Tag: M.W=200-300

Electric Literature of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

General procedure: 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4-ethylpiperazin-l- yl)phenyl)pyrimidin-2-amine (compound of Step lh, 0.1 g) was dissolved in NMP and 2- naphthoyl chloride (42 mg, 0.220 mM) was added to the reaction mixture. The reaction mixture was stirred at RT for lh. The reaction mixture was diluted with diethyl ether, stirred for 5 min and ether was removed. The dilution of the reaction mixture with diethyl ether and removal of ether was repeated twice. The reaction mixture was further diluted with DCM and washed with aqueous saturated NaHC03. The organic layer was dried over anhydrous Na2S04, concentrated to yield crude product which was purified by flash column chromatography (silica gel, eluted with 6% MeOH in DCM) to afford the title compound ((4-(4-ethylpiperazin-l- yl)phenyl)amino)pyrimidin-4-yl)-2,3-dihydroimidazo[2, 1 -b]thiazol-6-yl)phenyl)-2-naphthamide. Yield: 0.069 g (53%); (0492) ‘H NMR (CDC13, 300 MHz): delta 8.56 (s, IH), 8.46 (s, IH), 8.19-8.17 (d, J=5.7 Hz, IH), 8.00-7.97 (m, 3H), 7.92-7.90 (d, J=6.6Hz, IH), 7.83 (s, IH), 7.62-7.58 (m, 2H), 7.50-7.47 (d, J=8.4 Hz, 2H), 7.42-7.36 (m, 3H), 6.92-6.89 (d, J=8.7 Hz, 2H), 6.74-6.72 (d, J=5.7 Hz, IH), 4.54-4.49 (t, J=6.9 Hz, 2H), 3.870-3.82 (t, J=6.9 Hz, 2H), 3.57 (m, 4H), 3.16 (m,4H), 2.54-2.52 (m, 2H), 1.17- 1.15 (t, J= 6.9Hz, 3H); MS: m/z 653.5 (M+l).The title compound was prepared in an analogous manner as the compound 1 of Example 1 involving reaction of 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4- ethylpiperazin-l-yl)phenyl)pyrimidin-2-amine (Step lh of Example 1) with 3,5-difluorobenzene- 1 -sulphonyl chloride in DCM in the presence of pyridine at RT for lh. Yield: 75.7%; (0625) 1H NMR (DMSO-d6, 300 MHz): delta 10.57 (br s,lH), 9.58 (s, IH), 9.44 (s, IH), 8.19 (d, J=5.1 Hz, IH), 7.65 (d, J=12 Hz, IH), 7.57-7.55 (d, J=5.4 Hz, IH), 7.41 (s, IH), 7.33-7.17 (m, 6H), 6.95- 6.93 (d, J=5.7 Hz, 2H), 6.40-6.38 (d, J=6 Hz, IH), 4.59-4.55 (t, J=6 Hz, 2H), 4.19-4.17 (t, J=6 Hz, 2H), 3.7 (d, J=12 Hz, 2H), 3.21-3.13 (m, 5H), 2.90-2.80 (m, 3H), 1.25 (t, J=6 Hz, 3H); m/z 672.6 (M+l).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GADEKAR, Pradip, Keshavrao; URUNKAR, Ganesh, Devidas; SEELABOYINA, Balapadmasree; DEKA, Nabajyoti; DAWANGE, Mahesh, Balasaheb; B-RAO, Chandrika; KHANNA, Smriti; WO2015/128698; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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. Computed Properties of C8H7ClF3N

Example 23 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2- pyridinyl)-4-imidazolidinecarboxamide (E23) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); A mixture of 3-methyl-2-oxo-1-(2-pyridinyl)-4-imidazolidinecarboxylic acid TFA salt (117 mg, 0.35 mmol), 1-hydroxybenzotriazole hydrate (80 mg, 0.525 mmol), 1-ethyl- 3-(3-dimethylaminopropyl)carbodiimide hydrochloride (101 mg, 0.525 mmol) and N- ethyl morpholine (0.224 ml, 1.75 mmol) in dichloromethane (8 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3- (trifluoromethyl)phenyl]methyl}amine (73.4 mg, 0.35 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for 18 hours. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic phase was separated, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 0- 10% methanol in dichloromethane to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2-pyridinyl)-4- imidazolidinecarboxamide (90 mg, 62%). LC/MS [M+H]+ = 413, retention time = 2.55 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39226-96-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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. HPLC of Formula: C6H3BrCl2

Under a nitrogen atmosphere, tert-butyllithium (1.3 Msolution in Pentane, 17.8 mL, 23.2 mmol) was added dropwise to a solution of 3,5-dichlorobenzene (5.0 g, 22.1mmol) in tetrahydrofuran (50 mL) for 30 min and the reaction was continued for 2 hours. Trifluoroacetic anhydride is then added(2.56 g, 12.2 mmol) was added dropwise to the mixed solution and stirring was continued for 2 hours while maintaining at -78 ° C. Remove the cold, gradually rose toAfter room temperature, keep the reaction at room temperature for 2.5 hours. Saturated ammonium chloride solution (50 mL) was added to terminate the reaction. The mixture was extracted with etherThe organic phase was combined and washed with saturated brine (20 mL’2). The organic phase was separated and washed with anhydrous magnesium sulfateDrying, filtration, removal of the solvent, and distillation under reduced pressure gave a colorless transparent liquid 1 (2.58 g) in a yield of 48percent.

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

Reference:
Patent; Jingmen Pharmaceutical Industry Technology Institute; Wang Yong; Li Liwei; Hu Jianmei; Gu Dongyun; Huang Daoyou; (12 pag.)CN107353189; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, 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 50638-47-6, name: 4-Bromo-2-chloro-1-methoxybenzene

Example 20 5-(3-Chloro-4-methoxyphenyl)-5-(3-(3-fluoropropoxy)phenyl)-5H-pyrrolo[3,4-b]pyridin-7-amine tert-Butyllithium (1.7 M in pentane, 0.607 mL, 1.03 mmol) was added dropwise to THF (2 mL) at -100 C. under an argon atmosphere. Then a solution of 4-bromo-2-chloro-1-methoxybenzene (137 mg, 0.62 mmol) in THF (0.5 mL) was added dropwise followed by the addition of N-((2-cyanopyridin-3-yl)(3-(3-fluoropropoxy)phenyl)methylene)-2-methylpropane-2-sulfinamide (200 mg, 0.52 mmol) in THF (2 mL). The resulting reaction mixture was left on the thawing cooling bath for 30 min and then the cooling bath was removed and the mixture was stirred at rt for 1 h. Hydrogen chloride 1.25 M in methanol (2.478 mL, 3.10 mmol) was added and the resulting mixture was stirred at rt for 1 h. The mixture was concentrated and purified by preparative HPLC. The fractions containing the product were pooled and the MeCN was removed in vacuo. Saturated aqueous NaHCO3 was added to the residue and the mixture was extracted with DCM (3*10 mL). The combined organics were passed through a phase separator and concentrated to give 75 mg (34% yield) of the title compound: 1H NMR (DMSO-d6) delta ppm 8.55-8.69 (m, 1H) 8.19-8.32 (m, 1H) 7.42-7.52 (m, 1H) 7.27-7.32 (m, 1H) 7.22-7.27 (m, 1H) 7.16-7.22 (m, 1H) 7.01-7.07 (m, 1H) 6.86-6.91 (m, 1H) 6.67-6.86 (m, 4H) 4.61 (t, 1H) 4.52 (t, 1H) 3.96 (t, 2H) 3.80 (s, 3H) 2.05-2.10 (m, 1H) 2.00-2.05 (m, 1H); MS (ES+) m/z 426, 428 [M+1]+.

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-Bromo-2-chloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US2010/125087; (2010); 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9ClO4S

-(isoindolin-2-ylsulfonyl)benzene-l,3-diol, 9 (PS2): In a 10 mL, three-necked, round-bottomed flask, 2,4-dimethoxybenzene-l-sulfonyl chloride (237 mg, 1 mmol, 1 equivalent) was dissolved in acetonitrile (3 mL) at room temperature. Triethylamine (0.3 mL) was added before isoindoline (238 mg, 2 mmol, 2 equivalent) was added. The mixture was stirred at the same temperature for 18 h and then diluted with ethyl acetate (50 mL). The mixture was washed sequentially with IN HC1 aqueous solution, saturated aqueous NaHC03, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield a solid, which was confirmed by NMR. NMR (500 MHz, CDC13) delta 7.95 (d, J=8.2 Hz, 2H), 7.29-7.25 (m, 2H), 7.22-7.20 (m, 2H), 6.55 (dd, J =8.2, 2.3 Hz, 1H), 6.44 (d, J =2.3 Hz, 1H), 4.76 (s, 4H), 3.86 (s, 3H), 3.76 (s, 3H); 13C NMR (125 MHz, CDC13) delta 164.9, 158.4, 136.9, 134.0, 127.6, 122.7, 118.8, 104.3, 99.5, 56.1, 55.9, 53.9. LRMS (ESI) calculated for [M+H]+ 320.1, found 320.0.

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHUANG, David, T.; TSO, Shih-Chia; QI, Xiangbing; GUI, Wen-Jun; WU, Cheng-Yang; CHUANG, Jacinta, L.; TAMBAR, Uttam, K.; WYNN, R., Max; WO2015/89360; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 60811-21-4,Some common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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 21 6-(3-Chloro-4-fluoro-phenyl)-4-isopropyl-3,4-dihydro-1H-quinoxalin-2-one A mixture of (3,4-dihydro-4-isopropyl-2-oxoquinoxalin-6-yl)boronic acid (2.4 g, 10 mmol), 4-bromo-2-chlorofluorobenzene (2 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml) and water (25 mol) was heated to reflux for 6 hrs. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3*). The combined organic layers were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude product (2.9 g, 91%). Recrystallization from EtOAc/hexane afforded the title compound, mp 208-213 C.: 1H-NMR (DMSO-d6) delta1.16 (d, J=6.59 Hz, 6H), 3.56 (s, 2H), 4.22 (septet, J=6.59 Hz, 1H), 6.86 (d, J=7.91 Hz, 1H), 6.96 (dd, J=7.91, 1.76 Hz, 1H), 7.01 (d, J=1.76 Hz, 1H), 7.43 (t, J=9.01 Hz, 1H), 7.61 (m, 1H), 7.82 (dd, J=7.14, 2.31 Hz, 1H), 10.47 (s, 1H). MS (EI) m/z 318 [M]++1 chlorine.

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-2-chloro-1-fluorobenzene, its application will become more common.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6380235; (2002); 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. 3386-33-2, name is 1-Chlorooctadecane, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C18H37Cl

EXAMPLE 1 Preparation of a compound of formula (I) in which R1 is a stearyl radical, R2 is a hydroxypropyl radical, n=6.3 and p=14 52.5 g (173 mmol) of stearyl chloride were added dropwise for 20 minutes at 20 C. to a solution of 12.4 g (8.3 mmol) of hydroxypropyl-beta-cyclodextrin (n=6.3), sold by the company Aldrich, in 100 ml of anhydrous pyridine. After 5 hours’ stirring at ambient temperature, the reaction mixture was poured into 400 ml of ethanol. The solid obtained was filtered off and washed three times with 200 ml portions of hot ethanol. After drying, 40.5 g of a light-beige solid which had a melting point of 39 C. were obtained. Infrared: ester band at 1745 cm-1

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 3386-33-2.

Reference:
Patent; L’Oreal; US5854225; (1998); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13745-86-3, 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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2Preparation of 11-piperazinyl-Dibenzo[B,F][1,4]Thiazepine,DihydrochlorideDimethylsulfoxide (3.0 L); piperazine (2.45 Kg); toluene (3.0 L) were charged at room temperature under nitrogen and the mixture was heated to 50 C. to 60 C.; stirred at 50 C. to 60 C. till solid dissolves and cooled to 25 C. to 30 C. To it a solution of 11-chloro-dibenzo[b,f]1,4]thiazepine (1.0 Kg) in toluene (6.0 L) was charged at 25 C. to 30 C. and stirred for 3 hours at 25 C. to 30 C. and monitored to completion. The reaction mixture was charged slowly into DI water (45 L) at 25 C. to 30 C. and stirred for 30 minutes at 25 C. to 30 C. The layers were separated at room temperature and the organic layer was washed with DI water (3×3.0 L) at room temperature. The solvent was recovered from the organic layer under vacuum at 50 C. to 55 C. to obtain oil. Ethanol (5 L) was charged into the residue and stirred to dissolve at room temperature. Concentrated hydrochloric acid (0.72 L) was added slowly at 25 C. to 30 C. and stirred until the solid precipitated. The mixture was stirred for 10 hours at 25 C. to 30 C. after precipitation, cooled to 0 C. to 5 C. and stirred for 1 hour at 0 C. to 5 C. The solid was filtered and washed with ethanol (1 L) at 0 C. to 5 C. The solid was added to pre-cooled ethanol (5 L) at 0 C. to 5 C. and stirred for 15 minutes at 0 C. to 5 C. The solid was filtered at 0 C. to 5 C. and washed with ethanol (1 L) at 0 C. to 5 C. The wet cake was unloaded at room temperature under nitrogen atmosphere and dried under vacuum at 55 C. to 60 C. until the moisture content is NMT 5.0% to obtain the title compound.Yield: 1.10 Kg

The synthetic route of 11-Chlorodibenzo[b,f][1,4]thiazepine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; US2012/71649; (2012); 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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3BrClF

EXAMPLE 65 6-(3-Chloro-4-fluoro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one Prepared from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 1-bromo-3-chloro-4-fluorobenzene according to Procedure A. White solid: mp 211-212 C.; 1H-NMR (DMSO-d6) delta10.4 (s, 1H), 7.92 (dd, 1H, J=7.13, 2.19 Hz), 7.71-7.66 (m, 1H), 7.60-7.57 (m, 2H), 7.49 (t, 1H, J=8.95 Hz), 6.96 (d, 1J=8.01 Hz), 1.67 (s, 6H); MS (EI) m/z 305 ([M +H]+, 20%); Anal. Calc. For C16H13ClFNO2: C, 62.86, H, 4.29, N, 4.58. Found: C, 62.52, H, 4.45, N, 4.42.

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; Wyeth; Ligand Pharmaceuticals, Inc.; US6444668; (2002); B1;,
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. 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Example 120 N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-5-oxo-1-(3-pyridinylmethyl)prolinamide (E120) 5-oxo-1-(3-pyridinylmethyl)proline (0.210 g, 1 mmol, prepared as described below), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.383 g, 2 mmol), and 1-hydroxybenzotriazole (0.306 g, 2 mmol) were stirred together in dichloromethane (10 ml) at room temperature for 30 minutes. The mixture was then treated with {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (0.314 g, 1.5 mmol) and the mixture was stirred overnight at room temperature. The mixture was concentrated and partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous layer was separated and extracted with more ethyl acetate and then the combined ethyl acetate fractions were washed sequentially with 3 portions of water and then with saturated aqueous sodium chloride solution. Drying over magnesium sulphate and concentration gave a solid residue which was purified by mass-directed automated HPLC to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-5-oxo-1-(3-pyridinylmethyl)prolinamide (0.031 g). LC/MS [M+H]+=412/414, retention time=1.83 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