Author: Jessica.F

These common heterocyclic compound, 5338-44-3, name is Ethyl 4-acetamidobenzoate, 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. Computed Properties of C11H13NO3

General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C.

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

Reference:
Article; Baykov, Sergey; Sharonova, Tatyana; Shetnev, Anton; Rozhkov, Sergey; Kalinin, Stanislav; Smirnov, Alexey V.; Tetrahedron; vol. 73; 7; (2017); p. 945 – 951;,
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Electric Literature of 201162-53-0, These common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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.

Aldehyde Intermediate 2 (1.0 equiv) and /er/-butyl 3,8-diazabicyclo[3.2. l]octane-3- carboxylate (1.2 equiv) were combined into l,2-DCE (5 mL). To the mixture was added acetic acid (0.5 equiv). The mixture was stirred at rt for 3h. Solid NaBH(OAc)3(3.0 equiv) was then added into the reaction. The resulting mixture was stirred at rt overnight. The reaction was quenched with MeOH (10 mL) and washed with saturated NaHC03, water, and brine. The crude mixture was purified on a silica gel column to afford /er/-butyl 8-((2-ethyl-4′-(l,l,l,3,3,3-hexafluoro-2- hydroxypropan-2-yl)-[l,r-biphenyl]-4-yl)methyl)-3,8-diazabicyclo[3.2. l]octane-3-carboxylate (yield 55%) as a white solid.

The synthetic route of 201162-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ESCALIER BIOSCIENCES B.V.; MOHAN, Raju; NUSS, John; HARRIS, Jason; YUAN, Shendong; (144 pag.)WO2019/177996; (2019); A1;,
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Application of 22958-64-1, 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. 22958-64-1, name is 2-(4-Sulfamoylphenyl)acetic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00324] To a solution of 2-amino-5-(cyclohexylmethyl)-6,6-dimethyl-4, 5,6,7- tetrahydrothieno[3,2-c]pyridine-3-carbonitrile Core-1 c_A (1.15 g, 3.8 mmol) in DMF (12 mL) was added 2-(4-sulfamoylphenyl)acetic acid (1.23 g, 5.7 mmol), DIPEA (982 mg, 7.6 mmol) and a solution of T3P in EtOAc (4.84 g, 50% w/w, 7.6 mmol). The mixture was stirred at 65 C for 1 h. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (15 mLx4). The organic layer was concentrated. The residue was purified by column chromatography on silica (PE:EtOAc=10:1 ~2:1) to afford the desired product (1.15 g, yield 60%) as light yellow solid; LC-MS Rt 1.08 min, MS m/z [M+H]+ 501.3; Method 1 ; 1H NMR (400 MHz, DMSO-cfe) d 1 1.9 (s, 1H), 7.78 (d, J = 8.4 Hz, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.33 (s, 2H), 3.96 (s, 2H), 3.49 (s, 2H), 2.46 (s, 2H), 2.24 (d, J = 6.8 Hz, 2H), 1.76 – 1.73 (m, 2H), 1.67 – 1.64 (m, 3H), 1.39 – 1.33 (m, 1H), 1.25 – 1.15 (m, 3H), 1.02 (s, 6H), 0.88 – 0.75 (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, 2-(4-Sulfamoylphenyl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); A1;,
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Application of 115643-59-9, These common heterocyclic compound, 115643-59-9, name is 2-Amino-6-fluorobenzamide, 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.

Step 1 To a solution of 2-amino-6-fluorobenzamide (3.80 g, 24.7 mmol) and triethylamine (2.99 g, 29.6 mmol) in THF (50 mL) was added dropwise ethyl chloroglyoxylate (3.70 g, 27.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was suspended in EtOH, and insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate as a white powder (4.95 g, 79%).

Statistics shows that 2-Amino-6-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 115643-59-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
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Electric Literature of 132289-57-7, 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. 132289-57-7, name is N,2-Dimethoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the above amide (260mg) in THF (5ml) at-78 C was added a solution of 2-thienyllithium (1 M in THF, 2. 15ml). The solution was stirred for 2hr at-78 C and warmed to-20 C for an additional 2hr. The reaction was quenched with saturated ammonium chloride and extracted with CH2CI2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 250mg of product (82%).

The chemical industry reduces the impact on the environment during synthesis N,2-Dimethoxy-N-methylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/68460; (2005); A1;,
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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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl methylcarbamate

2-Bromo-5-hydroxy-6-nitropyridine (132.8 g, 0.606 mol), cesium carbonate (594.7 g,1.83 mol), tert-butyl methylcarbamate (116.7 g, 0.890 mol) and anhydrous DMF (4.0 L) were combined and the resultant orange mixture was sparged with nitrogen for 10 minutes. Xantphos (53.1 g, 0.0918 mol) and palladium acetate (13.5 g, 0.0601 mol) were then added and the solution was heated to 80C with continuous nitrogen gas sparging for 3 days. The mixture was allowed to cool and stir overnight. 2-Methyltetrahydrofuran (MeTHF, 4.OL) wasadded and the resultant slurry was stirred for 2.5 hours and then filtered through Celite. Thefilter cake was washed with 2 x 1.0 L of MeTHF. The filtrate was then partitioned with 8.0 Lof water. The organic layer was discarded and the aqueous layer acidified to pH 1-2 with 60mL of 12N HC1. Ethyl acetate (4.0 L) was added and the layers were separated. The organic layer was washed with water (2.0 L). The aqueous layer was back extracted with EtOAc (2 x2.0 L). The combined organic extracts were concentrated on a rotary evaporator to a brown oil. The residue was twice dissolved in EtOAc (1.0 L each time) and concentrated again. The brown oil was then dissolved in MTBE (300 mL) and loaded onto a silica gel column (SiliaFlash G-60, 3.0 L, 1.5 kg) that was pre-conditioned with 10% EtOAc/n-heptane. Thecolumn was then eluted sequentially with 10%, 20% and 30% EtOAc in n-heptane. The fractions were discarded until the eluate was yellow and then collected until cessation of color. Concentration of the combined yellow fractions on a rotary evaporator yields two crops of tert-butyl [5-hydroxy-6-nitro-2-pyridinylj(methyl)carbamate of 61.5 g and 21.3 g, (respective LC purities = 98.7% and 97.0%) with a combined yield of 82.8g (51%).

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; NAVIDEA BIOPHARMACEUTICALS, INC.; CESATI, Richard R., III; CASEBIER, David S.; MORETON, Richard Christian; (49 pag.)WO2017/87965; (2017); 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. 147962-41-2, name is N-Propylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H10N2O2S

The compound of Example 1 (10 g; 20.6 mmol), propylsulfamide (3.1 g; 22.6 mmol; 1.1 eq.; prepared as described in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861), TBAF.3H20 (19.5 g; 61.7 mmol; 3 eq.) and potassium carbonate (8.5 g; 61.7 mmol; 3 eq.) were suspended in DMSO (100 mL). The mixture was heated to 100C for 1 h and then cooled to 20-25C. Water (100 mL) and DCM (100 mL) were added. The org. layer was washed 3 times with water (100 mL each time), 20% aq. citric acid (100 mL) and water (100 mL) before being concentrated under reduced pressure to dryness. The residue was suspended in EA (15 mL) and heated to reflux. Hept (30 mL) was added. The mixture was allowed to cool to 20-25C on its own. The precipitate was filtered off and rinsed with Hept (10 mL). The beige solid thus collected (11.0 g) was recrystallized from EA (30 mL) and Hept (25 mL) to afford the title compound as a white solid (6.4 g; 53% yield). (0323) The product had MS and NMR data equivalent to those reported in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861. LC-MS (method 1): tR = 1.89 min; 100% a/a.

According to the analysis of related databases, 147962-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; ABELE, Stefan; FUNEL, Jacques-Alexis; SCHINDELHOLZ, Ivan; WO2015/121397; (2015); A1;,
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Synthetic Route of 147291-66-5, A common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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.

The solution of EDCI (3.14g, 16.38mmol) and DMAP (100mg, 0.82mmol) in 10mL DCM was added dropwise to a mixture of tert-butyl-3-aminobenzyl-carbamate (2.0g, 9.01mmol) and benzoic acid (1.0g, 8.19mmol) in 20mL DCM at 0C under nitrogen atmosphere, and the mixture was warmed to r.t. and stirred overnight. After quenched with water and extracted with DCM, the organic layer was washed with 1M NaOH (20mL), 1M HCl (20mL), and saturated NaHCO3 (10mL), dried over Na2SO4, and concentrated under reduced pressure. The Boc-protected 12a was dissolved in DCM (5mL), trifluoroacetic acid (5mL) was added. The reaction mixture was allowed to stir for 2hat r.t. and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel and further purified by recrystallization (ethyl ether) to obtain the title compound as a white solid (1.2g, yield 64.8%). 1H NMR (600MHz, DMSO-d6) delta: 10.42 (1H, s), 8.34 (3H, s), 8.01-7.96 (3H, m), 7.70 (1H, d, J=8.4Hz), 7.61 (1H, t, J=8.4Hz), 7.54 (2H, t, J=7.8Hz), 7.41 (1H, t, J=7.8Hz), 7.22 (1H, d, J=7.8Hz), 4.04 (2H, s). 13C NMR (150MHz, DMSO-d6) delta: 166.1, 139.9, 135.2, 134.9, 132.1, 129.4, 128.8, 128.1, 124.4, 121.3, 121.0, 42.9.

The synthetic route of 147291-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Yaxue; Wang, Zhongli; Zhang, Jianchen; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 178 – 184;,
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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 20348-09-8 as follows. Safety of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

a) 3,4-Dihydro-2H-pyrido[3,2-&][l,4]oxazine; To an ice-cold solution of 4H-rhoyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TetaF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TetaF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H2O (4 mL) followed by NaOH (4 mL, 15%) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85%) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) delta 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e 31 (M + eta)

According to the analysis of related databases, 20348-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
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Synthetic Route of 6292-59-7, These common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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.

General procedure: To a solution of substituted acetophenone (72.4mmol) 10 in CH3CN (100mL), Br2 (11.57 g, 72.4 mmol) in CH3CN (20 mL) was addeddropwise. The reaction was stirred at room temperature overnight. Solvent wasconcentrated in vacuum and the residue was diluted with ethyl acetate (150 mL)and washed with brine. The organic layer was dried over anhydrous Na2SO4and evaporated. The resulting solid was triturated with cyclohexane (50 mL) andfiltrated to give alpha-bromoacetophenone 11as a white solid. The aqueous solution of NaN3 (4.71 g, 72 mmol) wasadded to the solution of 11 (60mmol) in CH3OH (80 mL) with stirring and cooling. After 4 h, 200 mLwater was added and a large amout of white precipitate was formed. Compound 12 was obtained by filtration. A mixture of 12 (26.3 mmol), hydrochloric acid (7.98 g, 78.8 mmol) and thecatalytic amount of Pd/C was stirred at room temperature under H2 (1atm) overnight. Solvent was separated from Pd/C by filtration through Celite.The solvent was removed and the resulting residue was triturated with ethylacetate (10 mL) and filtrated to give compound 13. A mixture of 14(29.1 mmol), EDCl (7.5 g, 39.67 mmol), HOBT (5.5 g, 39.67 mmol)and N-methylmorpholine (10.5 g, 105.80 mmol) in anhydrous CH2Cl2(50 mL) proceeded with stirring and cooling for 30 min. The reaction was addedby 13 and stirred at roomtemperature for 10 h. The white solid formed was filtrated to give part ofphenylacetamide 15. The filtrate was washed with waterand dried over anhydrous Na2SO4 and evaporated. Theresidue was chromatographed to give another part of 15. Et3N (10.55 g, 104.38 mmol) was added to asuspension of 15 (12.28 mmo) inacetic anhydride (15.65 g, 153.51 mmol) under nitrogen atmosphere at 0 ¡ãC. The mixture was stirred at 75 for 4 h and concentrated in vacuum. Water and CH2Cl2were added to the residue, and the organic layer was separated, washed withbrine, dried over anhydrous Na2SO4 andconcentrated. The resulting residue was triturated with diethyl ether (20 mL)and filtrated to give 16. To asuspension of 16 (21.87 mmol) inanhydrous CH3OH (120 mL), 28percent sodium methoxide in CH3OH(4.76 g, 22.97 mmol) was added slowly under nitrogen atmosphere at 0 ¡ãC. Thereaction was stirred at the same temperature for 1 h and acetic acid (1.48 g,22.97 mmol) was added slowly. The mixture was concentrated in vacuum and theresidue was diluted with CH2Cl2. The organic layer waswashed with water, dried over anhydrous Na2SO4 andconcentrated in vacuum. The resulting solid was triturated with diethyl ether(30 mL) and filtrated to give 17 as a pale yellow solid. NaH (0.13 g,3.25 mmol) was added to the solution of 17(1.28 mmol) in anhydrous DMF (5 mL) at 0 ¡ãC. The reaction was stirred at the sametemperature for 30 min, diluted with ethyl acetate (100 ml) and washed withwater (3 ¡Á 30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated todryness. 18 was obtained by a silicagel column chromatography as a yellow solid. A mixture of 18 (4.96 mmol), K2CO3 (0.69 g, 4.96 mmol),TBAB (0.16 g, 0.5 mmol) and 1,4-dibromobutane (4.28 g, 19.84 mmol) in CH3CN(20 mL) was stirred at 45 ¡ãC. The solvent was removed and the residue was diluted withethyl acetate (100 mL) and washed with water (3¡Á 30 mL). Theorganic layer was dried over anhydrous Na2SO4and concentrated. Intermediate 19was obtained by a silica gel column chromatography. To a solution of 19 (0.37 mmol) in CH3CN (5mL) were added KI (0.11 g, 0.75 mmol), K2CO3 (0.093 g,0.56 mmol) and substituted aromatic sulfonamide (0.56 mmol ). The reaction wasstirred in the refluxing CH3CN overnight. The solvent wasconcentrated and the residue was diluted with ethyl acetate (50 mL) and washed withbrine. The organic layer was dried over anhydrousNa2SO4 and concentrated in vacuum followed by a silicagel column chromatography to yield compounds 20a-m.

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Xinrui; Lu, Peng; Xue, Xiaojian; Qin, Hui; Fan, Chen; Wang, Yubin; Zhang, Qi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 849 – 853;,
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