Category: amides-buliding-blocks

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. 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

3,8-diazabicyclo [3.2.1] octane-3-carboxylic acid tert-butyl ester (318 mg, 1.5 mmol)And 2-chloro-5- (chloromethyl) erythropine (243 mg, 1.5 mmol) were dissolved in acetonitrile (50 mL)Potassium carbonate (414 mg, 3.0 mmol) was added and reacted at 70 C for 16 hours.After cooling to room temperature, ethyl acetate (10 mL) and water (50 mL) were added,The aqueous phase was extracted with ethyl acetate (150 mL X3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (480 mg, 95% yield) as a pale yellow oil.

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

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H10N2O3S

2 mmol compound 1a or 1b and 0.194 g (2 mmol) potassiumthiocyanate in about 25 mL acetone were refluxed for 30 min. Theresulting solid (KCl) was removed by filtration. Then to this solutioncorresponding sulfonamides (2 mmol) in about 10 mL acetone wasadded dropwise, the mixture was stirred under reflux for 2 h. The resulting solution was evaporated under reduced pressure. Then,the residue was treated with the water to give crude product as awhite solid. The resulting crude product was stirred with diethyletherat room temperature for 1 h and then filtered. After theseexperimental procedures, the white colored substance was obtainedas pure.

According to the analysis of related databases, 144-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koca, ?rfan; Yi?itcan, Serhat; Guemue?, Mehmet; Goekce, Halil; Sert, Yusuf; Journal of Molecular Structure; vol. 1204; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, belongs to amides-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. Safety of tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate

Ste 2: Synthesis of S 14 To a round-bottom flask, S 13 (276 mg, 1.0 mmol) was dissolved in 3.0 mL of anhydrous DMF. Amine (320 mg, 1.0 mmol) and DIPEA (259 mg, 2.0 mmol) were added. The reaction mixture was stirred at 90 C for 12 h. The mixture was cooled to room temperature, poured into water and extracted with ethyl acetate for two times. The combined organic layer was washed with brine, dried over anhydrous Na2S04. After filtration and evaporation, the crude residue was purified by HPLC with H20/ MeCN to give compound S 14 as colorless oil (172 mg, 30% yield). ESI-MS calculated for C28H4iN409 [M+H]+ = 577.2; Observed: 577.3.

The synthetic route of 194920-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; LI, Yangbing; AGUILAR, Angelo; ZHOU, Bing; HU, Jiantao; XU, Fuming; QIN, Chong; HU, Yang; XIANG, Weiguo; REJ, Rohan; YANG, Jiuling; HAN, Xin; BAI, Longchuan; YANG, Chao-Yie; (252 pag.)WO2017/176958; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 535170-20-8, name is tert-Butyl (3-amino-2,6-difluorophenyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl (3-amino-2,6-difluorophenyl)carbamate

The tert-butyl-3-amino-2,6-difluorophenylcarbamate (100 mg, 0.41 mmol) prepared at Step 3 was added and dissolved into dichloromethane solvent. 2- propane sulfonyl chloride (50 uL, 0.45 mmol) and pyridine (36 uL, 0.045mmol) were added into the reaction solution and stirred at 50C for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 94 mg of the target compound, tert-butyl-2,6-difluoro-3-(1-methylethylsulfonamido)phenylcarbamate (percentage yield: 65%), was obtained.1H NMR(400MHz, CDCl3): delta 7.43(td, J = 8.8, 5.6 Hz, 1H), 6.97(bs, 1H), 6.90(td, J = 8.8, 1.6 Hz, 1H) 6.33(bs, 1H), 3.25(m, 1H), 1.49(s, 9H), 1.39(d, J = 6.8 Hz, 6H).

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 535170-20-8.

Reference:
Patent; Youai Co., Ltd.; SHIM, Eun Kyong; KIM, Nam Doo; SHIM, Tae Bo; KIM, Seung Yong; EP2647637; (2013); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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.

HTP Assay of CHMO Polypeptides: (0203) Primary screening used to guide optimization was carried out in a 200 muL volume in 96-well plate high-throughput (HTP) assay protocol using cell lysates. The general HTP assay conditions were: 1-100 g/L substrate (i.e., compound (1a) or (1b)), 10-200 muL of clear cell lysate containing the engineered CHMO polypeptide, 0.05-1.0 g/L NADP cofactor, 1 g/L ketoreductase (KRED) polypeptide for cofactor recycling, 0.025-0.100 M phosphate or TEA buffer solution containing 3.5%-10% (v/v) IPA (and optionally, 1.5% acetone or 10% PEG200) co-solvent, pH 8-9, 25 C. reaction temperature and 20 h reaction time (with 200 rpm shaking). The HTP assay conditions were changed slightly over the different rounds of the directed evolution of the CHMO variant polypeptide disclosed in order to detect those variants most improved in enzyme properties. Table 4 shows the HTP assay conditions used to perform primary screening of those variant polypeptides whose improved properties were confirmed by SFP assay as summarized in Tables 2A and 2B. Rounds 1-6 assays used the amide substrate of compound (1a) and Rounds 7-16 assays used the acid substrate of compound (1b). HTP Assay Results: (0220) Representative results in the primary screening using the HTP assay for both the amide substrate (compound (10) and the acid substrate (compound (2a)) are shown below in Tables 7 and 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; CODEXIS, INC.; Ang, Ee Lui; Alvizo, Oscar; Behrouzian, Behnaz; Clay, Michael; Collier, Steven; Eberhard, Ellen; Fu, Fan Jaslyn; Song, Shiwei; Smith, Derek; Widegren, Magnus; Wilson, Robert; Xu, Junye; Zhu, Jun; (200 pag.)US9267159; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, belongs to amides-buliding-blocks compound, 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 143557-91-9, category: amides-buliding-blocks

To a stirred solution of Intermediate 63 (0.68 g, 2.98 mmol) in dry DMF (10 mL) wasadded NaH (60 % dispersion in mineral oil,120 mg, 3.00 mmol). After the mixturewas stirred for 15 mm Intermediate 26 (0.5 g, 2.29 mmol) was added as one portion. The resulting mixture was stirred at RT for 48 h. The reaction mixture was poured onto brine and extracted into EtOAc. The organic layer was washed with brine, separated, dried over MgSO4, filtered and concentrated under reducedpressure to give brown oil. The crude material was purified by Biotage Isolera chromatography (silica gel, eluting with heptane-EtOAc, 1:0 to 0:1) to afford 531 mg (54% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 7.71 (t, J = 1.4 Hz, 2H), 7.68 – 7.63 (m, 1H), 7.53 (d, J = 1.2 Hz, 1H), 7.13 (dd, J = 2.4, 1.3 Hz, 1H), 4.75 (tt, J = 10.6, 5.9Hz, 1H), 4.34 (5, 2H), 2.53 (d, J = 1.1 Hz, 3H), 2.20- 2.00 (m, 4H), 1.93 – 1.65 (m,4H), 1.49 (5, 9H).LCMS (Analytical Method A) Rt = 1 .46 mm, MS (ESIpos): m/z = 426.05 (M+H)+.

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; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 20188-40-3,Some common heterocyclic compound, 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, molecular formula is C8H11ClN2O, 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.

Ethyl 2-(2-fluoro-4-propylphenoxy)-4-formylnicotinate (0.13 g) obtained in Reference Example 319 was dissolved in methanol (3 mL), 4-(aminomethyl)benzamide hydrochloride (0.082 g), acetic acid (0.024 g) and triethylamine (0.061 g) were added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added sodium tetrahydroborate (0.15 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by NH silica gel chromatography (hexane-ethyl acetate), and recrystallized from ethyl acetate-ethanol to give the title compound (0.079 g). MS: [M+H]+ 420.2 1H NMR (300 MHz, DMSO-d6) delta0.93 (3H, t, J = 7.3 Hz), 1.63 (2H, sxt, J = 7.4 Hz), 2.56-2.65 (2H, m), 4.48 (2H, s), 4.76 (2H, s), 7.02-7.14 (1H, m), 7.16-7.28 (2H, m), 7.34 (2H, d, J = 5.1 Hz), 7.38 (2H, d, J = 8.3 Hz), 7.87 (2H, d, J = 8.3 Hz), 7.94 (1H, brs), 8.20 (1H, d, J = 5.1 Hz).

The synthetic route of 20188-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 154350-29-5, These common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, 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 an iced slurry of cyclopropanesulfonamide (1.21 g, 9.99 mmol), Triethylamine (2.95 mL, 20.97 mmol), and 4-Dimethylaminopyridine (0.061 g, 0.499 mmol) in CH2Cl2 (50 mL) was added solution of Di-tert-butyl dicarbonate (2.423 mL, 10.99 mmol) in DCM (10 mL) dropwise. The formed solution was stirred at room temperature overnight, Removed the solvent in vacuo. The residual oil was taken up in EtOAc and washed with 1M HCl and brine. Dried over MgSO4, filtered, and concentrated. The residue was purified by Biotage column, eluted with gradient 5percent50percent acetone-hexane to yield the desired produce tert-butyl cyclopropylsulfonylcarbamate (2.17 g, 9.61 mmol, 96percent yield) as a viscous oil, which solidified upon standing on bench. 1H NMR (400 MHz, CDCl3) ppm 1.11-1.13 (m, 2H) 1.37-1.39 9m, 2H) 1.53 (s, 9H), 2.89-2.92 (m, 1H) 7.00-7.05 (b, NH).

The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/150866; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 3984-14-3, These common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, 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.

EXAMPLE 5 (+/-)8-cyclohexyl-N-[(dimethylamino)sulfonyl]-1,1a,2,12b-tetrahydro-1a-(4-morpholinylcarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxamide. A 2M solution of oxalyl chloride (0.093 mL, 0.186 mmol) in CH2Cl2 was added dropwise to a solution of (+/-)-8-cyclohexyl-1,1a,2,12b-tetrahydro-1a-(4-morpholinylcarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (45 mg, 0.093 mmol) in CH2Cl2 (10 mL), containing one drop of DMF. The reaction mixture was stirred at rt. for 2 hr., after which it was concentrated and dried under high vacuum. The residue was subsequently dissolved in THF (10 mL) and a solution of N,N-dimethylsulfonamide, (23 mg, 0.186 mmol) and DIPEA (0.049 mL, 0.279 mmol)) in THF (2 mL) was added. This was followed by the addition of DMAP (10 mg), after which the reaction was stirred at rt. for 10 min., and then at 50 C. overnight. It was then cooled, and the mixture concentrated under reduced pressure. The resultant residue was purified by preparative reverse phase HPLC to afford the product as a yellow solid, (5.0 mg, 9% yield). MS m/z 591(MH+), Retention time: 3.525 min; 1H NMR (300 MHz, CD3OD) delta ppm. Compound was observed to exist as inter-converting rotamers, as evidenced from the compound’s NMR spectrum.

The synthetic route of 3984-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/60565; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 138-41-0, name is Carzenide, 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 Carzenide

Compound 3-7 (300 mg, 1.33 mmol), p-sulfonamide benzoic acid (294 mg, 1.46 mmol, 1.1 eq.), HOBt (539 mg, 3.99 mmol, 3 eq.) and EDCI (765 mg, 3.99 mmol, 3 eq.) in 50 mL Single mouth bottle,DMF and TEA (0.74 mL, 5.32 mmol, 4 eq.) were added.Stir at room temperature overnight. TLC tracking monitoring. Rotate the DMF,Add EA and water for extraction, wash with saturated brine, dry, spin dry, and pass through column (DCM:acetone = 3:1). A white solid of 450 mg was obtained in a yield of 83%.

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

Reference:
Patent; Guangzhou Hengnuokang Pharmaceutical Technology Co., Ltd.; Zhang Jiancun; Lin Cai; Zou Qingan; (45 pag.)CN108456208; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics