCl2 (5.74 g, 25.6 mmol) in 12 M HCl (16 mL) is added over 15 minutes. The ice bath is removed and the reaction is stirred for 18 h. The reaction is filtered and the solid is washed with isopropyl alcohol. The solid is dried to yield the title compound (3.0 g, 96 %). LC-ES/MS m/e 194.0 (M+ 1)

The synthetic route of 2,6-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4, Quality Control of 3-Chloro-2-chloromethyl-1-propene

General procedure: To a cooled solution (5 C) of the corresponding 4,6-O-(R)-benzylidene-d-hexopyranoside derivative (obtained using the procedure describe by our group2c) (35.4 mmol) in dry THF (70 mL) were added, successively, freshly powdered potassium hydroxide (7.0 g, 125 mmol), 18-crown-6 (0.38 g, 1.4 mmol), and 3-chloro-2-chloromethylpropene (4.1 mL, 35.4 mmol). The reaction mixture was stirred at this temperature for 3 h, and left at room temperature until all the starting material had been consumed, as monitored by TLC (5-7 days, approximately), then diluted with dichloromethane (60 mL) and washed successively with water and aqueous saturated solution of sodium bicarbonate, dried (MgSO4), filtered, and the filtrate was evaporated to dryness.

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-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vega-Perez, Jose M.; Vega-Holm, Margarita; Perinan, Ignacio; Palo-Nieto, Carlos; Iglesias-Guerra, Fernando; Tetrahedron; vol. 67; 2; (2011); p. 364 – 372;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 38762-41-3, 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 38762-41-3 as follows.

8-(4-Bromo-2-chloro-phenylamino)-imidazo[l,5-alpyridine-7- carboxylic acid methyl ester[00245] A suspension of 8-chloro-imidazo[ 1 ,5-a]pyridine-7-carboxylic acid methyl ester(300 mg, 1.43 mmol), 4-bromo-2-chloroaniline (354 mg, 1.72 mmol), Pd2dba3 (65 mg, 0.07 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (131 mg, 0.28 mmol) and K3PO4 (424 mg, 2.00 mmol) in toluene (5 ml) was degassed and then heated at HO0C for 18 hours. The reaction mixture was then cooled to room temperature and diluted with ethyl acetate. The resultant mixture was washed with water and brine, then loaded onto a 10 g Isolute SCX-2 cartridge which was eluted with methanol and then a 2M solution of ammonia in methanol. The appropriate fractions were combined and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 100%, ethyl actetate in DCM) to afford the title compound as a yellow oil (271 mg, 50%). LCMS (method B): Rx = 3.65 min, [M+H]+ = 381/383.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/85980; (2009); 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. 2163-00-0, name is 1,6-Dichlorohexane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2163-00-0

Examples 2 to 5; The procedure of Example 1 was repeated, except that the reaction of 1,6-dichlorohexane was carried out at a constant pH of 5, 6, 8 and 9. Before the start of the particular reaction, the weakly acidic mixture was adjusted to the pH of 5, 6, 8 and 9 with 2.5% sodium hydroxide solution (measurement with pH electrodes). Example 2 Example 3 Example 4 Example 5 pH value in 5.0 +/- 0.1 6.0 +/- 0.1 8.0 +/- 0.1 9.0 +/- 0.1 the reaction Residual 1,6-dichloro- <10 <10 <10 approx. 11 hexane content (ppm) Conversion of 1,6- >99.9 >99.9 >99.9 >99.9 dichlorohexane (%) In all examples (Examples 2 to 5), the resulting reaction mixture was clear and homogeneous. To determine the pure yield with respect to Examples 2 and 5, they were repeated once more. However, a GC analysis sample was not taken from the particular reaction mixture. The pure yield of the (di)sodium salt (di)hydrate of hexamethylene 1,6-bisthiosulphate was approx. 91.4%2) for the repetition of Example 2 and approx. 90.6%2) for the repetition of Example 5. 2) The pure yield for the synthesis according to Examples 2 and 5 was carried out again as in Example 1 by reacting the reaction solutions obtained in each case with aqueous NaBEC solution. In this procedure, the yield of 1,6-bis(N,N-dibenzylthiocarbamoyldithio)hexane was approx. 89.6% of theory with a content of 95% for the reaction according to Example 2 and approx. 89.7% of theory with a content of approx. 94% for that according to Example 5. Thus, the pure yield of the (di)sodium salt (di)hydrate of hexamethylene 1,6-bisthiosulphate in the inventive reaction of 1,6-dichlorohexane with sodium thiosulphate pentahydrate must have been approx. 91.4% for the reaction according to Example 2 (89.6%×0.95×1/0.931=91.4%) and approx. 90.6% for that according to Example 5 (89.7%×0.94×1/0.931=90.6%).

The synthetic route of 2163-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buding, Hartmuth; US2005/240044; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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. Safety of 3-Chloropropan-1-amine hydrochloride

Step-3: Synthesis of Compound 4 (0140) (0141) To a stirred suspension of crude (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 3 (20 g, 37.13 mmol) in MeOH (400 mL) were added 3-chloro propylamine (47 g, 743 mmol) at 0 C. and activated molecular sieves (100 g) and the reaction mixture was stirred at room temperature for 20 min. Then the reaction mixture was cooled to 0 C. and solid NaBH3CN (9.33 g, 148.5 mmol) was added to the reaction mixture and stirred at same temperature for 1 h. Then the reaction mixture was stirred at room temperature for 20 h. After removal of the molecular sieves through celite pad, the filtrate was concentrated under reduced pressure. The crude mass was dissolved in ethyl acetate (250 mL) and organic part was washed with saturated solution of NaHCO3 (100 mL), dried over Na2SO4 and concentrated under reduced pressure to get crude which was purified by column chromatography using 100-200 mesh silica gel and eluting with 8% EtOAc/hexane to afford (2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-1-(3-chloropropyl)piperidine 4 (8.0 g, 36%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6276-54-6, its application will become more common.

Reference:
Patent; CELLIX BIO PRIVATE LIMITED; Kandula, Mahesh; US9150557; (2015); B1;,
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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H6BrCl

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2×20mL) and brine (2×20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%). 1H NMR (300MHz; CDCl3): delta 7.23 (d, J 8.8Hz, 1H), 6.80 (d, J 2.9Hz, 1H), 6.71 (dd, J 3.0, 8.7Hz, 1H), 3.35-3.19 (m, 8H), 2.35 (s, 3H). MS, m/z=211 (100) [M+H]+, 213 (30).

The synthetic route of 54932-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 15205-11-5, A common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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 38 N-[(2-chloro-4-fluorophenyl)methyl]-1-(2-methyl-2-propen-1-yl)-5-oxoprolinamide (E38) Crude 1-(2-methyl-2-propen-1-yl)-5-oxoproline (~0.075 g, ~0.41 mmol, prepared as described below) was dissolved in dichloromethane (5 ml) and to this was added 1-Hydroxybenzotriazole (0.061 g, 0.45 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.068 g, 0.43 mmol), and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.087 g, 0.45 mmol). The mixture was then stirred at room temperature for 24 hrs. The mixture was diluted with more dichloromethane then washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate. The organic layer was filtered through a phase separator and evaporated to give a brown residue which was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-1-(2-methyl-2-propen-1-yl)-5-oxoprolinamide (0.018 g) as a white solid. LC/MS [M+H]+=325.1, retention time=2.40 minutes.

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; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 57310-39-1, 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 57310-39-1 as follows.

Step 1: Synthesis of 1-bromo-2-chloro-5-methyl-4-nitrobenzene (8A) A solution of compound 2-bromo-1-chloro-4-methylbenzene (50 g, 0.24 mol, 1 eq) in conc.H2SO4 (400 ml), was cooled to 0-5 C. using an ice-water-methanol bath. Fuming nitric acid (10.38 ml, 1.48 g/ml, 0.24 mol) in con.H2SO4 (26 ml) was slowly added dropwise to the mixture and then stirred at 0 C. for 3 h. The solution was poured into 500 g ice/water and extracted with dichloromethane (2*300 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated to give 58 g of 8A which was used the next step directly without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.09 (s, 1H), 7.64 (s, 1H), 2.57 (s, 3H).

According to the analysis of related databases, 57310-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; US2013/116263; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics