Author: Jessica.F

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. 96-72-0, name is 2-Chloro-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H5ClN2O4S

The compound 4 (14.15 g, 59.8 mmol) and 300 mL of methanol were placed into a flask and stirred at 50 C until dissolved completely and then 10% Pd/C (1.4 g) was added. The mixture was intensively stirred under H2 at 50 C and monitored with TLC. After 4 h, the reaction was complete, and the suspension was filtered. The resulting solution was evaporated to give the crude product. It was dissolved in 30 mL of 9 mol/L hydrochloric acid solution and filtered. The filtrate was alkalified with 10 mol/L sodium hydroxide solution to pH 7. The suspension was filtered to afford the compound 5 (10.27 g, 83% yield, m.p. 166-167 C). 1H NMR (400 MHz, DMSO-d6) delta (ppm): 7.969 (d, 1H, JH = 8.8 Hz, Ar-H), 8.017 (s, 2H, SO2NH2), 8.414-8.442 (m, 1H, Ar-H), 8.671-8.677 (m, 1H, Ar-H).

According to the analysis of related databases, 96-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pan, Li; Jiang, Ying; Liu, Zhen; Liu, Xing-Hai; Liu, Zhuo; Wang, Gang; Li, Zheng-Ming; Wang, Di; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 18 – 26;,
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Reference of 5349-24-6, 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. 5349-24-6 name is N-Butyl-2-chloroacetamide, 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.

General procedure: Triethylamine (0.3643 g, 3.6 mmol) was added to a solution of the appropriate alkylamine or substituted benzylamine 5a-l (3 mmol) in dichloromethane (7.5 mL), and the reaction mixture was stirred for 5 min at room temperature, then 2-chloroacetyl chloride (0.3857 g, 3.6 mmol) was added dropwise to this reaction mixture at 0 C and stirred for 15 min at room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure to afford 6a-l. KI (0.5976 g, 3.6 mmol) and CTAB (98.40 mg, 7.5% mmol) were added to a solution of the crude product 6a-l in acetone (30 mL) and maintained stirring at reflux for 2 h to afford 7al. K2CO3 (0.2073 g, 3 mmol) was added to a solution of scopoletin (0.3843 g, 2 mmol) in acetone (30 mL), and the reaction mixture was stirred at refluxed for 30 min. Then crude intermediates 7a-l were added into the mixture and maintained reflux for 8-12 h (the reaction progress was monitored by TLC with UV detection). After cooling the reaction and filtration, the solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, washed with saturation sodium bicarbonate, and saturation salt solution successively, dried over anhydrous sodium sulfate, evaporated under reduced pressure to give the target crude products. The crude products were purified by column chromatography using petroleum ether/ethyl acetate from 6:1 to 2:1 as the gradient eluent system to yield the products 26-37.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Butyl-2-chloroacetamide, and friends who are interested can also refer to it.

Reference:
Article; Luo, Jinxiang; Lai, Ting; Guo, Tao; Chen, Fei; Zhang, Linli; Ding, Wei; Zhang, Yongqiang; Molecules; vol. 23; 5; (2018);,
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Application of 4815-28-5,Some common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, molecular formula is C9H12N2OS, 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: A solution of 2-aminothiophene derivatives 1a-c (0.01 mol) in 7.2 mL conc. HCl and 4 mL H2O was stirred and cooled in ice bath. Then, a solution of NaNO2 (0.690 g,0.01 mol) in 8 mL H2O was added dropwise for 10 min. The cold diazonium solution was added slowly to awell-stirred solution of 3-iminobutanenitrile (0.82 g, 0.01mol) or 1-phenyl-2-thiocyanatoethanone (1.78 g, 0.01mol), in ethanol (60 mL) containing sodium acetate (4 g, 0.05 mol). The reaction mixture was stirred for another3 h. The formed precipitate was filtered off, dried well, and recrystallized from ethanol/benzene to give 3a-c and 7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, its application will become more common.

Reference:
Article; Gouda, Moustafa A.; Eldien, Hadeer Fakhr; Girges, Margret M.; Berghot, Moged A.; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 401 – 405;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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.

A mixture of 29 (0.123 g; 0.27 mmol), 139 (0.063 g, 0.30 mmol), NaI (0.040g ; 0.27 mmol) and K2CO3 (0.045 g; 0.32 mmol) in dimethylacetamide (3 ml) was heated at [85C] under argon atmosphere for 3 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient [1-3%] of 3.5 N [NH3 IN MEOH/METHYLENE] chloride to give after trituration in ether/pentane Example 51 as a white solid. Yield: [78%] MS-ESI: 631 [[M+H] +] [1H NMR (CDC13)] : 1.31 (m, 6H); 1.45 (s, 9H); 1.50-1. 75 (m, 4H); 1.62 (s, 6H); 2.35 (s, 6H); 2.72 (m, 2H); 2.80 (m, 4H); 2.94 (m, 2H); 3.25 (br m, 2H); 3.55 (br m, 2H); 4.10-4. 20 (br m, 1H); 4.70-4. 80 (br m, 1H); 6.74 (s, 1H) ; 6.95 (s, 1H); 7.07 (s, 2H); 8.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1746-77-6, 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. 1746-77-6, name is Isopropyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 1-4 (120 mg, 294 imol, 1 eq), isopropyl carbamate (45.5 mg, 441 imol, 1.5eq) and Cs2CO3 (287.3 mg, 881 .9 imol, 3 eq) in dioxane (3 mL) was added XantPhos (34.0 mg,58.8 imol, 0.20 eq) and Pd2(dba)3 (26.9 mg, 29.4 imol, 0.10 eq) under an Argon atmosphere. The mixture was heated to 90C and stirred for 4 hours. The mixture was quenched by addition of 1 M HOAc and purified by prep-HPLC (column: Boston pH-lex 150*25 bum; mobile phase: [water(0.225%FormicAcid)-acetonitrile]; B%: 33%-63%,10 mm followedby further purification on column: Phenomenex Gemini C18 250*50mm*10 um; mobile phase:[water (0.05% ammonia hydroxide v/v)-acetonitrile]; B%: 28%-58%,12 mm). Compound 168was obtained as a yellow solid. 1H NMR (400 MHz, Methanol-d4), O ppm, 8.64 (br d, J = 2.26Hz, 1 H), 8.61 (br d, J = 2.64 Hz, 1 H), 8.44 (br s, 1 H), 8.10 (dd, J = 6.71, 2.70 Hz, 1 H), 7.60 -7.67 (m, 1 H), 7.33 (dd, J = 10.92, 9.16 Hz, 1 H), 5.25-5.47 (m, 1 H), 5.01 (dt, J = 12.52, 6.23Hz, 1 H), 4.32-4.43 (m, 2 H), 4.07-4.19 (m, 2 H), 1.33 (d, J = 6.27 Hz, 6 H). Method 1: RT =2.88 mm.; M+H = 431.1.

The synthetic route of Isopropyl carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; LERARIO, Isabelle K.; LIANG, Fang; LIU, Xiaodong; MOLTENI, Valentina; NAGLE, Advait Suresh; NG, Shuyi Pearly; RATNIKOV, Maxim; SMITH, Jeffrey M.; XIE, Yongping; (167 pag.)WO2018/220531; (2018); A1;,
Amide – Wikipedia,
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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. 103500-22-7, name is Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H15NO3

Dissolve the previous product 1-4 (838.5mg, 4mmol) in 50ml of tetrahydrofuran,Cbz-1-aminocyclopropanemethanol (885 mg, 4 mmol) was added, triphenylphosphine (1.31 g, 5.0 mmol) was added, and diethyl azodicarboxylate (DEAD) (970.7 mg, 5.0 mmol) was added,The reaction was stirred at room temperature overnight, filtered, the filtrate was extracted with ethyl acetate, washed with water, and purified by column chromatography to obtain 500 mg of white solid product (1-6), MS: 413, yield: 30.3%.

According to the analysis of related databases, 103500-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Li Haibo; Lv Haibin; Li Xinghai; Chen Yuanwei; (14 pag.)CN110551065; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 127828-22-2, These common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)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.

General procedure: (S)-4-(4-chlorophenyl)-6-(2-methoxy-2-oxoethyl)-3 ,9-dimethyl-6H-thieno [3,2- fj [1 ,2,4jtriazolo[4,3-aj [1 ,4jdiazepine-2-carboxylic acid (CAS 916493-82-8) (44 mg, 0.1 mmol), mono-Boc-amino-PEG-amine (1.5 eq), HATU (1.5 eq), and N,Ndiisopropylethylamine (1.5 eq) were added to DMF (0.1 M). The mixture was stirred for 4 hours at room temperature. The mixture was diluted with ethyl acetate, washed with iN NaOH and brine, dried over Na2504, filtrated and concentrated under reduced pressure. The residue was purified by flash chromatography to give mono-amides (93%). The mono-amide was dissolved into dichloromethane (0.5 M). Trifluoroacetic acid (0.5 M) was added to the solution. The mixture was stirred for 1 hour at room temperature. The mixture was diluted with dichloromethane, washed with iN NaOH, dried over Na2504, filtrated and concentrated under reduced pressure. The free amine was used for the next step without purification. The free amine, (S)-4-(4-chlorophenyl)-6-(2-methoxy-2-oxoethyl)-3 ,9-dimethyl-6H-thieno [3,2- fj [1 ,2,4jtriazolo[4,3-aj [1 ,4jdiazepine-2-carboxylic acid (CAS 916493-82-8) (1.1 eq), HATU (1.5 eq), and N,N-diisopropylethylamine (1.5 eq) were added to DMF (0.1 M). The mixture was stirred for 4 hours at room temperature. The mixture was diluted with ethyl acetate, washed with iN NaOH and brine, dried over Na2504, filtrated and concentrated under reduced pressure. The residue was purified by flash chromatography to give the titled compounds (55%, for 2 steps).

The synthetic route of 127828-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; QI, Jun; TANAKA, Minoru; ROBERTS, Justin, M.; (314 pag.)WO2017/91673; (2017); A2;,
Amide – Wikipedia,
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194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, 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. Recommanded Product: tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate

General procedure: Oxime 1 (20 mg, 51.5 mumol) and HOBt.H2O (7.9 mg, 51.5 mumol)were dissolved in 1.5mL of DMF and DIC (8 muL, 51.5 mmol) wasadded. It was stirred for 5 min, then tert-butyl 2-aminoethylcarbamate hydrochloride (20 mg, 102 mumol) and DIEA(18 muL, 102 mumol) were added to the solution. The mixture wasstirred at 50 C for 16 h then it was evaporated in vacuo. The crudeproduct was purified by column chromatography on silica gel 60with CHCl3-MeOH (8:2) to give 22.2 mg (81%) of 2 as yellowish oil.

The synthetic route of 194920-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dvoracsko, Szabolcs; Keresztes, Attila; Mollica, Adriano; Stefanucci, Azzurra; Macedonio, Giorgia; Pieretti, Stefano; Zador, Ferenc; Walter, Fruzsina R.; Deli, Maria A.; Kekesi, Gabriella; Banki, Laszlo; Tuboly, Gabor; Horvath, Gyoengyi; Toemboely, Csaba; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 571 – 588;,
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. 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 77925-80-5

[0232] A solution of 2-nitrobenzene-1-sulfonyl chloride (500 g, 2.26 mol) in pyridine (1500 mL) was added dropwise to a solution of O-benzylhydroxylamine hydrochloride (400 g, 2.51 mol) in pyridine (1500 mL) at 0 C. The reaction mixture was then stirred at 20 C. overnight. The mixture was concentrated in vacuum, diluted with DCM and washed with HCl (10%) three times. The combined organic layer was concentrated in vacuum and re-crystallized with DCM to afford N-(benzyloxy)-2-nitrobenzenesulfonamide (485 g, 62.6%) as a yellow solid. [0233] To a solution of N-(benzyloxy)-2-nitrobenzenesulfonamide (212 g, 0.69 mol) in THF (1000 mL) was added (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (171 g, 0.63 mol) and PPh3 (275 g, 1.05 mol), followed by dropwise addition of a solution of DEAD (195 g, 1.12 mol) in THF (500 mL). The mixture was then stirred at 20 C. overnight. The reaction mixture was then concentrated in vacuum and purified by silica gel column chromatography (3:1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (283.8 g, 80%) as a yellow oil.

According to the analysis of related databases, 77925-80-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gu, Yu Gui; He, Yong; Yin, Ning; Alexander, Dylan C.; Cross, Jason B.; Busch, Robert; Dolle, Roland E.; Metcalf, III, Chester A.; US2013/296555; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 40545-33-3, These common heterocyclic compound, 40545-33-3, name is 2-Amino-5-methylbenzamide, 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 cold (0-5 C) stirred suspension of aminobenzamides 10a-c (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate 3-phenylacryloyl chloride 11c-k was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from ethanol.

Statistics shows that 2-Amino-5-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 40545-33-3.

Reference:
Article; Raffa, Demetrio; Maggio, Benedetta; Plescia, Fabiana; Cascioferro, Stella; Plescia, Salvatore; Raimondi, Maria Valeria; Daidone, Giuseppe; Tolomeo, Manlio; Grimaudo, Stefania; Di Cristina, Antonietta; Pipitone, Rosaria Maria; Bai, Ruoli; Hamel, Ernest; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2786 – 2796;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics