Month: March 2021

These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-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. Safety of 5-Amino-2-fluorobenzamide

A mixture of 5-benzyloxy-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzoic acid (40 mg, 0.082 mmol), 5-amino-2-fluoro-benzamide (14 mg, 0.09 mmol), HATU (38 mg, 0.10 mmol) and DIPEA (50 mu, 0.2871 mmol) in DMF (700 mu was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and the precipitated solid was filtered and washed with water. The solid was taken up in DCM, dried over MgSO/i, filtered and concentrated in vacuo. Product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford 5-benzyloxy-N-(3-carbamoyl-4-fluoro-phenyl)-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzamide (28 mg, 52%). ESI-MS m/z calc. 626.11, found 627.2 (M+l)+; retention time (Method B): 2.09 minutes (3 minutes run). NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 7.89 (dd, J = 6.4, 2.8 Hz, 1H), 7.74 (d, J = 6.7 Hz, 1H), 7.71 – 7.63 (m, 3H), 7.36 – 7.18 (m, 6H), 7.09 – 7.04 (m, 2H), 6.97 – 6.92 (m, 2H), 5.17 (s, 2H) ppm.

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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Related Products of 207405-68-3,Some common heterocyclic compound, 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H22N2O2, 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: Azabicyclic amine (7a-c, 1.2 mmol) and Hunig?s base (4.0 mmol) were added to a solution of compound (4or 5, 1.0 mmol) in n-BuOH (2 ml) and the resulting mixture was stirred at reflux for 1 day. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was purified by column chromatography (CHCl3/MeOH 200:1) to obtain product.

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 endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.

Reference:
Article; Pham, Tuan-Anh N.; Yang, Zunhua; Fang, Yuanying; Luo, Jun; Lee, Jongkook; Park, Haeil; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1349 – 1356;,
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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 1943-79-9 as follows. category: amides-buliding-blocks

General procedure: alpha-amino methyl ester hydrochloride (2 mmol) and carbamate (2.2 mmol) were dissolved in amixture of acetonitrile (12 ml) and triethylamine (6 ml) and reaction mixture was refluxed for 10h. Then, NaOH (5 mmol) was added and reaction was continued for another 8 hours. After thecompletion of the reaction, solvents were distilled off, and the residue was partitioned betweenethyl acetate and 0.1N aqueous HCl and extracted. The organic layer was washed with brine followed by drying over anhydrous Na2SO4. The concentration of the organic layer gave thecrude product which was purified either by recrystallization (hexane-ethyl acetate mixture) or bycolumn chromatography (hexane:ethylacetate) to afford the desired product.

According to the analysis of related databases, 1943-79-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanwar, Dinesh Kumar; Ratan, Anjali; Gill, Manjinder Singh; Synlett; vol. 28; 17; (2017); p. 2285 – 2290;,
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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. 79722-21-7, name is tert-Butyl benzyloxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl benzyloxycarbamate

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

The synthetic route of 79722-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
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Related Products of 1346674-23-4, 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. 1346674-23-4, name is 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0298] Example 10B (0458) [0299] Compound 170 was prepared from compounds 160 and 100 as follows: (0459) (0460) [0300] Potassium carbonate (20.3 g, 1.5 eq., 147 mmol), compound 100 (19 g, 1.1 eq., 108 mmol), compound 160 (20 g, 1 eq., 97.9 mmol), DPPF ligand (2.2 g, 0.04 eq., 3.9 mmol), and Pd(OAc)2 catalyst (0.44 g, 0.02 eq., 2 mmol) were charged to a reactor. THF (200 mL, 10 mL/g) was charged to the reactor with agitation. The reactor was evacuated and filled with N2 three times and the contents were then heated to 68C with reflux. The reactor was sampled at 22 hours and the compound 160 content was 0.9 area% by HPLC. The reactor contents were cooled to 65C and water (200 mL, 10 mL/g) was charged to the reactor over 4 hours and the reactors contents were then held at 20C for a minimum of 3 hours. The reactor contents were filtered and compound 170 was collected as a solid. The solid compound 170 was rinsed with THF/water (1 : 1 mixture, 200 mL, 10 mL/g). The washed solids were dried under vacuum with N2 purge at 22 C for a minimum of 3 hours. A yield of 84% was obtained with 99 area% by HPLC (245 nm), 79 ppm Pd and 0.2% residue on ignition (“ROI”). Of the impurities, 0.51 A% regioisomer and 0.33%> bis-coupling product were found: (0461) (0462) Regioisomer Bis-Coupling Impurity (0463) [0301] The method was repeated on a 40 g scale (based on compound 160). The coupling reaction was performed using compound 100 (1.1 eq.), Pd(OAc)2 (0.02 eq.), dppf in THF (0.04 eq., 10 mL/g) at 68 C for 28 h to reach 98.4% conversion. Water was added (350 mL) to the reaction mixture over 3 h and aged at 65 C for 10 h, cooled to 20 C in 1.5 h and aged for 16 h. After filtration and drying, a beige solid compound 170 was obtained (57.2 g, 85%, 98.6A%, 0.55A% regioisomer, 0.48A% bis-coupling impurity, 87 ppm Pd and 0.3% ROI). (0464) [0302] The method was repeated on a 609 g scale (based on compound 160). (0465) Potassium carbonate (0.6114 kg, 1.5 eq., 4.34 mol), compound 100 (0.7769 kg, 1.5 eq., 4.41 mol), compound 160 (0.6099 kg, 1 eq., 2.99 mol), DPPF ligand (0.0662 kg, 0.04 eq., 0.119 mmol), and Pd(OAc)2 catalyst (0.0137 kg, 0.02 eq., 0.061 mmol) were charged to an isolator. A reactor was evacuated and filled with N2 three times and charged with the contents of the isolator. THF (10.35 kg, 20 L/kg) was charged to the reactor with agitation. The reactor contents were heated to 68C with reflux. The reactor was sampled at 40 hours and the compound 160 content was 0.3 area% by HPLC. The reactor contents were cooled to 65C and water (6.01 kg, 10 L/kg) was charged to the reactor over 3 hours and the reactor contents were then held at 20C for a minimum of 3 hours. The reactor contents were filtered and compound 170 was collected as a solid. The solid compound 170 was rinsed with THF/water (1 : 1 mixture, 6 L, 10 mL/g). The washed solids were dried under vacuum with N2 purge at 22C for a minimum of 10 hours. A 84% yield (0.8576 kg) was obtained with 99.2 A% by HPLC (245 nm), 24 ppm Pd and less than 0.1% ROI.

The synthetic route of 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BEAUDRY, Danial; CRAVILLION, Theresa; GOSSELIN, Francis; LIM, Ngiap-Kie; MALHOTRA, Sushant; TIAN, Qingping; ZHANG, Haiming; GMEHLING, Alexander; FETTES, Alec; BACHMANN, Stephan; (130 pag.)WO2018/109050; (2018); A1;,
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Application of 14719-21-2, A common heterocyclic compound, 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, molecular formula is C5H4F3NO, 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.

A solution of compound 61 (80 mg, 0.13 mmol), N-propargyltrifluoroacetylamide (196 mg, 1.30 mmol), tetrakis(triphenylphosphine)-palladium(0) (30 mg, 0.026 mmol), Cul (9.9 mg, 0.052 mmol), and Et3N (80 muGamma) in anhydrous DMF (3.0 mL) was stirred at 50C for 12 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to yield 5-{(5)-l-[5-methoxy-4-(3-trifluoroacetamido-l-propynyl)-2-nitrophenyl]-2,2-dimethyl-propyloxy}methyl-2′-deoxyuridine 62 (75 mg, 90%). 1H NMR (400 MHz, MeOD-d4): 5 8.1 1 (s, 1 Eta, Eta-6), 8.08 (s, 1 Eta, Ph-H), 7.36 (s, 1 H, Ph-H), 6.27 (t, 1 H, J = 6.4 Hz, Eta-Gamma), 5.33 (s, 1 H, Ph-CH), 4.47 (m, 1 H, H-3′), 4.44 (s, 2 H, 5-CH2), 4.32 (d, 2 H, J = 2.0 Hz, CH2), 4.08 (s, 3 H, OCH3), 3.99 (m, 1 H, H-4′), 3.87 (m, 1 H, H-5’a), 3.79 (m, 1 H, H-5’b), 2.30 (m, 2 H, H-2), 0.93 (s, 9 H, C(CH3)3).

The synthetic route of 14719-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); 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 915087-25-1 as follows. HPLC of Formula: C8H9FN2O

Synthesis of 4-(2-cyano-2-hexadeuteropropylamino)-2-fluoro-N-methyl benzamide (compound 28) TMSCN (2.1 g, 21.2 mmol), compound 5 (0.7 g, 4.2 mmol) and deuterated acetone (1.5 g, 23.4 mmol) were placed in a microwave reaction tube, and the mixture was heated to 80C by microwave, and reacted for 3 h, power 50 W. The mixture was cooled to room temperature, deuterated acetone was removed under reduced pressure, and water was added (20 mL). The resulting mixture was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated. The resulting solid was washed with petroleum ether (10 mL) and dried by suction to give compound 28 as a white solid (870 mg, 86.6% yield). 1H NMR (CDCl3, 400 MHz): delta(ppm) 7.98 (1H, t, J = 8.4 Hz), 6.64 (1H, s), 6.62 (1H, d, J = 4 Hz), 6.58 (1H, s), 4.37 (1H, s), 3.00 (3H, s).

According to the analysis of related databases, 915087-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HC Pharmaceutical Co., Ltd.; CHEN, Yuanwei; EP2792674; (2014); 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. 24167-56-4, name is 4-Fluoro-N,N-dimethylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Fluoro-N,N-dimethylbenzamide

EXAMPLE 7 A solution of 758 mg. of N,N-dimethyl-4-fluorobenzamide and 0.44 ml. of phosphorous oxychloride in 50 ml. of 1,2-dichloroethane is refluxed for one hour. To this solution is added a solution of 500 mg. of isopropyl 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 10 ml. 1,2-dichloroethane. The reaction mixture is refluxed for 3 hours. A solution of 3.3 g. sodium acetate trihydrate in 9 ml water is added and refluxed for a further 10 hours. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is purified by preparative t.l.c. using hexane:ethyl acetate (90:10). Crystallization from dichloromethane-hexane yields isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate (XI, R=H, L=p-F, R2 =iC3 H7, n=1), m.p. 92 C.

The synthetic route of 24167-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Syntex (U.S.A.) Inc.; US4410534; (1983); A;,
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Some common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, molecular formula is C9H20N2O2, 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. category: amides-buliding-blocks

N-(4-ftuoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine (1.3 g, 3.43 mmol), DIPEA (2.2 gl, 7.14 mmol) and tert-butyl methyl(2-(methylamino)ethyl)carbamate (0.77 g, 4.12 mmol) were dissolved in DMA (15 mL). After heating up to 100 ¡ãC overnight, the reaction solution was concentrated and purified by column chromatography to obtain tert-butyl {2-[(4-{[4-(1H-indol-3-yl)pyrimidin-2-yl]amino}-5-methoxy-2-nitrophenyl)(methyl)am ino]ethyl}methylcarbamate (1.9 g, 80percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 112257-19-9, its application will become more common.

Reference:
Patent; Shanghai Hansoh Biomedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; WEI, Mingsong; SUN, Guangjun; TAN, Songliang; GAO, Peng; WANG, Shaobao; XIU, Wenhua; ZHANG, Fujun; BAO, Rudi; (183 pag.)EP3205650; (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. 1280210-80-1, name is MK-3102 interMediate3, This compound has unique chemical properties. The synthetic route is as follows., name: MK-3102 interMediate3

To a solution of 11 (260 mg, 0.69 mmol) in DMAc (1 mL) was added Ml (288 mg, 0.84 mmol) followed by Ets (0.15 mL, 1.04 mmol) and stirred it for 5 minutes. AcOH (0.10 mL, 1.74 mmol) was added to the reaction mixture and continued the stirring for 30 minutes. NaBH(OAc)3 (0.44 g, 2.09 mmol) was added to the reaction mixture and continued the stirring for 2 days. The reaction mixture was quenched with NH4OH and extracted with EtOAc. Combined organics were concentrated under vacuum. Crude mixture was purified by silica gel chromatography afforded 12. XH NMR (400 MHz, CDC13): delta 7.68 (br. s., 1H), 7.36 – 7.48 (m, 1H), 7.17 – 7.30 (m, 2H), 7.05 (dt, J= 4.40, 8.80 Hz, 1H), 6.91 (d, J= 7.04 Hz, 2H), 6.69 (ddd, J= 3.08, 5.50, 8.73 Hz, 1H), 4.65 (br. s., 1H), 4.55 (br. s., 1H), 4.29 (d, J= 8.22 Hz, 1H), 4.04 (br. s., 2H), 3.59 – 3.82 (m, 2H), 3.30 (s, 3H), 2.47 (br. s., 1H), 1.93 – 2.05 (m, 1H), 1.39 (s, 9H).; Molecular Formula: C27H30F2N4O4S; LCMS purity: 84.2%; Expected: 544.2; Observed: 545.2 (M+l).

According to the analysis of related databases, 1280210-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; WO2014/18350; (2014); A1;,
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