Tag: M.W=100-200

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;,
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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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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;,
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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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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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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;,
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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. 84713-20-2, name is Benzyl vinylcarbamate, A new synthetic method of this compound is introduced below., Computed Properties of C10H11NO2

Aniline (3.64 mL, 39.97 mmol, 1.0 equ) was dissolved in methylene chloride (100 mL) and Na2S04 (2 g) was added and cooled to-25 C. Acetaldehyde (2.23 mL, 39.97 mmol, 1.0 equ.) was added to the solution and stirred for Ih at-25 C. Sodium sulfate was filtered off and N-vinyl- carbamic acid benzyl ester (7.07g, 39.97 mmol, 1.0 equiv) was added to the filtrate at-25C, followed by boron triflouride diethyl etherate (0.50 mL, 3.9 mmol, 0.1 equ). The reaction was allowed to stir at -25C for Ih and then warmed to room temperature and stirred for lOh. The reaction was evaporated in vacuo and the residue was purified by Biotage flash system (20% ethyl acetate/80% hexane) to yield 4.0 g, 33 % of (No.)-cis-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester as a white solid. H’ NMR (300 MHz, CDC13) &:7.38 (m, 5H), 7.17 (d, 1H), 7.02 (t, IH, C7-H), 6.68 (t, IH), 6.47 (d, IH), 5.17 (bs, 2H), 5.07 (m, IH), 4.92 (d, 1H), 3.57 (m, IH), 2.30 (m, IH), 1.47 (q, IH), 1.21 (d, 3H).

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; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/100321; (2005); A1;,
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Reference of 149632-73-5, 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 149632-73-5 as follows.

Under a nitrogen atmosphere, a solution of 3,6-difluoro-9-(oxiran-2-ylmethyl)-9H-carbazole(0.7 g) andtert-butyl (1-aminopropan-2-yl)carbamate(1.5 g) in ethanol (50 mL) was stirred at 70C for 16 hrs. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography, eluting with a gradient of 0-20% methanol in dichloromethane to give an off-white foam (1.28 g). The product was used directly in the next step without additional purification:1H NMR (300 MHz, CDCl3): delta 7.67 (dd, 2H,J= 8.7, 2.7 Hz), 7.42-7.37 (m, 2H), 7.22 (td, 2H,J= 9.0, 2.7 Hz), 4.55-4.30 (m, 3H), 4.13 (m, 1H), 3.78 (br s, 1H), 2.88 and 2.82 (dd, 1H,J= 12.0, 3.6 Hz), 2.70-2.50 (m, 3H), 1.45 (s, 9H), 1.13 and 1.11 (d, 3H,J= 6.6 Hz). ESI (m/z): 434.0 (M+H).

According to the analysis of related databases, 149632-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Humphries, Paul S.; Bersot, Ross; Kincaid, John; Mabery, Eric; McCluskie, Kerryn; Park, Timothy; Renner, Travis; Riegler, Erin; Steinfeld, Tod; Turtle, Eric D.; Wei, Zhi-Liang; Willis, Erik; Bioorganic and Medicinal Chemistry Letters; vol. 28; 3; (2018); p. 293 – 297;,
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Electric Literature of 112257-19-9,Some common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

To a solution of Compound 79-4a (510 mg, 1.57 mmol) in DCE (5 mL) at 25¡ã C. was added tert-butyl N-methyl-N-[2-(methylamino)ethyl]carbamate (300 mg, 1.59 mmol, 1.01 eq). The mixture was stirred for 1 h, AcOH (52.50 mg, 0.874 mmol, 0.0556 eq) and NaBH(OAc)3 (666.47 mg, 3.14 mmol, 2 eq) were added and the mixture was stirred at RT for 3 hr, then partitioned between saturated aq. NaHCO3 (50 mL) and EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound (0.77 g, 1.38 mmol, 88percent yield) as yellow oil. MS (ES+) C26H42F2N4O3, requires: 496, found: 497 [M+H]+.

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; MCAFOOS, Timothy Joseph; (166 pag.)US2019/270739; (2019); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, 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 19047-31-5, Computed Properties of C5H8ClNO

General procedure: To a solution of 5- bromine -2- chlorophenol (2.9g, 14.3mmol) in 50mL acetonitrile was added K2CO3 (2.5g,17.1mmol), and stirred for 30min intermediate product 10 was added and the solution was heated to 80C for 4h. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with water and brine for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 11.

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, 2-Chloro-N-cyclopropylacetamide, other downstream synthetic routes, hurry up and to see.

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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