Month: March 2021

Reference of 108-13-4,Some common heterocyclic compound, 108-13-4, name is Malonamide, molecular formula is C3H6N2O2, 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.

Step A:; To a solution of anyhydrous methanol (50 mL), sodium methoxide/methanol solution (61.47 mmol) and malonamide (4.50 g, 44.08 mmol) was added (E)-4-ethoxy-l,l,l-trifluoro-3-butene-2-one V-I (7.781 g, 46.28 mmol) and the mixture was heated to reflux for 2 hours. When the reaction was quenched by addition of water and the aqueous layer pH was adjusted to pH 1-3 with HCl. The mixture was concentrated to give compund V-2 (m/z (ES) (M+H)+= 207), which was used in the next step without further purification.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/41052; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 96-30-0,Some common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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.

The preparation mother liquid (129 mL) of O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorothioate in Example 1 which had been reused 6 times was added with methanol to 130 ml. Add 32.82 g (0.2 mol) of the sodium O,O-dimethylthiophosphate prepared in the step (2), 21.5 g (0.2 mol) of 2-chloro-N-methylacetamide prepared in the step (1) and 1.66 g (0.01 mol) of potassium iodide were reacted at 65 C for 10 hours, and then the heating was stopped. After naturally dropping to room temperature, the salt formed by the reaction is filtered off, Rotating to remove the solvent, That is, 40.98 g of light yellow O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorothioate was obtained, the yield was 96.1%; The purity by GC was 95.22%; the water content of the product was 0.044%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-N-methylacetamide, its application will become more common.

Reference:
Patent; Henan Chemical Institute Co., Ltd.; Huo Erfu; Cheng Weiqin; Feng Ming; Wang Bonan; Wang Yanhua; Chang Shuhao; Dong Guangxia; Yang Shuai; Wang Yinan; (16 pag.)CN109651432; (2019); A;,
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Related Products of 24036-52-0, A common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, 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.

General procedure: To a solution of 5 (350mg, 1.54mmol) in 20mL THF was added phenylboronic acid (3.28mmol), copper acetate (420mg, 2.31mmol), Et3N (0.5mL, 4.62mmol) and 4A molecular sieve (50mg). The solution was stirred at 60C for 6h. After the completion of the reaction (monitored by TLC), the reaction solution was concentrated, and added with 20mL water. The reaction was filtered to remove solids and extracted with EtOAc, the organic layer was collected and washed with saturated salt solution for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford target product.

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
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Reference of 6331-71-1, 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. 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

[00258] Compound 38 [00259] [00261] [00262] To a mixture of 4-chloro-6-((4,7-difluoro-2-methyl-lH-indol-5- yl)oxy)pyrimidine-5-carbonitrile (80 mg, 0.25 mmol) and 4-amino-N,N-dimethylbenzamide (49 mg, 0.30 mmol) in anhydrous DMSO (1.5 mL) was added TEA (0.122 mL; 0.875 mmol), and the resulting biphasic mixture was efficiently stirred at room temperature for ca. 3 days. The resulting mixture was diluted with EtOAc (100 mL) and washed with aq. NaHC03 (ca. 100 mL each; 50% NaHC03 saturation). The organic layer was separated and dried over anhydrous Na2S04 and concentrated. The resulting residue was purified by crystallization (DCM) to afford the desired product as a white solid (49 mg, 44% yield). 1H NMR (DMSO- d6, 400 MHz) delta 11.85 (br s, 1H), 10.20 (br s, 1H), 8.33 (s, 1H), 7.60 (d, J = 8.4 Hz, 2H), 7.41 (d, J = 8.4 Hz, 2H), 7.04-7.00 (m, 1H), 6.35 (s, 1H), 2.97 (s, 6H), 2.42 (s, 3H); MS (ESI): calcd for C23H18F2N602: 448, found: 449 (MH+).

The chemical industry reduces the impact on the environment during synthesis 4-Amino-N,N-dimethylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
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Reference of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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.

General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2¡¤H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. An anhydrous toluene (1.0 mL) solution of ethyl diazoacetate 4a (30 muL, 0.30 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane=1:2) to give isoindolinone 3i in 80% yield.

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
Amide – Wikipedia,
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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 3984-14-3 as follows. HPLC of Formula: C2H8N2O2S

2-(1H-indoi-6-yl)-3-[4-(tetrahvdro-pyran-4-yioxymethyi)-phenyiethynvi-benzoic acid (45.1 rng, 0.1 mrnol) and dimethylsulfarnoyl amine (149 mg, 0.14 rnrnoi) were dissolved in N,Ndimethyiforinarnide (1 mL), followed by the addition of 1-ethyl-3-(3-dimethyiaminopropyl)carbodiimide hydrochloride (1.2 eq), 4-dimethylarninopyii dine (2 eq) and hydroxybenzotriazole (1.2 eq). The reaction was stirred at room temperature for 16 hours. The solvent was then evaporated to dryness and reaction mixture was purified by preparative HPLC to give product as an off-white solid in 68% yield. ?H NMR (300 MHz, CDCI3) d ppm 8.39 (hr. s., I H) 7.71-7.86 (in, 3 Fl) 7.54 (s, I H) 7.39-7.51 (m, 2 H) 7.20-733 (m, 4 H) 716 (d, .J=7.92 Hz, 2 H) 7.01 (d, J=8.21 Hz, 2 H) 6.63 (br. s.,1 H) 4.49 (s, 2 H) 3.88-4.06 (m, 2 H) 3.37-3.61 (in, 3 H) 2.56 (s, 6 H) 1.82-1.99 (m, 2 H) 1.54-1.75 (in. 2 H,). MS m/z (M-i-H) 558.2.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE WISTAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy E.; SMITH, Garry R.; REITZ, Allen B.; LIEBERMAN, Paul M.; MCDONNELL, Mark E.; ZHANG, Yan; CARLSEN, Marianne; CHEN, Shuai; (205 pag.)WO2016/183534; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 389890-42-0, 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. 389890-42-0, name is tert-Butyl (trans-3-hydroxycyclobutyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 26-b To a solution of intermediate 8-b (2.0 g, 10.7 mmol) in anhydrous THF (53 ml) cooled to 0C was slowly added a 1.0 M solution of LiAIH4 in THF (32.0 ml, 31.0 mmol). After the addition was completed, the reaction was warmed to room temperature, stirred at 65C for 2 hours and then cooled to 0C. 15% aqueous NaOH was then added and after stirring for 15 minutes the reaction was filtered. The filtrate was concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 26-b as a white solid.

The synthetic route of tert-Butyl (trans-3-hydroxycyclobutyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; MORRIS, Stephen J.; (184 pag.)WO2016/187723; (2016); A1;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 150349-36-3,Some common heterocyclic compound, 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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.

l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3-Amino-propyl)-methyl-carbamic acid tert- butyl ester (2.25 g, 11.9 mmol) and diisopropylethylamine (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- pheny]amino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0. Preparation #9 [3-(2-chloro-6-nitro-phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3 -Amino-propyl )-methyl-carbamic ac id tert-butyl ester (2.25 g, 11.9 mmol) and diisopropylethylami?e (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (JSIa2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0- To a solution of the above nitro aniline in acetic acid (53 mL) at room temperature was added iron powder (1.2 g, 21.2 mmol). After stirring for about 15 hours the reaction mixture was filtered and concentrated in vacuo. The crude product was dissolved in diethyl ether and washed with a solution of 2N NaOH that had been saturated with EDTA. The organic layer was further washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to provide [3-(2-Amino-6-chloro-rhohenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil that was used in subsequent reactions without further purification. RP-HPLC R, 6.05 min. (table 1, method a). To a solution of the crude phenylene diamine in EtOH (98 mL) was added NaOAc (1.8 g, 22 mmol) followed by a 5 N solution of cyanogen bromide in acetonile (1.4 mL, 7.2 mmol). After stirring for about 20 hours at room temperature the reaction mixture was concentrated in vacuo. The crude reaction mixture was diluted with Et2O (200 mL) and 2 N NaOH (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography on silica gel (gradient elution 5-10% MeOH/CH2Cl2, containing 1% Et3N) to provide 1.3 g of [3-(7-Chloro-2- imino-2,3-dihydro-ben2oimJdazol-l-yl)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil. RP-HPLC R, 6.05 min (table 1, method a), m/z: (M+H)+ 339.0, 341.1 (3:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(N-Boc-N-methylamino)propylamine, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/84728; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, 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. Application In Synthesis of 5-Amino-2-methylbenzenesulfonamide

To a stirred suspension of the product of Intermediate Example 4 (1 .1 g, 3.7 mmol) in 10 mL of THF, was added 5-amino-2-methylbenzenesulfonamide (0.70 g, 3.8 mmol, 1 .0 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 0.072 mmol) was added in one portion. After 5 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 16 mL of THF and dried in the air to yield 1 .6 g (92%) of 5-({4-[(2,3- dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methylbenzene sulfonamide monohydrochloride as a light yellow solid.

The synthetic route of 6973-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); 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. 131818-17-2, name is tert-Butyl (4-bromophenyl)carbamate, A new synthetic method of this compound is introduced below., Product Details of 131818-17-2

b) tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).

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; Abbott Laboratories; US6921763; (2005); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics