Tag: M.W=100-200

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. 64214-66-0, name is 4-Chloro-N-methoxy-N-methylbutanamide, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Chloro-N-methoxy-N-methylbutanamide

Step B 3-Chloropropyl 3,5-dimethylphenyl ketone A solution of 10.2 mL (13.9 g; 72 mmol) 5-bromo-m-xylene in 200 mL of anhydrous tetrahydrofuran was stirred under nitrogen at -78 C. as 35.8 mL (84 mmol) of 2.5 M n-butyllithium in tetrahydrofuran was added dropwise. After 15 minutes at -78 C., a solution of 10.0 g (60 mmol) of 4-chloro-N-methoxy-N-methylbutyramide in 30 mL of anhydrous tetrahydrofuran was added dropwise over 25-30 minutes. The resulting solution was maintained at -78 C. for 45 minutes and then warmed briefly to room temperature. The reaction was quenched by addition of 40 mL of 2 N hydrochloric acid and then partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and then saturated aqueous sodium chloride solution. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue afforded 8.91 g (70%) of an oil, which had satisfactory purity by 1 H NMR (CDCl3).

According to the analysis of related databases, 64214-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US5985901; (1999); A;,
Amide – Wikipedia,
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108-13-4, name is Malonamide, 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. name: Malonamide

B-1. 1,2-Dihydro-5-(4-methoxyphenyl)-2-oxonicotinamide–A mixture containing 82.1 g. of 3-dimethylamino-2-(4-methoxyphenyl)-2-propenal, 63.15 g. of malonamide (97%), 54.0 g. of sodium methoxide and 800 ml. of methanol was refluxed with stirring for about 17 hours and chilled. The reaction mixture was filtered and the filtrate concentrated in vacuo to a volume of about 500 ml., acidified with acetic acid and chilled. The resulting solid was collected, dried at 90 C. in a vacuum oven to yield 25.25 g. of 1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinamide, m.p. 283-286 C.

The synthetic route of 108-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sterling Drug Inc.; US4515797; (1985); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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, category: amides-buliding-blocks

To a solution of (5S,7S)-2-bromo-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazole (150 mg, 0.47 mmol), N-methoxy-N-methyl-cyclopropanecarboxamide (122 mg, 0.94 mmol) in tetrahydrofuran (3 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 0.47 mL, 0.94mmol) dropwise at 0 C. After addition, the mixture was stirred at 0 C for 0.5 h and quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by RP-HPLC (acetonitrile 40-70%o / 0.225%o formic acid in water) to afford arbitrarily assigned cyclopropyl-[(5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H- pyrrolo[l,2-b] [l,2,4]triazol-2-yl]methanone (49.1 mg, 34%) as a white solid. lR NMR (400 MHz, CDCl3) delta 7.22 – 7.16 (m, 1H), 7.14 – 7.08 (m, 1H), 6.75 – 6.72 (m, 1H), 6.13 – 6.10 (m, 0.5H), 5.99 – 5.96 (m, 0.5H), 5.88 – 5.84 (m, 1H), 3.74 – 3.67 (m, 1H), 3.09 – 3.04 (m, 1H), 2.99 – 2.92 (m, 1H), 1.36 – 1.31 (m, 2H), 1.14 – 1.09 (m, 2H). LC-MS RT = 0.666 min, m/z = 308.1 [M+H]+. LCMS (5 to 95%o acetonitrile in water + 0.03 %> trifluoacetic acid over 1.5 mins) retention time 0.666 min, ESI+ found [M+H] = 308.1.

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, N-Methoxy-N-methylcyclopropanecarboxamide, other downstream synthetic routes, hurry up and to see.

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;,
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Electric Literature of 90-16-4, A common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, molecular formula is C7H5N3O, 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: Intermediates 3a-h were prepared by the similar method described in the literature [2] (Scheme 1). A stirring mixture of 2 (8 mmol), 1,3-dibromopropane (4.1 mL, 40 mmol) and potassium carbonate (2.208 g, 16 mmol) in acetone (200 mL) was heated to reflux and monitored by TLC. After the complete consumption of 2, the solvent was removed under reduced pressure. Then the residue was taken up in water and extracted with CH2Cl2 (80 mL ×3). The combined organic layer wasdried over anhydrous Na2SO4, concentrated and purified by flash column chromatography on silica gel using petroleum ether (60-90 C)/EtOAc (4:1) as eluent to yield 3. Intermediates 4a-h were prepared by the same method as above, using 1,4-dibromobutane instead of 1,3-dibromopropane.

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:
Article; Wang, Gao-Lei; Chen, Xi; Chang, Ya-Ning; Du, Dan; Li, Zhong; Xu, Xiao-Yong; Chinese Chemical Letters; vol. 26; 12; (2015); p. 1502 – 1506;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 112257-19-9, These common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

tert-Butyl N-methyl-N-(2-methylaminoethyl)carbamate (Intermediate 173, 300 mg, 1.59 mmol) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-indol-3-yl)pyrimidin-2-amine (Intermediate 129, 522 mg, 1.33 mmol) and DIPEA (0.462 mL, 2.65 mmol) in DMA (5 mL). The mixture was heated in a microwave at 100C for 4h. The mixture was then diluted with EtOAc and washed with water (5x), brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-2% CH3OH in CH2Cl2 gave the title compound (431 mg, 58%) as an orange solid after trituration with diethyl ether; 1H NMR: 1.37 (9H, s), 2.79 (3H, s), 2.88 (3H, s), 3.29-3.36 (2H, m), 3.39-3.44 (2H, m), 3.89 (3H, s), 3.99 (3H, s), 6.85 (1H, d), 7.14 (1H, t), 7.21-7.28 (2H, m), 7.53 (1H, br d), 8.04 (1H, s), 8.31-8.38 (3H, m), 8.72 (1H, br s); m/z: ES+ MH+ 562.35.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; FINLAY, Maurice, Raymond, Verschoyle; WARD, Richard, Andrew; KADAMBAR, Vasantha, Krishna; CHANDRASHEKAR, Reddy, C.; MURUGAN, Andiappan; REDFEARN, Heather, Marie; WO2013/14448; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application 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.

A solution of compound 1-1 (0.52 g, 2.3 mmol), 2-(lH-7-azabenzotriazol-l-yl)- 1,1 ,3,3-tetramethyl uronium hexafluoro -phosphate methanaminium (HATU, 1.74 g, 4.6 mmol), and 4-dimethylaminopyridine (1.39 g, 1 1.6 mmol) in CH2CI2 (40 mL) was stirred at room temperature for 1 hour, followed by slow addition ofcyclopropanesulfonamide (0.57 g, 4.7 mmol), diisopropylethylamine (1.81 mL, 14.0 mmol), and l ,8-diazabicyclo[5,4,0]undec-7-ene (1.80 g, 11.7 mmol) over15 minutes. After the reaction mixture was stirred at room temperature overnight, the solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give compound 1-2 (0.51 g, 66percent). MS m/z 353.1 (M++23); !H NMR (CDCI3) d 9.75 (brs, 1H), 5.64-5.51 (m, 1H), 5.30 (d, J = 17.4 H), 5.16 (d, J = 10.2 Hz, 1H), 2.95-2.89 (m, 1H), 2.19-2.10 (m, 1H), 1.93-1.88 (m, 1H), 1.47 (s, 9H), 1.46-1.38 (m, 1H), 1.32-1.23 (m, 2H), 1.15-1.00 (m, 2H).

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

Reference:
Patent; TAIGEN BIOTECHNOLOGY CO., LTD.; LIU, Chen-Fu; LEE, Kuang-Yuan; CHENG, Pei-Chin; LIU, Yo-Chin; LO, Pin; TSENG, Kuo-Feng; CHEN, Chih-Ming; KING, Chi-Hsin Richard; LIN, Chu-Chung; WO2011/34518; (2011); 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. 108-13-4, name is Malonamide, A new synthetic method of this compound is introduced below., Formula: C3H6N2O2

[0533] Into a 3000-mL 3-necked round-bottom flask were placed a solution of sodium ethoxide (155 g, 2.28mol, 4.00 equiv) in ethanol (2000 mL), malonamide (233 g, 2.28mol, 4.00 equiv) and 5-chloro-l,3-dimethylpyrimidine-2,4(lH,3H)-dione (100 g, 571.43 mmol, 1.00 equiv). The resulting solution was heated to reflux for 20 min. Then it was cooled and concentrated under vacuum. The residue was diluted with 500 mL of H20, and then adjusted to pH 2 with HCl. The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 50 g (crude) of 5-chloro-2,6-dihydroxynicotinamide as a white solid.

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; ANACOR PHARMACEUTICALS, INC; JARNAGIN, Kurt; AKAMA, Tsutomu; WO2011/94450; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 154748-63-7, These common heterocyclic compound, 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, 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 a solution of tert-butyl (3 -hydroxycyclobutyl)carbamate (see PREPARATION 4B; 1.08 g, 3.8 mmol) in DMF (20 mL) at RT was added sodium hydride (60% wt in mineral oil) (0.18 g, 7.6 mmol). The mixture was stirred at RT for 10 min and then 3-Bromo-2-fluoro- pyridine (665 mg, 3.8 mmol) was added. The reaction mixture was stirred at RT for lh and then diluted with water (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2S04, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash columnchromatography on silica gel (5% to 30%> EtOAc in hexanes) to give tert-butyl ((lS,3S)-3-((3- bromopyridin-2-yl)oxy)cyclobutyl)carbamate (391 mg, 1.14 mmol, 30%> yield ) as white solid. ESI-MS (M+l): 343 calc. for Ci4Hi9BrN203 342.

Statistics shows that tert-Butyl (3-hydroxycyclobutyl)carbamate is playing an increasingly important role. we look forward to future research findings about 154748-63-7.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); 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. 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

To a solution of 1-aminocyclopentane-1-carboxamide (1.00 g, 7.80 mmol) in DCM (16 mL) was added TEA (2.72 mL, 19.50 mmol). The mixture was cooled to 0 C with an ice bath. Propionyl chloride (1.011 g, 10.92 mmol) in DCM (4 mL) was added dropwise to the stirred solution, and the reaction mixture was at RT for 18 hours. The reaction was diluted with 0 and DCM. The organic phase was collected. The aqueous phase was extracted (2X) with DCM. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give Intermediate 112a (0.586 g, 3.18 mmol, 40.8 % yield) as a solid. LC-MS (Method A2) RT =0.46 min, MS (ESI) m/z: 185.1 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 9.37 – 9.15 (m, 2H), 8.71 (br d, J=0.9 Hz, 1H), 2.42 (q, J=7.4 Hz, 2H), 2.39 – 2.29 (m, 2H), 1.85 – 1.68 (m, 4H), 1.67 – 1.58 (m, 2H), 1.14 – 1.10 (m, 3H).

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 17193-28-1.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H18N2O2

Example 5 : Synthesis of compounds 7 and 80.17 g (1.5 mmol) N-methylpiperid-4-one and 0.178 g (1.0 mmol) N-Boc-N-methyl-1,2- diaminoethane were reacted with 0.42 g (2.0 mmol) sodium triacetoxyborohydride in 5 ml DCE at RT overnight. The reaction was quenched with MeOH and the mixture extracted with DCM and brine (basified to pH > 12), dried with MgS04 and concentrated in vacuo to give 0.31 g (100%) of 7 as an oil. 1H-NMR (300MHz, CDC13): delta = 1H-NMR (300MHz, CDC13): delta = 1.38 (2, m, CH2), 1.45 (9H, s, Boc), 1.76 (1H, br s, NH), 1.85 (2H, m, CH2), 2.00 (2H, m, CH2), 2.27 (3H, s, MeN), 2.46 (1H, m, CH), 2.76 (4H, m, 2xCH2), 2.86 (3H, s, MeN), 3.30 (2H, t, CH2); MS (ESI) m/z = 272.2 +H+).

The synthetic route of 121492-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTARGA B.V.; BEUSKER, Patrick, Henry; COUMANS, Rudy, Gerardus, Elisabeth; ELGERSMA, Ronald, Christiaan; MENGE, Wiro, Michael, Petrus, Bernardus; JOOSTEN, Johannes, Albertus, Frederikus; SPIJKER, Henri, Johannes; DE GROOT, Franciscus, Marinus, Hendrikus; WO2011/133039; (2011); A2;,
Amide – Wikipedia,
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