Tag: M.W=200-300

Electric Literature of 1009102-44-6, A common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

l-(4-chlorophenyl)cyclopropanamine hydrochloride (25 mg, 0.123 mmol) was added to a stirring solution of HATU (59 mg, 0.154 mmol), DIEA (54 mu, 0.308 mmol), and 3-(2-(4-fluorophenyl)-3- (methylcarbamoyl)benzofuran-5-yl)benzoic acid (40 mg, 0.103 mmol) in DMF (1 mL) at rt. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with sat NaHC03, and sat NaCl. The organic phase was dried over Na2S04, filtered and concentrated and was purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H20/CH3CN gradient, and concentrated to give the titled compound (8 mg, 14%). 1H NMR (500 MHz, DMSO-d6) d ppm 9.37 (1 H, s), 8.46 – 8.55 (1 H, m), 8.22 (1 H, s), 7.95 – 8.05 (2 H, m), 7.86 – 7.95 (3 H, m), 7.74 – 7.83 (2 H, m), 7.59 (1 H, t, J=7.63 Hz), 7.38 – 7.44 (2 H, m), 7.30 – 7.36 (2 H, m), 7.20 – 7.28 (2 H, m), 2.86 (3 H, d, J=4.58 Hz), 1.26 – 1.36 (4 H, m). LC-MS retention time: 1.92 min; m/z (MH+): 539. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna lOu CI 8 3.0x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220nM. The elution conditions employed a flow rate of 5 ml/min , a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% MeOH / 90% H20 / 0.1% trifluoroacetic acid and solvent B was 10% H20 / 90% MeOH / 0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A = 5% CH3CN/95%H2O/0.1% TFA, Solvent B = 95% CH3CN/5% H2O/0.1% TFA, Start %B = 10, Final %B = 100, Gradient time = 15 min, Stop time = 18 min, Flow Rate = 1 ml/min. Column: Waters Sunfire C-18, 4.6 x 150 mm, 3.5 mm, Rt = 14.56 min, purity = 99%; Column: Waters Xbridge Phenyl column 4.6 x 150 mm, 3.5 mm, Rt = 13.20 min, purity = 97%.

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; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; PARCELLA, Kyle, E.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine, A.; HAN, Ying; HEWAWASAM, Piyasena; KADOW, John, F.; NICKEL, Andrew; WO2011/112191; (2011); A1;,
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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. 18112-31-7, name is 3-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

To a solution of 3-bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine (865 mg, 5.16 mmol, 1.0 equiv) in acetonitrile (15 mL) was added boronic acid (5.16 mmol, 1.0 equiv), bis(triphenylphosphine)palladium(II)dichloride (0.516 mmol, 0.1 equiv), then sodium carbonate (1.0 M aqueous solution, 10 equiv). The reaction mixture was irradiated in the microwave at 150 C. for 10 min. Purification by column chromatography gave of the product.

The synthetic route of 18112-31-7 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;,
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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. 2162-98-3, name is 1,10-Dichlorodecane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,10-Dichlorodecane

Reaction product of N,N-dimethylaminoethanol and 1 ,10-dichlorodecane (AE- DCD) [0089] N,N-dimethylaminoethanol (4.216 g, 0.047 mol) was added to a single neck round bottom flask. The flask was then fitted with a drying tube and stirred using a magnetic stirrer. 1,10-dichlorodecane (5 mL, 0.024 mol) was added slowly through a syringe to control the exothermic mixing. After completing the addition the reaction mixture was stirred under ambient conditions for 30 minutes. It was then immersed in a preheated oil bath maintained at 80 C. The contents of the flask solidified after heating for 4 h. The solid was washed with diethyl ether and dried in a vacuum oven. Yield: 6 g. 1H-NMR analysis indicated that the -CH3 group attached to the N atom shifted to 3.3 ppm after quaternization.

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 2162-98-3.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; ANBANANDAM, Parthiban; (53 pag.)WO2016/148649; (2016); A1;,
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Related Products of 179897-90-6, 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. 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 1. Preparation of 3-bromo-2-chloro-5-fluoroaniline To a sealable glass tube was charged 1,3-dibromo-2-chloro-5-fluorobenzene (12.52 g, 43.4 mmol), benzophenone imine (8.26 g, 45.6 mmol), sodium tert-butoxide (6.26 g, 65.1 mmol), and toluene (100 mL). The resulting mixture was thoroughly sparged with Argon, followed by the addition of Pd2(dba)3 (0.398 g, 0.434 mmol) and (S)-BINAP (0.81 g, 1.3 mmol), and follow by another Argon sparge. The reaction tube was sealed and heated to 85 C. in an oil bath and maintained overnight. The reaction was allowed to cool to room temperature and quenched with water (20 mL). The resulting layers were partitioned and separated. The organic phase was concentrated and assayed to be a mixture of mono- and bis-aminated products (~4:1 by HPLC area at 220 nm). The residue was dissolved in THF (70 mL), treated with aqueous 3.0 M HCl (20 mL) at room temperature for 1 hour and basified with saturated aqueous Na2CO3 solution (40 mL). The reaction mixture was allowed to partition and the layers were separated. The organic portion was separated, washed with brine, concentrated and the resulting residue was purified by flash chromatography (SiO2, 0-15% EtOAc in heptane) and 3-bromo-2-chloro-5-fluoroaniline was obtained as a light yellow solid (6.82 g, 30.4 mmol): LCMS(m/z): not ionized (MH+), tR=0.95 minute; 1H NMR (CDCl3, 300 MHz) delta 4.32 (br s, 2H), 6.44 (dd, J=9.8, 2.8 Hz, 1H), 6.77 (dd, J=7.9, 2.6 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
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Application of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

DMF (dimethylformaldehyde)To a solution of 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol)And di-tert-butylphenylamine (24.3 g, 144 mmol)And cesium carbonate (84.4 g, 239 mmol) were charged, and the mixture was heated to 140 C and reacted for 40 hours.After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 12-1].

The synthetic route of 179897-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Kim Gong-gyeom; Huh Nan-seul-a; Lee Gi-gon; Keum Su-jeong; (52 pag.)KR2018/112721; (2018); A;,
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29682-44-8, name is 1-Bromo-2,4,5-trichlorobenzene, 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. COA of Formula: C6H2BrCl3

To a sealed tube were added l -bromo-2,4,5-trichlorobenzene (3.0 g, 12 mmol), 1,2-dimethoxyethane: water ( 10 : 1 , 30 mL), (f)-2-(4-methoxystyryl)-4,4,5,5- tetramethyl- l,3,2-dioxaborolane (C6 4) (3.7 g, 14 mmol ), and potassium carbonate (3.2 g, 24 mmol) . The reaction mixture was degassed for 10 minutes with argon, followed by addition of tetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.48 mmol) . The reaction mixture was degassed for 10 minutes then heated at 90 C for 16 hours. The reaction mixture was poured in to water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated . Purification by flash column chromatography provided the title compound as an off-white solid (3.0 g, 80%) : NM R (400 MHz, CDC ) delta 7.73 (s, 1H), 7.50 – 7.45 (m, 3H), 7.20 (d, J = 16.0 Hz, 1 H), 7.02 (d, J = 16 Hz, 1H), 6.92 (d, J = 8.0 Hz, 2H), 3.84 (m, 3H) ; ESIMS m/z 313 ( [Mu + EtaGamma).

The synthetic route of 29682-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 60811-17-8, name is 5-Bromo-2-chloroaniline, 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 60811-17-8, Safety of 5-Bromo-2-chloroaniline

5-Bromo-2-chloro-phenylamine (0.48 g) is dissolved in pyridine (6 mL) and the solution is cooled to O0C. Benzenesulfonyl chloride (0.41 g) in DCM (2 mL) is added dropwise. The solution is stirred at O0C for 30 minutes and at room temperature for 2 hours. Pyridine is removed under reduced pressure and the residue is dissolved in EtOAc. The organic layer is washed with 10% aqueous HCl, saturated NaHCO3, and brine. The organic layer is dried (MgSO4), filtered and evaporated and the crude material is recrystallized from EtO Ac/heptane to afford N-(‘5-bromo-2-chloro-phenyl’)- benzenesulfonamide (O.62 g) as a solid. LCMS: Rtau = 3.06 minutes, MS: 346 (M+H).

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, 5-Bromo-2-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/81343; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 16429-44-0, 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. 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-7-chloro-1H-benzimidazole A solution of 5-bromo-3-chlorobenzene-1,2-diamine (2 g, 9.03 mmol) in formic acid (30 ml) was heated at reflux for 16 hours. The reaction progress was monitored by LCMS. Reaction mixture was concentrated under vacuum to yield brown oil. The mixture was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to yield 5-bromo-7-chloro-1H-benzo[d]imidazole as a pale yellow solid. Mass spectrum (EI, m/z): Calculated for C7H4BrClN2, 232.5 (M+H), found 233.0.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-chlorobenzene-1,2-diamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (181 pag.)US2019/47961; (2019); A1;,
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 179897-90-6 as follows. Quality Control of 1,3-Dibromo-2-chloro-5-fluorobenzene

[00185] Intermediate. 3-Bromo-2-chloro-5-fluoroaniline[00186] Step 1. 3-bromo-2-chloro-N-(diphenylmethylene)-5-fluoroaniline. A mixture of 2,6-dibromo-4-fluoro-l-chlorobenzene (865 mg, 3 mmol), benzophenone imine (0.61 ml, 3.6 mmol), Pd2(dba)3 (137 mg, 0.15 mmol), sodium t-butoxide (432 mg, 4.5 mmol), (S)-BINAP (280 mg, 0.45 mmol), and toluene (30 ml) was heated at 80 0C for 16 h. The mixture was extracted with ethyl acetate and the combined organic phase washed with brine. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by silica gel flash chromatography (40:1 to 20:1 hexanes/ethyl acetate eluant) to provide the title compound as a powder. MS m/z 388.9 (M + 1).

According to the analysis of related databases, 179897-90-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; NOVARTIS AG; HUANG, Shenlin; JIN, Xianming; LIU, Zuosheng; POON, Daniel; TELLEW, John; WAN, Yongqin; WANG, Xing; XIE, Yongping; WO2011/25927; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 320-50-3, name is 1,4-Dichloro-2-(trifluoromethyl)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 320-50-3, Safety of 1,4-Dichloro-2-(trifluoromethyl)benzene

Take 2,5-dichloro-3-trifluoromethylbenzene 6 (15.4 g) in an autoclave,Hydrazine hydrate (26g) and pyridine (150ml) were added together with ethyl acetate and methylene chloride (250ml) as organic solvents. The mixture was heated to 130C and reacted for 4 hours. After cooling, excess hydrazine was removed, vacuum distillation was performed, and the residue was added with solvent petroleum. The ether is recrystallized to give 2-chloro-3-trifluoromethylphenylhydrazine 7 (12.1 g)

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; Wei Haixia; Du Caixia; Hou Yingchang; (7 pag.)CN107915676; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics