Tag: M.W=100-200

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

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

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

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 452-83-5 as follows. Safety of 2-Chloro-5-fluoroaniline

Example 1; Preparation of 6-methoxy-8-[4-(l-(5-fluoro)-qumolin-8-yl-piperidin-4-yI)-piperazin-l- ylj-quinoine (Form A)Step 1: 5-Fluoro-8 chloroquinolineTo a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and wi-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 mL of 70 % sulfuric acid dropwise. The reaction temperature was raised to 140 C for 2 h. The mixture was then cooled, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and extracted with CH2CI2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP = 74-76C; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

According to the analysis of related databases, 452-83-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; WO2007/146116; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. Safety of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

The synthetic route of 918538-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, 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 3972-56-3, category: chlorides-buliding-blocks

General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with NaH (60.0 mg, 60percent,1.2 mmol) and o-xylene (1 mL), and then phenol (1.2 mmol) wasadded. After stirring for 15 min, aryl halide (1.0 mmol) and the solution of Pd(dba)2 (11.5 mg, 0.02 mmol) and L1 (13.7 mg, 0.03 mmol) in o-xylene (1.5 mL) were added sequentially. The septum was replaced with an inside reflux condenser, and then the reaction mixture was stirred for 18 h at 110 C. Then, reaction mixture was cooled to room temperature and quenched with saturated NH4Cl(5 mL). After separating the organic phase, the aqueous phase was extracted with diethyl ether (3 mL3), and the combined organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and then the crude material was purified by column chromatography on silica gel.

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Reference:
Article; Zhang, Yi; Ni, Gang; Li, Chengjun; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 71; 30; (2015); p. 4927 – 4932;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4152-90-3, 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 4152-90-3 as follows.

To compound 2 (3 g, 9.2 mmol) at room temperatureEthanol (50mL)Et3N (2.6 mL, 18.4 mmol) was added to the solution.And 3-chlorobenzylamine (2.1 mL, 18.4 mmol),The resulting mixture was stirred at 40 ¡ã C for 5 h;Concentrated and the residue is purified by silica gel column(by volume ratio, DCM: MeOH: NH3¡¤H2O=200:10:0.1),Obtaining colorless oily compound 3(3.13g, 82percent),

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Bio-technology Institute; The Chinese People’s Liberation Army Military Academy Of Sciences Military Medical Institute; Liu Mingliang; Lv Kai; Zhong Wu; Cao Ruiyuan; Wang Apeng; Yan Yunzheng; Tao Zeyu; He Qinghao; Wang Hongjian; Li Wei; Geng Yunhe; (29 pag.)CN108892693; (2018); A;,
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. 57946-56-2, name is 4-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-2-fluoroaniline

EXAMPLE 5 Preparation of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide A solution of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extract is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a purple oil. Flash column chromatography of the oil using silica gel and 15 to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, 69% yield, mp 81-82 C.) which is identified by 1H, 13C and 19F NMR spectral analyses.

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

Reference:
Patent; American Cyanamid Co.; US6303783; (2001); B1;,
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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C2Cl2N4

Example 1 General Phase-Transfer Protocol for Tetrazine Insertion A 50 mL glass vial, was charged with unprotected peptide 1 (20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH ?5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) to yield an orange powder after lyophilization. A 50 mL glass vial, was charged with unprotected peptide 1a (11.4 mg, 20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH 5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) (gradient 5-15% organic over 5 min) to yield 10.1 mg of 2a (78%) an orange powder after lyophilization. 1H NMR (500 MHz, D2O) delta ppm 1.36 (quin, J=7.80 Hz, 2H) 1.58-1.66 (m, 3H) 1.68 (q, J=7.90 Hz, 2H) 1.79 (ddd, J=13.90, 8.30, 5.50 Hz, 1H) 1.78 (ddd, J=13.25, 8.10, 5.30 Hz, 1H) 2.07 (q, J=7.34 Hz, 2H) 2.39 (dd, J=7.30, 5.10 Hz, 1H) 2.39 (dd, J=9.80, 7.40 Hz, 1H) 2.93 (t, J=7.48 Hz, 9H) 3.50 (dd, J=15.60, 4.06 Hz, 3H) 3.54 (dd, J=18.20, 6.20 Hz, 1H) 3.57 (dd, J=11.30, 7.70 Hz, 1H) 4.10 (t, J=6.52 Hz, 1H) 4.14 (dd, J=8.44, 5.24 Hz, 1H) 4.20 (dd, J=7.10, 6.40 Hz, 1H) 4.53 (dd, J=15.39, 2.99 Hz, 1H) 4.56 (dd, J=15.60, 4.92 Hz, 1H) 4.80 (t, J=3.42 Hz, 1H) 4.99 (dd, J=4.90, 1.90 Hz, 1H). 13C NMR (126 MHz, D2O) delta 178.6, 178.1, 171.7, 170.6, 170.5, 169.9, 169.1, 169.1, 61.8, 55.0, 53.9, 52.4, 52.3, 51.5, 39.1, 31.4, 31.1, 30.7, 30.2, 26.7, 26.2, 22.1. HRMS (ES) found m/z 647.2026 [(M+H)+. calcd for C22H35N10O9S2: 647.2024].

According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Trustees Of The University Of Pennsylvania; Smith, III, Amos B.; Brown, Stephen; (18 pag.)US2015/376579; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 870-24-6,Some common heterocyclic compound, 870-24-6, name is 2-Chloroethanamine hydrochloride, molecular formula is C2H7Cl2N, 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 I: 2-(2-Methyl-1H-pyrrol-1-yl)ethanamine Sodium hydroxide anhydrous (9.87 g, 0.246 mol, 4.0 eq.) and TBAHS (0.838 g, 0.002 mol, 0.04 eq.) were added to a solution of 2-methyl-1H-pyrrole (5.0 g, 0.061 mol, 1.0 eq.) in acetonitrile (180 ml) at 0 C. and the mixture was stirred at RT for 1 h. 2-Chloroethylamine hydrochloride (8.59 g, 0.074 mol, 1.2 eq.) was added to the reaction mixture and it was then heated at reflux for 16 h. The reaction mixture was cooled to RT, filtered through celite and washed with 10% MeOH/DCM (200 ml). The filtrate was concentrated under reduced pressure to give the crude product which was used in the next step without further purification. Yield: 100%, crude (7.6 g, 0.061 mol)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloroethanamine hydrochloride, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; US2012/58999; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics