Tag: M.W=100-200

Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. SDS of cas: 103361-99-5

c. 7-fluoro-4-isobutyl-2H-1,4-benzoxazin-3(4H)-one To 3.96 g (99 mmol) of hexanes washed 60% sodium hydride in 150 ml of N,N-dimethylformamide was added portionwise as a solid 15 g (90 mmol) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one. When the addition was complete the reaction was stirred at room temperature for 10 min, after which time 19.8 g (108 mmol) of isobutyl iodide was added. The reaction was then stirred overnight before quenching into 200 ml of water. The aqueous phase was extracted with EtOAc (2*150 ml) and the combined organics were dried over Na2 SO4, filtered and evaporated in vacuo to give the desired alkylated product, as a yellow oil (13 g, 65% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US5393735; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1237535-78-2, The chemical industry reduces the impact on the environment during synthesis 1237535-78-2, name is 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, I believe this compound will play a more active role in future production and life.

Example 2: Synthesis of compounds 2.1-2.37 Step A: (1S,1aS,6bR)-5-((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylic acid ethyl ester Intermediate III (400mg, 1.8mmol), 5-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one (250mg, 1.5mmol), and cesium carbonate (801mg, 2.3mol) in DMF (20mL) was stirred at 120C for 2 hours. The reaction mixture was washed with water (10mL). The reaction was diluted and extracted with ethyl acetate (2 × 10mL). The combined organic extracts were washed with brine (20mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (PE:EtOAc = 3:1 elution) to give the target compound as a white solid (360mg, 54.6%).

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, 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BeiGene, Ltd.; Zhou, Changyou; Wang, Shaohui; Zhang, Guoliang; (104 pag.)CN105348299; (2016); A;,
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. 154350-29-5, name is Cyclopropanesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 154350-29-5

14-tert-Butoxycarbonylamino-18-(tert-butyl-dimethyl-silanyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for 2 h, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). The reaction mixture was stirred for 4 h at rt, and the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product. It was then purified by flash chromatography (eluding with 33percent ethyl acetate in hexane) to give 300 mg (51percent) of [18-(tert-butyl-dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester as a white solid. 1H NMR (300 MHz, CD3OD) delta 1H 0.07 (s, 3 H), 0.08 (s, 3 H), 0.85 (s, 9 H), 0.87-1.49 (m, 21 H), 1.73-1.95 (m, 3 H), 2.08-2.16 (m, 1 H), 2.25-2.36 (m, 2 H), 2.42-2.56 (m, 1 H), 2.85-2.93 (m, 1 H), 3.65-3.74(dd, J=10.61, 3.66 Hz, 1 H), 3.89 (d, J=10.25 Hz, 1 H), 4.34 (m, J=9.70, 9.70 Hz, 1 H), 4.43 (t, J=7.87 Hz, 1 H), 4.57 (s, 1 H), 4.94-5.01 (m, 1 H), 5.10 (d, J=8.78 Hz, 1 H), 5.66-5.75 (m, 1 H), 6.55 (s, 1 H), 10.13 (s, 1 H); MS m/z 683 (M++1).

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; Bristol-Myers Squibb Company; US2007/93414; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14062-80-7, name is 4-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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. HPLC of Formula: C9H10ClNO

General procedure: To a mixture of 1a (0.6g, 4.8 mmol, 1equiv), imidazolium chloride (0.25g, 2.4 mmol,0.5equiv) and N,N-dimethylbenzamide (1.43g, 9.6 mmol, 2 equiv) was added. Themixture was stirred at 160C for 10h. after completion of the reaction. 15ml water was added and the resulting mixture was extracted with 20ml EA thrice, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using PE/EA as eluent to obtain thepure desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-80-7, its application will become more common.

Reference:
Article; Tian, Qingqiang; Luo, Wen; Gan, Zongjie; Li, Dan; Dai, Zeshu; Wang, Huajun; Wang, Xuetong; Yuan, Jianyong; Molecules; vol. 24; 1; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 13621-50-6, 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. 13621-50-6, name is Ethyl 3-amino-3-thioxopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

(step 6) A solution of the compound (107 mg, 0.30 mmol) obtained in step 5 and methyl 3-amino-3-thioxopropanoate (48.7 mg, 0.37 mmol) in EtOH (3 mL) was stirred at 90C for 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 5?80% ethyl acetate/hexane) to give a crude product ethyl 2-(4-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-2-yl)acetate as a colorless oil, which was used for the next step without purification. MS (API) :400(M+H)

The chemical industry reduces the impact on the environment during synthesis Ethyl 3-amino-3-thioxopropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; OCHIDA, Atsuko; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; MIURA, Shotaro; YONEMORI, Kazuko; KOYAMA, Ryokichi; EP2738170; (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. 433-14-7, name is 4-Fluoro-N-methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., name: 4-Fluoro-N-methylbenzenesulfonamide

A mixture of 4-fluoro-N-methyl-benzenesulfonamide (0.50 g, 2.64 mmoi), 1,4-dioxa-8-azaspiro[4.5]decane (0.76 g, 5.28 rnmoi) and potassium carbonate (0.73 g, 5.28 mrnoi) in amixed solvent of acetonitrile (10 mL) and 1 ,3-dimethythexahydropyrimidin-2-one (20 mL) was heated with stirring at 65 C for 3 hrs, The resulting reaction mixture was cooled to rt, dilutedwith water (50 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 4-(1 ,4-dioxa-8-azaspiro [4.5] decan-8-yl)-N-methyl-benzenesulfonamide (0.60 g), which was used in the next step without further purification.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, 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 122334-37-6, Computed Properties of C9H10ClNO2

General procedure: A dry round-bottom flask under an atmosphere of argon was charged with alkyne (1 mmol), Weinreb amide (1.2 mmol), Ti(OiPr)4 (1.5 mmol, 0.44 mL), and anhydrous Et2O (10 mL). To this stirring mixture was injected i-PrMgCl (2M in Et2O, 3 mmol, 1.5 mL) dropwise over 5 minutes, the reaction was stirred for 4 hours at room temperature. The round-bottom flask was then placed in a dry-ice acetone bath and equilibrated to -78 C. In a separate dry pear-shaped flask under an atmosphere of argon BF3?OEt2 (2 mmol, 0.247 mL) was injected into a solution of aldehyde (2 mmol) in Et2O (2 mL) precooled with a dry-ice acetone bath. The BF3?OEt2-aldehyde mixture was stirred for 30 seconds then pulled up into a syringe. The solution of complexed aldehyde was then injected into the cooled reaction mixture containing the titanacycle. The cooling bath was removed and the reaction was allowed to warm to room temperature over 2 hours. At which point the reaction was quenched with 1 mL H2O, dried over magnesium sulfate, filtered, and concentrated. The crude material was subjected to flash chromatography (hexanes/CH2Cl2: 90/10).

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, 4-Chloro-N-methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Silwal, Sajan; Rahaim, Ronald J.; Tetrahedron Letters; vol. 56; 42; (2015); p. 5738 – 5742;,
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. 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, A new synthetic method of this compound is introduced below., Formula: C6H11NO2

To the reaction flask, 2-(2-methoxyphenoxy)tetrahydropyran (8B) (200 g, 0.96 mol) and tetrahydrofuran (1000 ml) were added under nitrogenatmosphere, cooled to -20 C. with dry ice acetonebath, added nButyllithium(460 mL, 1.15 mol, 2.5M, Energy Chemical) dropwise slowly,stirred at -10 C. for 2 h. N-methyl-N-methoxyacetamide(186 g, 1.44 mol) was added and stirred at room temperature overnight. The reactionmixture was quenched with a saturated ammonium chloride solution (1000 mL), the organic phase was collected, washed with water (1000mL×2), brine (1000 mL×2), dried over anhydrous sodium sulfate and concentrated under vacuum to obtain cyclopropyl-(3-methoxy-2-tetrahydropyran-2-yloxy-phenyl)methanone (8C) as a red liquid (280 g, crude product), which was submitted to the next step without furtherpurification

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; Sichuan Haisco Pharmaceutical Co., Ltd; Chin, Rinrin; Li, Fang chiong; Lee, Swi Swi; Luo, Huadong; Luo, Sin Pong; Wan, songrin; Ron, Ray; Liu, Guoliang; Wei, Yonggang; Liu, Chien Wi; Tang, Peongcho; (148 pag.)KR2016/5361; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 7150-72-3, name is tert-Butyl vinylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl vinylcarbamate

General procedure: A 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

The synthetic route of 7150-72-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5900-59-4, name is 2-Amino-4-chlorobenzamide, 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 5900-59-4, Safety of 2-Amino-4-chlorobenzamide

[00394] Step B: To a solution of 2-amino-4-chlorobenzamide (393 mg, 2.30 mmol) and DIEA (0.60 mL, 3.45 mmol) in THF (15 mL) at 0 0C was added ethyl chlorooxoacetate (0.28 mL, 2.53 mmol). The solution was allowed to warm to rt and stir for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate as a solid (545 mg, 88percent). 1H NMR (300 MHz, DMSO-d6) delta 1.32 (t, J= 6.97 Hz, 3 H), 4.31 (q, J= 6.97 Hz, 2 H), 7.34 (d, J= 8.48 Hz, 1 H), 7.86 – 8.03 (m, 2 H), 8.44 (br s, 1 H), 8.62 (s, 1 H), 13.24 (s, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-chlorobenzamide, and friends who are interested can also refer to it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics