Tag: M.W=200-300

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. 25823-52-3, name is 6,7-Dihydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3(5H)-one, A new synthetic method of this compound is introduced below., Computed Properties of C13H12N2O

A. A mixture of the compound of formula (De), 3-oxo-6,7-dihydro-5H- benzo[6,7]cyclohepta[1,2-c]pyridazine (4.0 g, 19.3 mmol) and POCI3 (20 ml.) was refluxed for 2 h. After cooling to ambient temperature, the volatiles were evaporated.The residue was poured into a mixture of ice water and sodium bicarbonate, CH2CI2 (200 ml.) was added to dissolve the solid. The layers were separated, and the aqueous layer was extracted with CH2CI2 one more time. The combined organic layers were washed with brine. After being dried (MgSO4), filtered, and concentrated, the compound of formula (Df), 3-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1 ,2-c]pyridazine was obtained as a yellow solid (4.3 g, 99%), 1H NMR (300 MHz, CDCI3) delta: 7.82 (m, 1 H), 7.45- 7.24 (m, 4H), 2.59-2.51 (m, 4H), 2.27 (quant, J = 6.9 Hz, 2H); LC-MS: purity: 100%; MS (m/e): 231 (MH+). B. Alternatively, 3-Oxo-6,7-dihydro-5/-/-benzo[6,7]cyclohepta[1 ,2-c]pyridazine was heated with 20 ml. of phosphorus (III) oxychloride at 100 0C for 4.75 h. The solvent was removed under vacuum. The residue was treated with ice and saturated sodium bicarbonate solution. The solid which formed was filtered off, washed well with water and air-dried to yield the corresponding 3-chloro-6,7-dihydro-5H- benzo[6,7]cyclohepta[1 ,2-c]pyridazine (1.6 g); 1H NMR (CDCI3, 300 MHz) 7.82 (m, 1 H), 7.44 (m, 2H), 7.39 (s, 1 H), 7.27 (m, 1 H), 2.55 (m, 4H), 2.32 (m, 2H) ppm; MS (ES) 231/233 (M+H).

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; RIGEL PHARMACEUTICALS, INC.; WO2008/83367; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 106984-09-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 106984-09-2 name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of tert-butyl N-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl]carbamate (3.0 g, 10.2 mmol) and triethylamine (2.07 g, 2.77 mL, 20.5 mmol) in DCM (30 mL) was added mesyl chloride (1.41 g, 12.3 mmol) at 0 C. The reaction mixture was stirred at rt for 17 h. On completion, the mixture was quenched with water (30 mL) and extracted with DCM (2×30 mL). The organic layer was washed with sat.NaHCO3 (40 mL), then washed with brine (40 mL), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (3.6 g, 95% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 5.05 (s, 1H), 4.43-4.39 (m, 2H), 3.82-3.78 (m, 2H), 3.71-3.69 (m, 2H), 3.69-3.67 (m, 2H), 3.67-3.62 (m, 4H), 3.56 (t, J=4.8 Hz, 2H), 3.34 (q, J=4.8 Hz, 2H), 3.10 (s, 3H), 1.46 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 71026-66-9, name is tert-Butyl (4-aminophenyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H16N2O2

To a solution of N-Boc-p-phenylendiamine (53.7 mg, 0.258 mmol) inMeOH (5 mL), paraformaldehyde (37.4 mg) and sodium methoxide(67.4 mg, 1.248 mmol). The mixture was stirred for 11 h at reflux underan inert atmosphere. Then, the reaction mixture was reacted withNaBH4 (14.5 mg, 0.383 mmol) at room temperature and refluxed for anadditional 4 h. The mixture was concentrated in vacuo. The residue wasdissolved in saturated aqueous NH4Cl, was extracted with ethyl acetateand dried over Na2SO4. The solvent was concentrated in vacuo and waspurified by column chromatography on silica gel with Hexane: ethylacetate (7:3) to give N?-Boc-N-methyl-p-phenylendiamine as a yellowoil (45.7 mg, 80%). N?-Boc-N-methyl-p-phenylendiamine was dissolvedin 4M HCl/dioxane (500 muL) and stirred at room temperature for 2 h.The solvent was concentrated in vacuo and was dissolved in DMF(1 mL). This solution was added D-desthiobiotin (45.1 mg, 0.210 mmol),EDCI-HCl (41.1 mg, 0.214 mmol), HOBt (28.2 mg, 0.209 mmol) andDIEA (103.4 muL, 0.6 mmol). The mixture was stirred at room temperaturefor 15 h and was concentrated in vacuo. The residue was dissolvedin saturated aqueous NaHCO3, was extracted with ethyl acetate anddried over Na2SO4. Then, the residue was purified by preparative thinlayer chromatography with CH2Cl2_MeOH=10:1 to give 16 as a whitesolid (15.1 mg, 24%). 1H NMR (500 MHz, CD3OD) delta 7.29 (d, J=8.9 Hz, 2H), 6.61 (d, J=8.9 Hz, 2H), 3.86-3.80 (m, 1H), 3.74-3.70(m, 1H), 3.37 (s, 1H), 2.76 (s, 3H), 2.35 (t, J=7.5 Hz, 2H), 1.73 (quint,J=7.4 Hz, 2H), 1.56-1.34 (m, 6H), 1.12 (d, J=6.5 Hz, 3H); 13C NMR(125 MHz, CD3OD) delta 172.8, 164.8, 147.1, 128.2, 121.9, 112.3, 56.0,51.3, 36.2, 29.7, 28.3, 28.9, 25.8, 25.5, 14.2; FT-IR (neat) 3242, 3140,3067, 2925, 2855, 1691, 1652, 1602, 1517, 1430, 1401, 1376, 1347,1306, 1249, 1176, 1155, 1101, 1062 cm-1; Mp 85-87 C ; HRMS (ESI,positive): m/z calcd. for C17H26N4O2 [M+Na]+: 341.1948, found341.1945

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 71026-66-9.

Reference:
Article; Sato, Shinichi; Yoshida, Masaki; Hatano, Kensuke; Matsumura, Masaki; Nakamura, Hiroyuki; Bioorganic and Medicinal Chemistry; vol. 27; 6; (2019); p. 1110 – 1118;,
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. 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, A new synthetic method of this compound is introduced below., Product Details of 19982-07-1

Example 5: Memantine hydrochloride synthesis; 486g (600 ml) of n-butanol, 150 g of l-acetamido-3,5-dimethyladamantane and241 g of 89.9% potassium hydroxide are added to a 2-liter reactor equipped with a condenser, a mechanical stirrer, and a thermometer at 20-250C under nitrogen. After addition, the internal temperature rises to 40-450C without external cooling. The resulting suspension is heated to 128-132C over 20-30min and a solution is obtained. After lOhrs at 128-132C (no reflux), the reaction is complete (unreacted l-acetamido-3,5- dimethyladamantane less than 1%).After cooling to 45-500C, water (450ml) is added to form a biphasic system. After stirring (5min) and standing (15min) at 20-250C, the phases are separated. The aqueous phase is discarded and water (225ml) is added to organic phase to form a biphasic system and pH is brought to 10.5-11 with 37% hydrochloric acid (1Og). After stirring (5min) and standing (15min) at 20-250C, the phases are separated. Water (225ml) is added to the organic phase to form a biphasic system and after stirring (5min) and standing (15min) at 20-250C, the phases are separated. To the organic phase, 37% hydrochloric acid (66,9g) is added and the solution is filtered on paper filter. The obtained solution is concentrated under vacuum until a residual volume of 360 ml is obtained (a semisolid but well stirrable mixture) and internal temperature is 5O-55C. At this point, after cooling to 45-500C, ethyl acetate (750ml) is added. The obtained suspension is cooled to 0+/-3C and after 3hrs it is filtered and solid washed three times with ethyl acetate (90ml each). Wet white solid is dried under vacuum at 55-600C for 15 hrs. Dry weight: 138.7g, Yield: 95%, Purity: 99.97% by GC.

The synthetic route of 19982-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL FINE CHEMICALS S.R.L.; TEVA PHARMACEUTICALS USA, INC.; WO2007/126886; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 79722-21-7, A common heterocyclic compound, 79722-21-7, name is tert-Butyl benzyloxycarbamate, molecular formula is C12H17NO3, 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.

Sodium hydride 60% dispersion in mineral oil (0.55 g, 13.7 mmol) was added portion- wise to a stirring solution of fe/f-Butyl /V-(benzyloxy)carbamate (2.05 g, 9.18 mmol) in DMF (15 mL) under a nitrogen atmosphere at ambient temperature. The reaction mixture was stirred for 15 min. 1 (3.00 g, 10.1 mmol) in DMF (10 mL) was added dropwise and the reaction mixture was stirred under a nitrogen atmosphere at ambient temperature overnight. The reaction mixture was quenched with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The organic layers were pooled, washed with brine (100 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 1 :4 ethyl acetate/hexane to give a yellow oil (Yield: 1 .94 g, 37%). (0296) 1 H NMR (400 MHz, CDCI3): : delta 7.78 – 7.82 (m, 2H), 7.65 – 7.70 (m, 2H), 7.29 – 7.37 (m, 5H), 4.77 (s, 2H), 3.87 (t, J = 7.2 Hz, 2H), 3.69 (t, J = 7.2 Hz, 2H), 3.60 – 3.62 (m, 2H), 3.54 – 3.57 (m, 2H), 1.45 (s, 9H); 13C NMR (101 MHz, CDCI3): delta 168.3, 156.8, 135.8, 134.1 , 132.3, 129.6, 128.6, 128.5, 123.4, 81 .5, 77.1 , 67.7, 67.3, 49.8, 37.5, 28.4.

The synthetic route of 79722-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; CODD, Rachel; KATSIFIS, Andrew; LIFA, Tulip; TIEU, William; RICHARDSON-SANCHEZ, Tomas; (90 pag.)WO2017/96430; (2017); 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. 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Example 10 (2S)-1-{[2-(5-Brom-2,3-dihydro-indol-1-yl)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile, Hydrochloride Salt This compound was made from 5-brom-2,3-dihydroindole, 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester according to example 5, steps A] to C]. The hydrochloride salt of the title compound was obtained according to example 2. MS (ISP): 399.3 (MNa+), 377.3 (MH+). 1H-NMR (DMSO-d6): 2.05 (m, 2H), 2.17 (m, 2H); 2.94 (t, 2H), 3.16(m, 2H), 3.38 (m, 5H), 3.60 (m, 1H), 4.00-4.30 (m, 5H), 4.85 (t, 1H), 6.55 (d, 1H), 7.20 (d, 2H), 7.21 (s, 1H), 9.10 (broad s, 2H). (+Rotamer).

According to the analysis of related databases, 459817-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (60%, 120mg, 3.0mmol) was added to a solution of 2-tert-butoxycarbonylamino-3-fluorobenzoic acid methyl ester from Example 20A (750mg, 2.8mmol) in DMF (8.0ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 30min. (2-bromoethyl)carbamic acid benzyl ester (360mg, 2.8mmol) and sodium iodide (420mg, 2.8mmol) were added and the mixture was heated at 65C for 18h. The mixture was cooled and evaporated in vacuo. The residue was partitioned between EtOAc and brine and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (EtOAc:pet. ether 30:70) to give a colourless gum; yield 340mg, 27%.

The chemical industry reduces the impact on the environment during synthesis Benzyl (2-bromoethyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FERRING B.V.; WO2006/18443; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, 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. Formula: C9H10BrNO

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 × 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

The synthetic route of 54616-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 672-58-2,Some common heterocyclic compound, 672-58-2, name is 3-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

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

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
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 749927-69-3 as follows. COA of Formula: C8H7BrFNO

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (900 mg, 3.9 mmol), 5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (710 mg, 3.2 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) and potassium carbonate (1.3 g, 9.7 mmol) in toluene (6.0 mL) and ethanol (3.0 mL) and water (3.0 mL) was heated at 110 0C for 2 hours. After cooling to RT, the reaction mixture was quenched with water and extracted with diethyl ether. The solid was filtered and washed with water and diethyl ether to afford the desired product (720 mg).

According to the analysis of related databases, 749927-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics