Month: March 2021

14490-19-8, name is 1,4-Dichloropyrido[3,4-d]pyridazine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 14490-19-8

To l,4-dichloropyrido[3,4-d]pyridazine 3 (4.80 g, 24.0 mmol) and Hnig’sBase (14.7 ml, 84.0 mmol) in NMP (10 ml) was added (2R,5S)-2,5-dimethylpiperazine (4.1 1 g, 36.0 mmol). The reaction was stirred at 100C. After 2 h, the reaction contents were poured into saturated sodium bicarbonate (10x volume) and extracted with dichloromethane (4 x 50 mL). Silica gel chromatography (gradient 0 to 2.5% MeOH in 30% EtOAc in CH2Cl2 with 2.5% TEA additive) provided 1.4 g of l-chloro-4-(rac-2,5-trans-dimethylpiperazin-l-yl)pyrido[3,4- d]pyridazine 43. 1H NMR (500 MHz, CDC13) delta ppm 9.66 (s, 1 H) 9.08 (d, J=5.6 Hz, 1 H) 7.97 (d, J=5.6 Hz, 1 H) 3.77 (tdd, J=I 1.8, 5.9, 3.4 Hz, 1 H) 3.43 (dd, J=12.1, 2.6 Hz, 1 H) 3.17 – 3.32 (m, 2 H) 2.91 (dd, J= 10.5, 2.0 Hz, 1 H) 2.74 (dd, J=I 1.7, 10.3 Hz, 1 H) 1.13 (d, J=6.1 Hz, 3 H) 1.12 (d, J=6.6 Hz, 3 H).

The synthetic route of 14490-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/35568; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine

6. The 3,6-dichloro-1-methyl-1,2,4-triazolo [4,3-b]pyridazinium iodide was prepared from 3,6-dichloro-1,2,4-triazolo[4,3-b]pyridazine and methyl iodide in acetonitrile. N.m.r. in d6 DMSO: 4.38 (s, 3H); 8.45 (d, 1H); 9.12 (d, 1H).

The synthetic route of 33050-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries plc; ICI Pharma; US5049558; (1991); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 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 461432-23-5, HPLC of Formula: C15H14BrClO

50mLAdd to the three-neck bottle4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene (4.9 g, 15 mmol) and tetrahydrofuran 20 mL, stirred and cooled to -5 to 0 C,Slowly add isopropylmagnesium chloride Grignard reagent (8 mL, 2 mol/L).The system was stirred at 0 C for 2 h.In another 100mL three-neck bottle, add(2R,3R,4S,5R,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-bromotetrahydro-2H-pyran (IIc, 6.0 g, 10 mmol) ,Tetramethylethylenediamine (5wt%),Cobalt triacetylacetonate (5 wt%) and 20 mL of tetrahydrofuran,The system was cooled to 0 C.Slowly add the Grignard reagent in the previous 50mL bottle.After about 30 minutes, the addition is completed.The system is warmed to 25 to 30 C.Stir for 2h,The system was quenched with 1N aqueous hydrochloric acid.The organic phase was extracted with EtOAc, brine and evaporated.Column chromatography (PE/EA=9/1),The target product (6.0 g, yield 78%) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Fangnan Biological Technology Co., Ltd.; Zhang Nian; (6 pag.)CN104059041; (2018); B;,
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. 363-51-9, name is 2-Chloro-6-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-6-fluoroaniline

C. 2-FLUORO-4-PHENYL-6-CHLOROANILINE 2-FLUORO-6-CHLOROANILINE (28.8 g, 0.2 mol) is suspended in a solution of sodium bicarbonate (17.2 g, 0.2 mol in 150 mL water) and warmed to 60C. Elemental iodine (50.8 g, 0.2 mol) is added portionwise and the resulting mixture stirred at 60C for 3 days. After cooling to room temperature, the reaction mixture is partitioned between CH2CI2 (350 mL) and saturated sodium bisulfite solution (500 mL). The aqueous layer is re- extracted with additional CH2CI2 (250 mL) and the combined organic layers dried (MGS04) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9: 1 hexanes/EtOAc) to give 2-fluoro-4-iodo-6-chloroaniline (m. p. 85-87C). 2-Fluoro-4-iodo-6-chloroaniline (8.0 g, 36.0 MMOL) is dissolved in DMF (110 mL) and treated with 2.8 equivalents of PHENYLBORONIC acid (10.0 g, 82 MMOL), and a catalytic amount OF TETRAKISTRIPHENYLPHOSPHINE PALLADIUM (0) (3.0 g, 2.6 MMOL) as a solution in DMF (20 mL). Sodium carbonate (30 mL of 2 M aqueous solution) is added and the reaction mixture stirred and heated to 100C for 24 hours. After cooling to room temperature most of the DMF is removed by rotary evaporator under high vacuum. The residual brown oil is partitioned between ET20 (300 mL) and water (150 mL). The organic layer is washed with brine, dried (MGS04) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9: 1 hexanes/EtOAc) to give 2-fluoro-4-phenyl-6-chloroaniline (m. p. 105- 107C).

The synthetic route of 363-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/48314; (2004); 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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., Product Details of 6775-78-6

To 6-chloro-imidazo[l,2-b]pyridazine (1 eq, 17 mmol, 2.4 g) in acetic acid (10 ml) under inert atmosphere, is added dropwise bromine (1 eq, 17 mmol, 0.82 ml). After 4 hours stirring at room temperature, the reaction mixture is filtered and dried under vacuum to give 3-bromo-6- chloro-imidazo[l,2-b]pyridazine 1H nmr (MeOD) 8.42 (IH, d, J = 9.81 Hz), 8.07 (IH, s) and 7.91 (IH, d, J = 9.48 Hz).

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; NOVARTIS AG; WO2008/52734; (2008); 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. 622-86-6, name is (2-Chloroethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 622-86-6

EXAMPLE 5 Preparation of 4-(2-phenoxyethylthio)-1-B-D-ribofuranosylprazolo(3,4-d)pyrimidine Crude 2-phenoxyethyl chloride (2.7 g) was added to a stirred solution of 4-mercapto-1-B-D-ribofuranosylpyrazolo(3,4-d)pyrimidine (2.0 g) and potassium carbonate (1.07 g) in N,N-dimethylformamide. The solution was heated (40 C. on an oil bath) for 24 hours. After cooling the reaction mixture was poured into water (0.20 l) and the resultant precipitate was collected. The 4-(2-phenoxyethylthio)-1-B-D-ribofuranosylpyrazolo(3,4-d)pyrimidine so obtained was recystallised from methanol, m.p. 125-126 C.

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 622-86-6.

Reference:
Patent; Burroughs Wellcome Co.; US4299823; (1981); A;,
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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Bromo-3,5-dichlorobenzene

(l-Benzyl-lH-[l,2,4]triazol-3-yl)-(3,5-dichloro-phenyl)-amine (Compound 23) A mixture ofl-benzyl-lH-l,2,4-triazol-5-amine 2,2,2-trifluoroacetate (mixture of isomers) (292 mg, 1.01 mmol, Eq: 1.24),l-bromo-3,5-dichlorobenzene (185 mg, 819 muiotaetaomicron, Eq: 1.00), sodium tert-butoxide (341 mg, 3.55 mmol, Eq: 4.33), tris(dibenzylideneacetone)dipalladium(0) (18.7 mg, 20.5 muiotaetaomicron, eq: 0.025) and 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (34.8 mg, 81.9 muiotaetaomicron, Eq: 0.10) in a 2-5 mL microwave vessel. Sealed the vessel. Evacuated the system and recharged with nitrogen (2x). Added toluene and heated in an oil bath at 110¡ãC overnight. The reaction mixture was diluted with EtOAc, washed with water and brine. Dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF40-80 g, 25percent to 50percent EtOAc in hexanes) to give 2 major products. The more polar fraction was desired product 116 mg, which was triturated with methanol, filtered and rinsed with ether to give 42 mg (16percent) of desired product as a white solid. The less polar fraction was determined to be isomeric product, (2-Benzyl-2H-[l,2,4]triazol-3-yl)-(3,5-dichloro-phenyl)- amine. MS m/z 319 [M+H]

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 7-bromo-1-((1s,3s)-3-hydroxycyclobutyl)-1H-benzo[d]imidazole-5-carboxylic acid (2b, 100 mg, 0.321 mmol, 1 eq) and 4-[chloro(difluoro)methoxy]aniline (74.66 mg, 0.386 mmol, 1.2 eq) in DMF (2 mL) was added HATU (146.65 mg, 0.386 mmol, 1.2 eq) and DIEA (83.08 mg, 0.643 mmol, 111.97 uL, 2 eq). The mixture was stirred at 15 C. for 12 hr. LCMS showed 2b was consumed completely and desired MS was detected. The mixture was diluted with water (3 mL) and extracted with EtOAc (10 mL¡Á3). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to give 2c as a white solid. 1H NMR (400 MHz, DMSO-d6) delta10.48 (s, 1H) 8.72 (s, 1H) 8.40 (d, J=1.3 Hz, 1H) 8.05 (d, J=1.3 Hz, 1H) 7.92 (d, J=9.0 Hz, 2H) 7.36 (d, J=9.0 Hz, 2H) 5.37 (d, J=6.4 Hz, 1H) 4.96-5.08 (m, 1H) 4.01-4.13 (m, 1H) 2.89-2.98 (m, 2H) 2.36-2.43 (m, 2H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); 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. 102-49-8, name is 3,4-Dichlorobenzylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,4-Dichlorobenzylamine

A solution of 1.0 g of 2-amino-5-nitronicotinic acid and 0.96 g of carbonyldiimidazole (CDI) in 10 mL of DMF was stirred for 1 h. Then 1.0 g of 3,4-dichlorobenzylamine was added and the mixture stirred at room temperature for 1 h. The mixture was diluted with 100 mL of water. Yellow precipitate of 2-amino-N-(3,4-dichlorobenzyl)-5-nitronicotinamide was formed, which was filtered and dried under high vacuum to be used in the next step without further purification.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Koltun, Dmitry; Parkhill, Eric; Boze, Melanie; Zablocki, Jeff; Vasilevich, Natalya; Mayboroda, Elena; Glushkov, Andrei; Cole, Andrew; Chisholm, Jeffrey; US2008/255161; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1716-42-3, A common heterocyclic compound, 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, molecular formula is C9H10ClFO, 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 12 1-{1-[3-(4-Fluorophenoxy)-propyl]-piperidin-4-yl}-1H-benzimidazole To a stirred solution of 1-piperidin-4-yl-1H-benzimidazole (4.02 g) and 1-(3-chloropropoxy)-4-fluorobenzene (4.16 g) in DMF (50 ml) was added K2CO3 (4.1 g) and KI (0.2 g). The mixture was heated at 90¡ã C. for 2 h, and then allowed to cool to rt. Water (100 ml) was added and the mixture extracted with ethyl acetate (2*80 ml), and the organic layer separated and washed with water. This was further dried and concentrated in vacuo. The free base converted to the hydrochloride salt by action of HCl in ethanol. The solid was recrystallized from ethanol-diethylether to yield 4.7 g of the title compound as colourless crystals. MP. 233-235¡ã C.

The synthetic route of 1716-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/30590; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics