Tag: M.W=100-200

Synthetic Route of 2495-35-4,Some common heterocyclic compound, 2495-35-4, name is Benzyl acrylate, molecular formula is C10H10O2, 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: The catalyst precursor in form of a 0.04 M CuSO4 and 0.004 M CoCl2 solution was added to a solution of the alkene/alkyne compound in methanol. The reaction was started by adding an initial portion of NaBH4, resulting in a color change to black (in situ prepared catalyst) and vigorous gas evolution. Additional portions of NaBH4 were added in intervals of typically three or four minutes. The reaction itself was carried out at room temperature and normal atmosphere. However, generation of heat due to the exothermic character of the reaction usually heated the reaction mixture to 30-40 C. Cooling is generally not necessary in small scale. For large scale reactions a reflux condenser was used. The higher reaction temperature did not influence the reaction yield. The reaction mixture was finally quenched by adding 2 M H2SO4. Work up was carried out by extracting the water/methanol phase with DCM. The catalyst in general stays within the water/methanol layer. Drying the DCM layer with MgSO4 followed by filtration removes all remaining catalyst particles. The drying agent was filtered of and the DCM was removed in vacuo.

The synthetic route of 2495-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ficker, Mario; Svenningsen, S°ren W.; Larribeau, Thomas; Christensen, J°rn B.; Tetrahedron Letters; vol. 59; 12; (2018); p. 1125 – 1129;,
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Electric Literature of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick oil.

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-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
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A common compound: 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1559-02-0

Example 91 2″-amino-6′-(5-chloropyrid-3-yl)-l”-methyldispiro[cyclopropane-l,3′-chroman-4′,4″- imidazol]-5′(l’H)-oneStep A: A mixture of diethyl cyclopropane-l,l-dicarboxylate (14.1 mL, 80.6 mmol) and lithium tri-tert- butoxyaluminohydride (201.4 mL, 201.4 mmol) was heated to reflux in THF for 3 hours. The mixture was cooled down and partitioned between water and EtOAc. The organics were washed with water, brine and dried with Na2S04. This was concentrated down and then purified on a column using 10 to 50% EtOAc:hexanes to give ethyl l-(hydroxymethyl)cyclopropanecarboxylate (1.5 g, 10.4 mmol, 12.9%) as an 12.9%) as an oil.

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, 1559-02-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
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Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

PREPARATION 1: 1 – Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde; Step a: 4-(/ert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester:; [00160] To a 50 mL flask was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (5.0 g; 29.0 mmol), imidazole (2.37 g; 34.8 mmol), DMF (30 mL) and ter/-buryldimethylsilyl chloride (4.81 g; 32.0 mmol). The solution was stirred for 78h at 20 0C. The reaction was diluted with EtOAc (100 mL), washed with water 2 x 100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude oil was purified by flash chromatography (silica gel, hexanes/EtOAc 1:0 to 1:1) to give pure product (7.79 g, 94% yield) as a 2:1 mixture of diastereomers.1H-NMR (400 MHz, CDCl3) (J = Hz) delta mixture 4.12 (m; 2H), 3.90 (m; 0.65H), 3.58 (m; 0.35H), 2.23 (m; IH), 1.98 (m; 3H), 1.82 (m; 3H), 1.49 (m; 2H), 1.21 (m; 3H), 0.88 (s; 9H), 0.05 (s; 3H), 0.03 (s; 3H). 13C-NMR (400 MHz, CDCl3) delta mixture 175.7, 175.6, 70.5, 66.6, 60.1, 60.0, 42.2, 42.1, 34.8, 32.8, 27.2, 25.8, 25.6, 23.4, 18.2, 18.0, 14.2, -4.7, -4.9. MS (ES+) m/z 287.22 [MH+].

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
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These common heterocyclic compound, 140-11-4, name is Benzyl acetate, 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. Application In Synthesis of Benzyl acetate

General procedure: Bioreactor cultures and biotransformations using E. coli JM109(pDTG601). Growth and biotransformation in the bioreactor usingE.coli JM109 (pDTG601) were carried out using a modification ofour previously published procedure.3b Thus, 5 mL of LB mediumsupplemented with ampicillin sodium salt (0.1 g/L) and glucose(5 g/L) were inoculated with a single colony of E. coli JM109(pDTG601), and grown overnight at 37 C and 150 rpm. Two500 mL shake-flasks containing 150 mL of MSB medium wereinoculated with 1 mL of the grown culture. These precultureflasks were placed in an orbital shaker at 37 C and 150 rpm, for12 hrs. Both entire cultures were used to inoculate the bioreactor(Sartorius Biostat A plus), charged with an initial volume of 2.5 L,and set to 500 rpm, 30 C, and air flow rate of 4L/min. The pHvalue was controlled automatically to 6.8 by addition of conc.ammonium hydroxide during the whole process. A pulse ofantifoam agents (Aldrich?s Antifoam Y: Silicone dispersion inwater 1:1) was added at the beginning of the run. At 6 h afterinoculation the dissolved oxygen value sharply increased(indicating carbon deprivation), whereupon a glucose fed-batchwas started by adding glucose (0.7 g/mL solution) from an initialrate of 0.08 mL/min to 0.54 mL/min in a 20 h period. When thebiomass concentration reached 15 g/L cdw, IPTG was added toinduce toluene dioxygenase expression (IPTG final concentrationin bioreactor of 10 mg/L), and the stirrer speed was set to900 rpm. After the culture reached the stationary phase (c.a.26 h, 50 g/L cdw aprox), glucose feeding was decreased to0.25 mL/min and substrate addition was started. A solution of thecorresponding substrate in liquid paraffin (0.5 M) was added at aflow rate of 20 mL/min using a peristaltic pump. After thebiotransformation was completed, the pH of the medium in thebioreactor was adjusted to 7.5. The culture broth was centrifugedat 7000 rpm and 4 C for 30 min, the supernatant was collectedand the cell pellet properly disposed. Centrifugation led to theseparation of the liquid paraffin (which contains no detectableamounts products) from the aqueous phase. The latter wasproperly lyophilized overnight to obtain a dry powder, whichwas extracted several times with ethyl acetate until no morediols were detected by TLC. The solvent was evaporated to affordthe corresponding diol, which was washed several times withhexanes to remove the liquid paraffin traces.

The synthetic route of Benzyl acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pazos, Mariana; Martinez, Sebastian; Vila, Maria Agustina; Rodriguez, Paola; Veiga, Nicolas; Seoane, Gustavo; Carrera, Ignacio; Tetrahedron Asymmetry; vol. 26; 24; (2015); p. 1436 – 1447;,
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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. 2216-92-4, name is N-Phenylglycine Ethyl Ester, This compound has unique chemical properties. The synthetic route is as follows., Safety of N-Phenylglycine Ethyl Ester

Example 71 Synthesis of 3-(2-naphthylsulfonyl)-1-(phenyl)-imidazolidin-2,4-dione (Compound 71): In a similar manner to Example 70, 470 mg (1.28 mmol; yield: 26.6%) of the title compound were obtained as white crystals from 860 mg (4.83 mmol) of ethyl N-phenylamino-acetate and 1.39 g (81%, 4.83 mmol) of 2-naphthalenesulfonyl isocyanate. Melting point: 208-210 C. PMR (delta ppm, DMSO-d6): 4.52(s,2H), 7.1-8.3(m,11H), 8.76(s,1H).

According to the analysis of related databases, 2216-92-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suntory Limited; US5691335; (1997); A;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 5-amino-2-fluorobenzoate

A solution of 5-amino-2-fluorobenzoic acid methyl ester (340 mg, 2 mmol), 6-mercaptonicotinic acid (310 mg,2 mmol), and EEDQ (500 mg, 2 mmol) in anhydrous DMF (4 mL) was stirred overnight under N2 at room temperature,2-Bromomethylphenyl boronic acid (428 mg, 2 mmol) was added to the reaction mixture for another 16 hours at roomtemperature. The solvent was then removed by rotary evaporation, and the residue dissolved in EtOAc (25 mL), Theorganic layer was washed with H2O, 10% Na2CO3, H2O, 1 N HCl, H2O, brine, and dried over Na2SO4. The organic layerwas filtered and evaporated to yield 597 mg (68%) of the methyl ester derivative as a light yellow solid. The methyl esterintermediate (200 mg, 0.45 mmol) was dissolved in MeOH (6 mL) and 1 N NaOH (1.35 mL) was added to the reactionmixture. The reaction was stirred for 16 hours at room temperature. The MeOH was removed by rotary evaporation,and the resulting solution acidified with IN BCl. The resulting solid was washed and dried to yield 87 mg (45%) as anoff white solid. ESI-MS m/z = 426.93 [M+H]+

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; Syntrix Biosystems, Inc.; Maeda, Dean Y.; Zebala, John A.; EP2942346; (2015); A1;,
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10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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. HPLC of Formula: C9H18O4

4-Chloro-2-nitrobenzaldehyde (3.71 g, 0.02 mol) was dissolved in ethanol (40 ml).Further adding stannous chloride (18.04g, 0.08mol) and ethyl 3,3-diethoxypropionate (9.5g, 0.05mol), and reacting at 90 C for 4 hours, the reaction of the raw materials of the plate is completed; After the solvent was added, ethyl acetate was dissolved, and neutralized to a weak basic with saturated sodium carbonate; filtered, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate, and then the organic layer was combined, and then evaporated to dryness. Ethyl acetate = 10:1, then petroleum ether: ethyl acetate = 5:1) After washing, ethyl 7-chloro-3-quinolinecarboxylate (3.478 g, 74%).

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Kangrun Pharmaceutical Co., Ltd.; Jin Haowen; Xu Weiliang; Xu Weizheng; (8 pag.)CN108484497; (2018); A;,
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These common heterocyclic compound, 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, 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. Application In Synthesis of Ethyl 2-(benzyloxy)acetate

Preparation of intermediate G-1. TiCI4, Bu3N,1 -methylimidazoleA-1 G-1To a stirred solution of A-1 (60 g, 309 mmol, 1 eq) and 1 -methylimidazole (30.4 g, 370 mmol, 1 .2 eq) in CH2CI2 (1 L) was added acetyl chloride (24.3 g, 309 mmol, 1 eq) at -45 C under N2. After stirring for 20 min, TiCI4 (210 g, 1 .08 mol, 3.5 eq) and tributylamine (230 g, 1 .24 mol, 4 eq) were added to the mixture at -45C under N2, and continues to stir for 50 minutes at -45C under N2. After completion, water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over sodium sulfate. The solids were removed by filtration and the solvents of the filtrate were removed under reduced pressure. The crude was purified via silica column chromatography using a heptane to ethyl acetate gradient to afford a pale yellow oil, G-1. 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 1 .30 (t, J=7.2 Hz, 3 H), 2.28 (s, 3 H), 4.27 (q, J=7.2 Hz, 2 H), 4.41 (s, 1 H), 4.58 (d, J=1 1 .8 Hz, 1 H), 4.75 (d, J=1 1 .8 Hz, 1 H), 7.32 – 7.43 (m, 5 H)

The synthetic route of Ethyl 2-(benzyloxy)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner; JONCKERS, Tim, Hugo, Maria; LAST, Stefaan, Julien; PIETERS, Serge, Maria, Aloysius; VLACH, Jaromir; WO2012/136834; (2012); A1;,
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Reference of 18595-18-1, The chemical industry reduces the impact on the environment during synthesis 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2) [0301] Methyl 3-amino-4-methylbenzoate (A-1) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution while stirring at 0 C. The ice bath was removed and the mixture was stirred overnight. Solvents were evaporated, and the mixture was diluted with water (80 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N2O2, [M+H]+: 177. found: 177.

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-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Barr, Kenneth J.; Maclean, John K.; Zhang, Hongjun; Beresis, Richard T.; Zhang, Dongshan; Andresen, Brian M.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/191434; (2015); A1;,
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