Category: amides-buliding-blocks

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;,
Amide – Wikipedia,
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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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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – 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 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1314538-55-0,Some common heterocyclic compound, 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, molecular formula is C6H12BF3KNO2, 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.

102201 Into a reaction vessel was placed, compound 14-4, prepared in accordance with Example13, (52 mg, 0.1 mmol), commercial Potassium N-Boc-amino-methyltrifluoroborate (47 mg, 0.2 mmol), Cs2CO3 (97 mg, 0.3 mmol), Pd(dppf)C12 CH2C12 Adduct (8.1 mg, 9.93 jimol) dissolved in degassed water (0.5 ml) and 1 ,4-dioxane (5 ml). The mixture was heated to 90 C overnight, cooled to room temperature (rt) and diluted with EA, then washed with water brine and dried over Na2504. After filtration and concentration, the crude residue was taken up with DCM (5 mL), then TFA (1 mL) was added. The mixture was stirred at rt for 1 hour and concentrated. The concentrate was purified by reverse phase chromatography (5-75% MeCN in water w/ 0.1% TFA, C 18 column) to yield 19-1 as the TFA salt. ?H NMR oe (ppm)(DMSO-d6): 7.89 (1 H, d, J = 5.79 Hz), 7.71-7.77 (2 H, m), 7.46 (1 H, t, J = 7.75 Hz), 7.37 (1 H, d, J = 7.65 Hz), 7.09 (1 H, d, J = 10.04 Hz), 6.92 (1 H, dd, J = 7.92, 1.98 Hz), 6.58 (1 H, dd, J = 8.02, 2.48 Hz), 5.88-5.93 (1 H, m), 4.24- 4.33 (2 H, m), 2.45 (3 H, s), 1.93 (3 H, d, J = 7.08 Hz). HRMS C22H20F2N4045 [M+H] calc:475.1246, obs: 475.1242

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PERO, Joseph, E.; LEHMAN, Hannah, D. G. F.; KELLY, Michael, J., III; ZHAO, Lianyun; ROSSI, Michael, A.; LI, Dansu; GILBERT, Kevin, F.; WOLKENBERG, Scott; MULHEARN, James; LAYTON, Mark, E.; DE LEON, Pablo; WO2014/66490; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 4-(hydroxymethyl)benzylcarbamate

EXAMPLE 8-1 4- {[(tert-butoxycarbonyl)amino]methyl} benzyl(3aR, 7aR)-1 -(7H-pyrrolo[2,3-d]pyrimidin-4-yl)octahydro-4-pyrrolo[3,2-b]pyridine-4-carboxylate To a stirred solution of CDI (20 mg, 0.12 mmol) in THF (0.20 mL) was added (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (29 mg, 0.12 mmol) in THF (0.20 mL) at -10 C. The resulting suspension was allowed to stir for 1 hour at ambient temperature. In a separate flask, enantiomer 2 of Example 2 was dissolved in THF (0.20 mL) and DBU (0.019 mL, 0.12 mmol) followed by Et3N (0.017 mL, 0.12 mmol) was added and allowed to stir at ambient temperature for 5 minutes. The activated alcohol solution was added to the suspension of amine in DBU and the resulting suspension was allowed to stir at ambient temperature for 18 hours. The reaction mixture was partitioned between EtOAc (25 mL) and saturated aqueous sodium bicarbonate (25 mL). The layers were separated, and the organic layer was collected, dried over sodium sulfate, and concentrated in vacuo. The crude reaction mixture was purified by column chromatography on silica gel eluting with EtOAc/hexane (0-100%) followed by DCM:MeOH (90:10). The product fractions were concentrated in vacuo to afford the desired product. LRMS calc’d for C27H34N6O4 [M+H]+, 507; found 507. Jak1 activity: +.

The synthetic route of 123986-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 112253-70-0, name is 2-Amino-4-bromobenzamide, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrN2O

2-Amino-4-bromobenzonitrile was dissolved in 4: 1 AcOHZH2SO4 to form a suspension. The mixture was stirred for 4 h until it became clear and all starting material was consumed as monitored by LC-MS. The solution was poured into ice water and extracted by EtOAc three times. The combined organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed to provide 11-1. Substituted benzyloxy acetic acid (1.1 equiv) was treated with 2 M oxalyl chloride in DCM for 3 h and concentrated to give the corresponding acid chloride, which was then added to a stirred solution of 11-1 and pyridine (5 equiv) in DCM. The reaction mixture was stirred for 3 h until 11-1 was consumed as monitored by LC-MS. The precipitate was collected by filtration and was dried under vacuum to provide 11-2 as white solid. 11-2, potassium carbonate (4 equiv), boronic ester (1.5 equiv) and Pd(PPh3 )4( 10%) were dissolved in 4: 1 dioxane/water and sealed in a microwave tube. The reaction mixture was degassed and heated by microwave for 30min at 140 0C. The solvent was removed and the residue was subjected to preparative HPLC to provide product 11-3 as a TFA salt.

The synthetic route of 112253-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; LOGRASSO, Philip; BANNISTER, Thomas; SCHROETER, Thomas; FANG, Xingang; YIN, Yan; CHEN, Yen Ting; SESSIONS, Hampton; CHOWDHURY, Sarwat; LUO, Jun-Li; VOJKOVSKY, Tomas; WO2010/56758; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics