Tag: M.W=200-300

Synthetic Route of 39149-80-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 39149-80-9 name is tert-Butyl 2-bromopropanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of tert-butyl [(li?,2No.)-l-(hydroxymethyl)-2,3-dihydro-lH-inden-2- yl]carbamate (Intermediate 6: 2.63 g, 10.0 mmol) in DCM (30 mL) was added tert-butyl- (2R/S)-bwmo propionate (2.6 g, 12.5 mmol), tetrabutylammonium hydrogen sulphate (850 mg, 2.5 mmol) and sodium hydroxide (9.6 mL, 50% w/v aqueous, 120.0 mmol) and the reaction stirred at ambient temperature for 3 h. Water (50 mL) was added and the mixture extracted with DCM (2 x 50 mL). The organic extracts were washed with water (25 mL), brine (25 mL), dried (MgSO4) and the volatiles removed under reduced pressure. The residue was purified by flash chromatography with (SiO2, wo-hexane:EtOAc, 3:1) gave the title compound (2.5 g, 64%) as an oil. 1H NMR delta (CDCl3): 1.42(m, 21Eta), 2.78(ddd, IH), 3.23(m, IH), 3.35(m, IH), 3.57(m, IH), 4.85(m, 2H), 4.14(m, IH), 4.9(m, IH), 7.17(m, 3H), 7.37(m, IH); MS m/z 414 (M+Na).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 2-bromopropanoate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82400; (2006); A1;,
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Electric Literature of 1014645-87-4, These common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, 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.

Description 156: methyl 4-(1-(5-chloro-2-(3-(3-(piperazin-1- yl)phenoxy)azetidin-1 -yl)nico inamido)cyclopropyl)benzoate (D156)A suspension of 2-(3-(3-(4-(tert-butoxycarbonyl)piperazin-1 -yl)phenoxy)azetidin-1 – yl)-5-chloronicotinic acid (D1 10) (150 mg, 0.306 mmol), 1 -Hydroxybenzotriazole hydrate (47 mg, 0.306 mmol) and 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (88 mg, 0.46 mmol) in dimethylformamide (2ml) was stirred 40 min at room temperature. A solution of methyl 4-(1 -aminocyclopropyl)benzoate (D7) (68.9 mg, 0.306 mmol) and triethylamine (0.042ml, 0.306 mmol) in dimethylformamide (2ml) was added and the resulting mixture was stirred 40 min at room temperature. Water (2ml) was added and the resulting precipitate was collected by filtration and purified by Biotage column (1 Og) eluting with a mixture dichloromethane/ethylacetate from 100 /0 to 80/20. Collected fractions, after solvent evaporation, afforded tert-butyl 4-(3-((1 -(5-chloro-3-((1 -(4- (methoxycarbonyl)phenyl)cyclopropyl)carbamoyl)pyridin-2-yl)azetidin-3- yl)oxy)phenyl)piperazine-1 -carboxylate (135 mg)MS: (ES/+) m/z: 662.5 [MH+] C35H40CIN5O6 requires 661 .271 H NMR (400MHz ,DMSO-d6) delta = 9.25 (s, 1 H), 8.23 (d, J = 2.4 Hz, 1 H), 7.85 (d, J = 8.3 Hz, 2 H), 7.79 (d, J = 2.4 Hz, 1 H), 7.33 (d, J = 8.8 Hz, 2 H), 7.13 (t, J = 8.3 Hz, 1 H), 6.59 (d, J = 7.8 Hz, 1 H), 6.38 (s, 1 H), 6.20 (d, J = 5.9 Hz, 1 H), 5.04 (br. s., 1 H), 4.32 (dd, J = 6.4, 9.8 Hz, 2 H), 3.86 (s, 3 H), 3.80 (dd, J = 3.7, 10.0 Hz, 2 H), 3.43 (d, J = 4.9 Hz, 4 H), 3.14 – 3.04 (m, 4 H), 1 .42 (s, 9 H), 1 .33 (d, J = 2.9 Hz, 4 H)

Statistics shows that Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride is playing an increasingly important role. we look forward to future research findings about 1014645-87-4.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
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Related Products of 1000342-11-9, 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) Methyl 5 -bro -2-methyl-3 -((tetrahydro-2H-pyran-4-yl)amino)benzoate A I L round-bottomed flask was charged with methyl 3-amino-5-bromo-2- methylbenzoate (15.26 g, 62.5 mmol) and dihydro-2H-pyran-4(3H)-one (9.39 g, 94 mmol) in 1 ,2-dichloroethane (DCE) (250 mL) to give a yellow solution at room temperature under nitrogen. Acetic acid (21.47 mL, 375 mmol) was added to the reaction mixture. After 30 min, sodium triacetoxyborohydride (39.8 g, 188 mmol) was added to the reaction mixture. After 3 h, sodium triacetoxyborohydride (39.8 g, 188 mmol) was added to the reaction mixture. The reaction was stirred overnight, at which time it was diluted with water and neutralized with NaHC03 to pH 7. The reaction mixture was extracted with EtOAc (3x). The combined EtOAc layers were stirred with Na2S04 and activated carbon darco for 30 min, then filtered through a pad of Si02 (2″ x 1″) and concentrated. The solids were stirred with ether and filtered to obtain methyl 5-bromo-2-methyl-3- ((tetrahydro-2H-pyran-4-yl)amino)benzoate (15.4 g, 46.9 mmol, 75 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 6.98 (d, J=2.02 Hz, 1 H), 6.94 (d, J=1.77 Hz, 1 H), 5.03 (d, J=8.08 Hz, 1 H), 3.94 – 3.84 (m, 2 H), 3.80 (s, 3 H), 3.64 – 3.51 (m, 1 H), 3.44 (td, J=11.68, 1.89 Hz, 2 H) 2.15 (s, 3 H), 1.84 (dd, J=12.63, 2.02 Hz, 2 H), 1.43 – 1.69 (m, 2 H). MS(ES) [M+H]+ 328, 330.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; DONATELLI, Carla, A.; WO2014/107277; (2014); A1;,
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Electric Literature of 53518-15-3,Some common heterocyclic compound, 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, molecular formula is C10H6F3NO2, 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.

A vial was charged with S21 (60 mg, 0.117 mmol), oxalyl chloride (12 iiL, 0.141 mmol, 1.2 eq.) and DCM (1.00 mL) and the content was stirred at room temperature and ambient atmosphere for 30 minutcs. 7-amino-4-(trifluoromethyl) coumarin (81 mg, 0.352 mmol, 3 eq.) and DIEA (126 .tL, 0.704 mmol, 6 eq.) were then added and the contents were stirred for lh, after which the solvent was concentrated to dryness, and the crude product was purified by silica gel chromatography (0-30% EtOAc/DCM, linear gradient) to afford S7 (53 trig, 62%).?H NMR (CDC13, 400 MHz) 5 8.09-7.95 (m, 2H), 7.78 (m, 1H), 7.60 (td, J= 4.6, 2.2 Hz, 1H), 7.54 (if, J 5.6, 1.1 Hz, 1H),7.45 (m, 1H), 6.86 (d, J- 2.6 Hz, 1H), 6.76 (ddd, J 8.8, 3.7, 1.2 Hz, 2H), 6.62 (d, J 2.8 Hz, 1H), 6.60 (s, 1H), 6.42 (dd, J= 8.9, 2.7 Hz, 1H), 6.24 (dd, J- 8.8, 2.6 Hz, 1H), 3.88 (t, J 7.2 Hz, 4H), 3.81 (s, 3H), 3.65 (t, J= 6.2 Hz, 2H), 3.31 (t, J 6.6 Hz, 2H), 2.35 (p, J 7.2 Hz, 2H), 2.06 (p, J= 6.3 Hz, 2H), 0.71 (s, 3H), 0.59 (s, 3H).

The synthetic route of 53518-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HOWARD HUGHES MEDICAL INSTITUTE; LAVIS, Luke; JRADI, Fadi, M.; (109 pag.)WO2018/182811; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55666-42-7,Some common heterocyclic compound, 55666-42-7, name is tert-Butyl 2-bromobenzoate, molecular formula is C11H13BrO2, 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.

The crude intermediate (2b) (109.6 g, 426 mmol) and 3-fluoro-4-methylphenyl-boronicacid (72.2 g, 449 mmol) were suspended in isopropyl alcohol (360 mL, 4.7 mmol). A 2.0M solution of sodium carbonate in water (360 mL, 720 mmol) was added and the mixture was degassed under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (4.9 g, 4.3 mmol) was then added and the mixture was stirred at 90 C. for 46 hours. The mixture was cooled to room temperature, diluted with EtOAc (800 mL), and the layers were separated. The organic was washed with saturated aqueous NaCl and concentrated under reduced pressure. The recovered oil was purified by silica gel chromatography (3×4-6% EtOAc :hexanes) to yield intermediate (2c) as a clear oil (93.3 g).

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

Reference:
Patent; Zhang, Weijiang; Colson, Pierre-Jean; Fass, Gene Timothy; US2011/77411; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 57267-03-5, A common heterocyclic compound, 57267-03-5, name is Ethyl 2,2,2-triethoxyacetate, molecular formula is C10H20O5, 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.

2,5-Diamino-benzene-1 ,4-dithiol hydrochloride (5.00 g; 20.39 mmol; 1.00 eq.) is suspended in anhydrous N,N-dimethylformamide (37 cm3) at 50 C. Anhydrous pyridine (3.39 g; 3.49 cm3 42.82 mmol; 2.10 eq.) is slowly added and the mixture stirred at 50 00 for 1 hour under a flow of nitrogen. The clear yellow solution obtained is transferred to a flask containing triethoxy-acetic acid ethyl ester (16.62 g; 75.45 mmol; 3.70 eq.) andyttrium(III) triflate (0.57 g; 1 .02 mmol; 0.05 eq.). Slow precipitation is observed. The mixture is stirred at 60 00 for 72 hours under nitrogen. Subsequently, the mixture is cooled to room temperature. The precipitate is isolated by filtration and washed copiously with methanol, yielding the product as a yellow powder (4.07 g, 59.3%).1H NMR (300 MHz, Chloroform-d) 6: 8.84 (5, 2H), 4.60 (q, 4h), 1.52 (t,6H).

The synthetic route of 57267-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; NANSON, Lana; PRON, Agnieszka; KROMPIEC, Michal; (147 pag.)WO2017/157782; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, belongs to esters-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 82702-31-6, Application In Synthesis of Methyl 3-bromo-4-fluorobenzoate

Methyl 3 -bromo-4-fluorobenzoate (699 mg, 3.00 mmol), 1 -(4-hydroxy-3 , 5- dimethylphenyl)ethanone (493 mg, 3.00 mmol), and cesium carbonate (1.47 g, 4.50 mmol) were combined in dimethyl sulfoxide (3 mL). The reaction mixture was heated at 100 C for 16 hours, cooled to ambient temperature, and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydroussodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 10-20 % ethyl acetate in heptanes) to provide the title compound (540 mg, 48 %).

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, Methyl 3-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1150566-27-0, 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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (500.0 mg, 2.21 mmol) in dioxane:EtOH:H2O (4:1:3, 9 mL), (3,5-dimethylisoxazol-4-yl)boronic acid (404 mg, 2.87 mmol), Cs2CO3 (1.45 g, 4.42 mmol) and Pd(PPh3)4 (127.0 mg, 0.11 mmol) were added and the reaction was refluxed for 15 h. After cooling to room temp, the solvents were evaporated and the solid was taken up in THF (6 mL). A solution of LiOH (106.0 mg, 4.42 mmol) in 0 (3 mL) was added, the mixture was stirred for 15 h. The solvent was removed under reduced pressure and the residue was acidified to pH 4 with 3N HCl. The volatiles were evaporated under reduced pressure and the solid was triturated with MuepsilonOmicronEta:0 (1:1). Upon filtration 6-(3,5-dimethylisoxazol-4-yl)imidazo[1,2-b]pyridazine-3-carboxylic acid was obtained (331.0 mg, 58%). MS (ESI) calcd for C12H10N4O3: 258.1; found: 258.9 [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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Ester – Wikipedia,
Ester – 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 52787-14-1 as follows. COA of Formula: C11H12O4

To a mixture of K2CO3 (1194.5 g), homoterephthalic acid dimethyl ester (600 g) in DMAc (3000 mL), propargyl bromide (582.43 g) was added followed by TBAI (106.41 g) at 25-30 C. and stirred for 20-26 hours. The reaction was monitored by HPLC and found the ratio of Monopropargyl homoterephthalic Acid Dimethyl Ester to that of dipropargyl homoterephthalic Acid Dimethyl Ester to be not less than 85:15. After 26 hours the reaction mixture was quenched with DM water (3000 ml) and extracted with ethyl acetate (2*3000 ml). The organic layer was separated and back-extracted with DM water (3000 ml). The organic layer was then evaporated to dryness at reduced pressure on a rotary evaporator (below 60 C.). Further IPA (1000 ml) was added to the residue and evaporated to dryness at reduced pressure. The crude product was crystallized by dissolving in IPA (000 ml) at 45-50 C. and cooled to 0-5 C. and stirred for 1-2 hours. The product was vacuum filtered. The product obtained was further crystallized with IPA (1800 ml) saturated with Ethyl acetate (54 ml) by dissolving at 55-60 C. and stirred at 20-25 C. for 2-3 hours, followed by stirring at 0-5 C. for 2-3 hours. The solid was filtered and dried under vacuum at 40-45 C. to give 466 g (65.6%) of the title compound. Purity: 99.19%

According to the analysis of related databases, 52787-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fresenius Kabi Oncology Limited; Lahiri, Saswata; Gupta, Nitin; Singh, Hemant Kumar; Panda, Nilendu; Handa, Vishal; Abul, Azim; Gupta, Chandan Kumar; Sanghani, Sunil; Sonavane, Ghanashyam Madhukar; US2015/183789; (2015); A1;,
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Ester – an overview | ScienceDirect Topics

Related Products of 14062-25-0, 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 14A Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate 1.45 g (36.2 mmol) of sodium hydride in mineral oil (60% pure) were initially charged in 100 ml of DMF. A mixture of 4.0 g (16.5 mmol) of ethyl (4-bromophenyl)acetate and 6.5 g (34.6 mmol) of 1,2-dibromoethane was dissolved in 50 ml of THF and slowly added dropwise. The mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 mum, 250 mm*40 mm (30% methanol/70% water to 100% methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.15 g (26% of theory) of a liquid. GC-MS [Method 5]: Rt=5.45 min; MS(ESIpos): m/z=268/270 (M+) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.09 (t, 3H), 1.16-1.20 (m, 2H), 1.46-1.50 (m, 2H), 4.02 (q, 2H), 7.26-7.31 (m, 2H), 7.47-7.51 (m, 2H)

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, Ethyl 2-(4-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); A1;,
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Ester – an overview | ScienceDirect Topics