Category: amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, 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 147356-78-3, COA of Formula: C6H11NO2

To a solution of N-methoxy-N-methyl-cyclopropanecarboxamide (1.2 g, 9.10 mmol) and [cis-2- bromo-7-deuterio-5-phenyl-5,6-dihydropyrrolo[l,2-b][l ,2,4]triazol-7-yl]oxy-tert-butyl-dimethyl- silane (1.8 g, 4.55 mmol) in tetrahydrofuran (40 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 6.83 mL, 13.66 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h and quenched by addition of saturated aqueous ammonium chloride (50 mL). The mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 – 200 mesh, 0 to 20% ethyl acetate in petroleum ether) to give [cis-7-[tert- butyl(dimethyl)silyl]oxy-7-deuterio-5-phenyl-5,6-dihydropyrrolo[l,2-b] [l,2,4] triazol-2-yl]- cyclopropyl-methanone (450 mg, 26%>) as a colorless oil. LCMS RT = 1.030 min, m/z = 384.2 [M + H]+. LCMS (5 to 95%> acetonitrile in water + 0.03 %> trifluoacetic acid over 1.5 mins) retention time 1.030 min, ESI+ found [M+H] = 384.2.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 94838-59-2,Some common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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 mixture of dihydro-2//-thiopyran-4(3//)-onc (0.488 g, 4.2 mmol), tert- butyl 4- aminophenethylcarbamate (0.5 g, 2.1 mmol) and ZnCh (0.859 g, 6.3 mmol) in methanol (10 mL) was stirred at room temperature overnight. After this time NaBHiCN (0.66 g, 10.5 mmol) was added and the mixture was heated at 40 C for 4 h. After it was cooled to room temperature, the reaction mixture was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by column chromatography to afford the title compound as light-yellow solid (0.401 g, 56.7% yield). NMR (500 MHz, DMSO-r/d) d: 6.87 (d, J= 8.3 Hz, 2H), 6.79 (t, J = 5.3 Hz, 1H), 6.50 (d, J= 8.4 Hz, 2H), 5.31 (d, .7= 8.6 Hz, 1H), 3.26 – 3.19 (m, 1H), 3.03 (dd, J= 14.6, 6.3 Hz, 2H), 2.68 (dd, J= 9.6, 3.4 Hz, 4H), 2.52 (d, J= 9.6 Hz, 2H), 2.20 – 2.09 (m, 2H), 1.47 (ddd, J= 13.4, 9.7, 4.7 Hz, 2H), 1.37 (s, 9H).

The synthetic route of 94838-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); 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. 614-76-6, name is 2-BroMoacetanilide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 614-76-6

2-Bromoacetanilide (1 .68 g, 90% content, 7.06 mmol) is dissolved in dry THF (15 mL) and cooled to -78 C under a nitrogen atmosphere. n-Butyllithium (2.5 M solution in hexane, 5.93 mL, 14.8 mmol) is added dropwise and the mixture stirred at -78 C for 30 minutes. tert-Butyl 2-formylpropan-2-ylcarbamate (1 .39 g, 7.42 mmol) in dry THF (10 mL) is added dropwise and the mixture stirred for 30 minutes at -78 C then allowed to warm to -50 C over 1 hour. Saturated aqueous ammonium chloride solution (20 mL) is added, the mixture allowed to warm to room temperature and the phases separated. The organic phase is washed with brine, dried and the solvent removed. The residue is purified by flash chromatography (Eluent 0-2% MeOH in DCM) to give the title product (370 mg, 16%). UPLC-MS (Method 1 ): Rt = 1 .02 min MS (ESI+): m/z = 323 (M+H)+

According to the analysis of related databases, 614-76-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAZZAFERRO, Rocco; FERRARA, Marco; GIOVANNINI, Riccardo; LINGARD, Iain; (195 pag.)WO2016/75239; (2016); 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. 88-19-7, name is 2-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H9NO2S

{3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester (7 kg), dimethyl amino pyridine (2.5 kg), dicyclohexyl carbodiimide (3.9 kg), and dichloromethane (70 L) are charged and stirred for about 15 minutes. O-toluene sulphonamide (3.4 kg) is added at 30 C. and the reaction solution is stirred for about 4 hours at 30 C. The unwanted separated solid is filtered and the reaction solution is washed with dichloromethane (2¡Á12 L). The obtained organic layer is washed with dilute hydrochloric acid and water and separated. The obtained organic solution is distilled off completely under vacuum below 45 C. Acetonitrile (14 L) is added and distilled off completely under vacuum. The obtained crude is cooled to 30 C., acetonitrile (35 L) is added and heated to 85 C., and stirred for about 40 minutes. The resultant reaction solution is cooled to 35 C. and stirred for about 55 minutes. The separated solid is filtered, washed with acetonitrile (7 mL), and suction dried for about 30 minutes. The obtained wet compound is again charged into a reactor containing methanol (84 L), heated to about 60 C., and stirred for about 30 minutes. The reaction solution is cooled to 30 C. and stirred for about 50 minutes for solid separation. The obtained solid is filtered, washed with methanol (7 L), and suction dried for 30 minutes. The solid is dried under vacuum at 70 C. for about 4 hours to afford the title compound.HPLC Purity: 97.5%

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; Anumula, Raghupathi Reddy; Gilla, Goverdhan; Alla, Sampath; Kurella, Sreenivasulu; Kopparapu, Janardana Sarma Ramachandra; Medisetti, Rama Krishna Venkata; Maddula, Srinivasula Reddy; US2009/149662; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39549-79-6, its application will become more common.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 14719-21-2, 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 14719-21-2 as follows.

F1 (0.7 mmol, 247 mg) was added to a single-necked flask and 9.7 mg CuI and 20.3 mg Pd (PPh3) 4 (tetrakistriphenylphosphine) palladium were weighed into a reaction flask. The reaction flask was evacuated, purged with nitrogen and wrapped in aluminum foil , 2.3 ml DMF was added,Stirring to dissolve, adding 0.2ml TEA, weighing F2 (254mg, 1.7mmol) dissolved in DMF was added to the above reaction flask, stirred at room temperature, the reaction overnight.TLC plate monitoring, EA as developing solvent, Rf = 0.35 as the raw material F1, Rf = 0.32 for the product F3, two very close position.After the reaction was over, the solvent was evaporated to dryness under reduced pressure and the residue was directly purified by column chromatography. Elution with 20: 1 DCM: MeOH as eluant gave 214 mg, yield 61%.

According to the analysis of related databases, 14719-21-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Gong Bing; Shao Zhifeng; Zhao Xiaodong; Liu Yazhi; Li Xiaowei; Wu Xinyan; Wei Xiaofei; Tang Daonian; (99 pag.)CN104292117; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 14062-80-7,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.

N’-cyanobenzimidamide (16.8 g, 115 mmol),Compound A-2 (21 g, 115 mmol) and phosphorous oxychloride(12 mL, 128 mmol) was added to 500 mL of acetonitrile, followed by stirring and refluxing for 1 hour.After cooling to room temperature, the resulting solid was filtered,Washed with water and ethanol, and then dried to obtain CompoundA (27.6 g, yield 80%).

The synthetic route of 14062-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Kang Min-yeong; Park Tae-yun; Cho Seong-mi; Moon Jeong-uk; Jeong Min-u; Lee Jeong-ha; (29 pag.)KR2019/6353; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 111300-06-2,Some common heterocyclic compound, 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, 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 frans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}- formamide in anhydrous THF at 0C may be treated with borane-THF complex in THF (1 M, excess). The reaction may be allowed to come to room temperature and may be monitored by LCMS until the reaction is complete. The reaction may be quenched with MeOH and the solvents may be removed under reduced pressure. The crude product may be purified by flash chromatography using with 1 – 5 % (2N N H3 in MeOH) in DCM to give frans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]- cyclohexyl}-methyl-amine. The neutral amine may be treated with 2N HCI in diethyl ether and DCM.The volatiles may be removed under reduced pressure and the salt may be triturated with diethyl ether and filtered to provide the title compound. LCMS: m/z 439 [M + 1].

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 (trans-4-hydroxycyclohexyl)carbamate, its application will become more common.

Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
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 185693-02-1 as follows. Safety of tert-Butyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

To R20 (6.0 g, 28.26 mmol) in dichioromethane (200 mL) are added R21 (3.16 mL, 31.09 mmol) and acetic acid (1.62 mL, 28.26 mmol) and stirred for 1 h at r.t.. Sodiumtriacetoxyborohydride (9.46 g, 42.40 mmol) is added and stirred overnight at r.t.. The reaction mixture is diluted with dichloromethane and saturated sodium hydrogencarbonate solution. The organic layer is dried and concentrated in vacuo.Yield 100% m/z 303 [M+H]+, rt 1.34 mi LC-MS Method VOll SOl.

According to the analysis of related databases, 185693-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; BIXENMANN, Achim; GRUNDL, Marc; HAEBEL, Peter Wilhelm; PAUTSCH, Alexander; (80 pag.)WO2016/16242; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 120157-96-2, 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. 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a cold suspension of LiAlH4 (60 mg, 1.5 mmol) in ether (5 mL) at -78 C. was added dropwise a solution of methyl 4-(N-t-Boc-aminomethyl)benzoate (0.8 g, 3 mmol) in ether (5 mL) and the contents were allowed to warm-up to ambient temp. After 3 h, further amount of LiAlH4 (100 mg) was added and the reaction was continued at room temp for further 10 min. Excess LiAlH4 was destroyed with EtOAc followed by saturated ammonium chloride (1.0 mL), The solid precipitated was filtered and washed with ether. The filtrate was evaporated to give 4-(N-t-Boc-aminomethyl)benzyl alcohol (250 mg, 35%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics