Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 27798-60-3, name is Methyl 2-Methoxyphenylacetate, I believe this compound will play a more active role in future production and life. 27798-60-3

(b) Sodium (590 mg) was dissolved in ethanol (45 mL) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.65 g, 12 mmol), followed by methyl 2-methoxyphenylacetate (4.7 g, 26 mmol) were added. The reaction mixture was refluxed overnight, the solvent was stripped and the residue was treated with water and then 2N HCl. The product was collected by filtration and recrystallized from ethyl acetate to afford 2.23 g of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 145-146 C.

The chemical industry reduces the impact on the environment during synthesis 27798-60-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sanofi Winthrop, Inc.; US5656629; (1997); A;,
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85920-63-4, Name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 85920-63-4, belongs to esters-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.

Acetyl-Meldrum?s acid (309 mg, 1.66 mmol) was added to a solution of the denosylated precursor from the preceding reaction (300 mg, 663 mumol) in dioxane (15 mL). The reaction was stirred for 90 min at 80 C. Then a solution of KOH in MeOH (0.1 M, 16.6 mL, 1.66 mmol) was added and stirring was continued for another 60 min at 80 C. The solvent was removed under reduced pressure and the residue separated between DCM and aqueous ammonium chloride. The aqueous phase was extracted twice with DCM and the combined organic layers were dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude product (347 mg), which yielded 16 (260, 80%) as a 1:1 mixture of diastereomers after chromatographic purification (DCM/MeOH 25/1). The diastereomers of a small sample were separated by semipreparative HPLC (ACN/H2O 70/30). Rf (DCM/MeOH 95/5): 0.45. (6aR,11aS,11bR)-N-tosyl-CPA 16a (cis-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.55 (s, 1H), 7.30-7.27 (m, 1H), 7.25 (d, J=8.2 Hz, 2H), 7.05 (d, J=7.3 Hz, 1H), 4.00 (d, J=10.9 Hz, 1H), 3.58 (dd, J=10.9, 6.0 Hz, 1H), 3.02 (dd, J=16.3, 5.8 Hz, 1H), 2.94 (dd, J=16.1, 11.7 Hz, 1H), 2.59 (Psidt, J=11.6, 5.9, 5.9 Hz, 1H), 2.49 (s, 3H), 2.36 (s, 3H), 1.67 (s, 3H), 1.58 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=194.3, 185.0, 175.4, 144.7, 135.6, 133.1, 129.8 (CH), 129.3, 128.4, 126.9 (CH), 125.5 (CH), 122.9 (CH), 120.6 (CH), 116.2, 111.6 (CH), 105.4, 70.7 (CH), 63.6, 52.4 (CH), 35.4 (CH), 26.1 (CH3), 26.1 (CH2), 24.4 (CH3), 21.5 (CH3), 19.8 (CH3); HR-ES-MS: m/z=513.1449 (calcd 513.1455 for C27H26N2NaO5S); IR: nu=3415, 1709, 1614 cm-1. (6aS,11aS,11bR)-N-Tosyl-CPA 16b (trans-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.2 Hz, 1H), 7.55 (d, J=1.7 Hz, 1H), 7.29 (Psit, J=7.8 Hz, 1H), 7.25 (d, J=8.1 Hz, 2H), 7.06 (d, J=7.3 Hz, 1H), 4.09 (d, J=10.7 Hz, 1H), 2.95 (Psidt, J=11.4, 1.7 Hz, 1H), 2.92 (dd, J=15.6, 4.6 Hz, 1H), 2.88 (dd, J=15.5, 11.8 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H), 2.32, (Psidt, J=11.8, 11.8, 4.6 Hz, 1H), 1.60 (s, 3H), 1.53 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=193.6, 185.6, 174.6, 144.7, 135.7, 133.7, 130.9 (CH), 129.9, 129.4, 126.9 (CH), 125.6 (CH), 121.3 (CH), 121.2 (CH), 118.0, 111.9 (CH), 105.3, 71.2 (CH), 62.1, 58.0 (CH), 38.4 (CH), 28.0 (CH3), 27.2 (CH2), 21.5 (CH3), 19.8 (CH3), 19.7 (CH3); HR-ES-MS: m/z=489.1497 (calcd 489.1490 for C27H25N2O5S); IR: nu=3362, 1611 cm-1.

Statistics shows that 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione is playing an increasingly important role. we look forward to future research findings about 85920-63-4.

Reference:
Article; Beyer, W.R. Christian; Woithe, Katharina; Lueke, Bettina; Schindler, Michael; Antonicek, Horst; Scherkenbeck, Juergen; Tetrahedron; vol. 67; 17; (2011); p. 3062 – 3070;,
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Adding some certain compound to certain chemical reactions, such as: 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, 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 46004-37-9. 46004-37-9

To a suspension of methyl 4-amino-2-chlorobenzoate (55.8 mmol) in EtOH (558 mL) was added silver sulfate (55.8 mmol) and iodine (58.6 mmol) under argon. The mixture was stirred for 15 min, filtered and the filtrate was concentrated in vacuo. The residue was partitioned between DCM and a 1 M aq. solution of NaOH. The organic phase was washed with a 1 M aq. solution of NaOH, dried over MgS04 and concentrated in vacuo. The crude was purified by CC (SNAP KP-SIL from Biotage) using Hept/EtOAc/MeOH from 89/11/1 to 81/19/1 to give the mixture of regioisomers as salmon solid. The mixture was enriched from 59 to 66% in methyl 4-amino-2-chloro-3-iodobenzoate by recrystallisation in Hept/EtOAc 75/25, separation of the solid methyl 4-amino-2-chloro-5-iodobenzoate by filtration and evaporation of the mother liquid. LC-MS (B): tR = 0.72 min; [M+CH3CN+H]+: 352.79 In addition, pure methyl 4-amino-2-chloro-5-iodobenzoate regioisomer was isolated as pink to orange solid. LC-MS (B): tR = 0.75 min; [M+CH3CN+H]+: 352.80

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 Methyl 4-amino-2-chlorobenzoate.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; RENNEBERG, Dorte; STAMM, Simon; WO2014/97140; (2014); A1;,
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Some common heterocyclic compound, 349-43-9, name is Ethyl 2-fluoropropionate, molecular formula is C5H9FO2, 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. 349-43-9

Syntheses of the Intermediate Sulfinamide Esters A3.3 and A3.4In a dry apparatus under an inert atmosphere a solution of diisopropylamine (3.35 g, 101 mmol) in tetrahydrofuran (25 ml) was treated with n-butyl lithium (1.6M in hexane, 20.7 ml). The solution was stirred at -7¡ã C. for 40 minutes. Thereafter, the solution was cooled to -75¡ã C. and a solution of ethyl 2-fluoropropanoate (3.98 g, 33.2 mmol) in tetrahydrofuran (5 ml) was added dropwise. After 40 minutes a solution of chlorotitanium triisopropoxide (8.64 g, 33.2 mmol) in tetrahydrofuran (15 ml) was slowly added dropwise. After 40 minutes at -72¡ã C. to the orange colored solution was added dropwise a solution of (R)-2-methyl-propane-2-sulfinic acid [1-(2-fluorophenyl)-(E)-ethylidene]-amide (intermediate A2.1) (4.0 g, 16.6 mmol) in tetrahydrofuran (5 ml). Stiffing was continued at -72¡ã C. for 4 hours, then the reaction mixture was kept at -20¡ã C. for 17 hours. For the workup, the reaction mixture was quenched with an aqueous solution of ammonium chloride (13percent, 100 ml). The precipitate formed was diluted with water and the resulting mixture extracted three times with ethyl acetate. The organic layers were washed with brine, then combined, dried and evaporated at reduced pressure. Purification of the crude product by chromatography on silica gel using a 5:2-mixture auf heptane and ethyl acetate as the eluent yielded a 1:2-mixture of the (2S,3R)-2-fluoro-3-(2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.3) and (2R,3R)-2-Fluoro-3-(2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.4) (4.43 g, 74percent) as a light yellow oil. MS (ISP): m/z=362.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 349-43-9, its application will become more common.

Reference:
Patent; Hilpert, Hans; Wostl, Wolfgang; US2012/258962; (2012); A1;,
Ester – Wikipedia,
Ester – 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 36692-49-6

Step 450b. The mixture of (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (5 g, 23.2 mmol) in acetonitrile (40 mL) was added 1,1?-carbonyldiimidazole (3.95 g, 24.5 mmol). The resulting mixture was stirred at room temperature for 20 min before being added methyl 3,4-diaminobenzoate (3.86g, 23.2 mmol). The solution was stirred at room temperature for another 3 hours before being partitioned between water and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown slurry, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow oil (8.14g, 98%). ESIMS m/z=364.17 [M+H]+. ; Step 450c. The solution of compound from step 450b in acetic acid (150 mL) was stirred at 60 C. for three days before all volatiles were removed. The resulting residue was partitioned between aqueous NaHCO3 and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown oil, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow solid (2.02 g, 28%). ESIMS m/z=346.15 [M+H]+.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Qiu, Yao-Ling; Wang, Ce; Peng, Xiaowen; Ying, Lu; Or, Yat Sun; US2020/2314; (2020); A1;,
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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 59833-69-1 as follows. 59833-69-1

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (¡Á2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (¡Á2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2065-23-8, 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. 2065-23-8, name is Methyl 2-phenoxyacetate, A new synthetic method of this compound is introduced below.

REFERENCE EXAMPLE 90 Dimethyl 2-oxo-3-phenoxy-propylphosphonate 90 STR109 Dimethyl methylphosphonate (18 ml, 0.166 mol) was addded to anhydrous THF (150 ml) under argon atmosphere and cooled to -78 C. After 20 min. a solution of n-butyl lithium in hexane (1.59N, 108.8 ml, 0.173 mmol) was added to the mixture. After being stirred for 30 min. a solution of methyl phenoxyacetate (10 ml, 0.069 mmol) in 10 ml of anhydrous THF was added, and the reaction mixture was stirred successively for 30 min. at -78 C. and for 30 min. at room temperature, and acidified with acetic acid. After confirming a weakly acidic pH of the solution thus obtained, THF was distilled out. Water (50 ml) was added to the residue, and the resulting mixture was extracted with ethyl acetate (150 ml*3). The combined organic layers were washed with 100 ml of water and with 100 ml of brine, dried over anhydrous sodium sulfate, and concentrated. The oily product was distilled under reduced pressure to afford dimethyl 2-oxo-3-phenoxypropylphosphonate (14.65 g, 0.057 mol, yield: 82.3%). B.p.: 145-147 C./0.1 mmHg. The product was identified by the following data. IR(liquid film): 3450, 3070, 3025, 2960, 2920, 2860, 1740, 1605, 1595, 1495, 1460, 1430, 1405, 1370, e1300, 1250, 1230, 1180, 1160, 1100, 1030, 890, 830, 810, 800 cm-1. NMR(90 MHz, CDCl3, delta): 3.27(2H, d, J=22.7 Hz); 3.77(6H, d, J=11.2 Hz); 4.69(2H, s); 6.84-7.38 (5H, m).

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; Toray Industries, Inc.; US4775692; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 23680-40-2 name is Methyl 3-bromopropiolate, 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. 23680-40-2

Reaction Step 2. Synthesis of 7-tert-butyl 2-ethyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylateA mixture of methyl 3-bromopropiolate (5.00 g, 28.2 mmol, 1.0 eq) and tert-butyl 1H-pyrrole-1-carboxylate (14.00 g, 84.7 mmol, 3.0 eq) in a sealed tube was heated to 90 C. for 14 h. After completion of the reaction (monitored by TLC, 5% ethyl acetate-hexane Rf=0.3), The reaction mixture was purified without work up by flash column chromatography on silica gel (100-200 mesh), eluting with 5% ethyl acetate in hexanes to afford 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate (2.0 g, 20%) as a brown oil. LCMS m/z=344.2 (M+1); purity=75%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromopropiolate, and friends who are interested can also refer to it.

Reference:
Patent; INNOV17 LLC; Gaweco, Anderson; Tilley, Jefferson; Blinn, James; US2015/252051; (2015); A1;,
Ester – Wikipedia,
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73792-08-2, These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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.

To a solution of the compound of Reference Example 11-1 (358 mg, 1.20 mmol) in dichloromethane (4 mL), oxalyl chloride (113 muL, 1.32 mmol) and DMF (5 muL) were added at 0C, and the mixture was stirred for 20 minutes. To the reaction solution, a solution of methyl 4-amino-2-fluorobenzoate (105.4 mg, 0.623 mmol) and diisopropylethylamine (310 muL, 1.80 mmol) in dichloromethane (2 mL) was added at 0C, and the mixture was stirred for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, then dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (83.2 mg, 30%). MS (ESI+) 449 (M+1, 84%)

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 73792-08-2.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; IKUMA Yohei; FUKUDA Nobuhisa; IWATA Masato; KIMURA Hidenori; SUZUKI Kuniko; EP2876105; (2015); A1;,
Ester – Wikipedia,
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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. 10602-06-9, name is Methyl 3-ethynylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 10602-06-9

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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