Category: amides-buliding-blocks

3144-09-0, 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. 3144-09-0, name is Methylsulfonamide, A new synthetic method of this compound is introduced below.

A solution of Boc20 (41.2 g, 189.2 mmol) in DCM (200 mL) was added dropwise to a stirred suspension of methane sulfonamide (15.0 g, 157.7 mmol), Et3N (23.6 mL, 173.5 mmol) and DMAP (1.9 g, 15.8 mmol) in DCM (200 mL). The resulting suspension was stirred for 3 h at room temperature and concentrated under vacuum. The resulting residue was diluted with EtOAc (300 mL) and acidified with 1 N HCI (200 mL). The organic layer was washed with water followed by brine, dried over Na2S04 and concentrated under reduced pressure to obtain a crude mixture, which was triturated with 10% EtOAc in petroleum ether to obtain B1 as a white solid (25.0 g, 81 %). Rf: 0.6 (50% EtOAc in petroleum ether). LCMS m/z = 194.3 (M – H). 1H NMR (400 MHz, CDCI3): delta 1.44 (s, 9H), 3.19 (s, 3H), 7.19 (s, 1 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; PFIZER INC.; CHEKLER, Eugene Lvovich Piatnitski; GILBERT, Adam Matthew; UNWALLA, Rayomand Jal; VERHOEST, Patrick Robert; ANDERSON, James Thomas; WO2015/181676; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, 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 3984-14-3. 3984-14-3

EXAMPLE 10 8-cyclohexyl-N-[(dimethylamino)sulfonyl]-1,1a,2,12b-tetrahydro-1a-[[(cis)-2,6-dimethyl-4-morpholinyl]carbonyl]-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxamide. A 2M solution of oxalyl chloride (0.1 mL, 0.2 mmol) in CH2Cl2 was added dropwise to a solution of rel-8-cyclohexyl-1a-[[(cis)-2,6-dimethyl-4-morpholinyl]carbonyl]-1,1a,2,12b-tetrahydro-11-methoxy-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (54 mg, 0.1 mmol) in CH2Cl2 (10 mL) containing one drop of DMF. The reaction mixture was stirred at rt. for 2 h, afterwhich it was concentrated and dried under high vacuum. The resultant residue was dissolved in THF (10 mL) and a solution of N,N-dimethylsulfonamide (24.8 mg, 0.2 mmol) and DIPEA (0.052 mL, 0.3 mmol)) in THF (2 mL) was added. This was followed by the addition of DMAP (10 mg), after which the reaction mixture was stirred at rt. for 10 min, and then at 50 C. overnight. It was then concentrated and the residue purified by preparative reverse phase HPLC to afford the title compound as a white solid, (19.0 mg, 31% yield). MS m/z 649 (MH+), Retention time: 3.685 min; 1H NMR (500 MHz, CD3OD) delta ppm. Compound was observed to exist as inter-converting rotamers, as evidenced from the compound’s NMR spectrum.

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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/60565; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

14433-76-2, 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 14433-76-2 as follows.

(0084) The hydrogenolysis of N,N-dimethyldecylamine works best with a 1:2 molar ratio of [Ru(triphos-(OMe)2)TMM] and B(C6F5)3. Thus, when N,N-dimethyldecylamine (1.0 mmol) was reacted at 160 C. under an atmosphere of H2 (100 bar) with [Ru(triphos-(OMe)2)TMM] (10 mumol) and 2 mol % B(C6F5)3, a conversion of 99% of the amide was observed. The reaction produced 3% decanol and 97% dimethyldecylamine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 14433-76-2, and friends who are interested can also refer to it.

Reference:
Patent; Eastman Chemical Company; KLANKERMAYER, Juergen; WESTHUES, Stefan; LEITNER, Walter; HEMBRE, Robert Thomas; (11 pag.)US2019/345178; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

782-45-6, These common heterocyclic compound, 782-45-6, name is 4-Amino-N-phenylbenzamide, 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.

The pale yellow solid was dissolved in 20 ml of dry methylene chloride solution, c was added, a solution of triethylamine (0.07 ml) in dry dichloromethane was added dropwise and the mixture was stirred overnight at room temperature. TLC, filtration and drying were followed by treatment with 10 ml of acetic acid Ethyl acetate was heated to reflux, filtered and dried to give 0.030 g of a yellow solid with a yield of 12.5%.

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 782-45-6.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ye Fei; Tang Yanbo; Tian Jinying; Guo Zongru; Chen Zheng; Zhang Xiaolin; He Yibo; Ma Yiming; Chen Ling; Han Jing; (27 pag.)CN102382076; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

53297-70-4, 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. 53297-70-4, name is 4-Amino-3-methylbenzenesulfonamide, A new synthetic method of this compound is introduced below.

The compounds in Table 2 below were prepared in accordance with the procedures set forth in Example 1, Step 3 using either [(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (prepared as described in Example 1, Steps 2 and 3) or the appropriate counterpart and the appropriate amine in place of 2-chloro-3-aminopyridine.

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; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2005/115147; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

42137-88-2, 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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

B. Dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine. 57 g (0.2618 mole) of dextrorotatory (+)-(4-chlorophenyl)phenylmethylamine (prepared in Example 1.2) and 86.4 g (0.2917 mole) of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (prepared in Example 2.3) are added to 200 ml (1.15 mole) of ethyldiisopropylamine in a 500 ml three-necked round-bottomed flask. The mixture is heated under reflux for 3 hours, then poured in 400 ml of methanol and the mixture is cooled, in an ice bath, and stirred for 1 hour. The precipitate which forms is filtered off, washed with methanol and dried under vacuum at 50 C. 88.6 g of dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine are obtained. M.P. 173.3 C. Yield: 76.7%. [alpha]D25: +43.2 (c=0.5, toluene). Optical purity: 98.35%. Analysis for C24 H25 ClN2 O2 S in %: Calc.: C 65.38 H 5.71 N 6.35 C 8.04 S 7.27 Found: 64.98 5.70 6.40 7.96 7.35

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; U C B, S.A.; US5478941; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, 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 354-38-1 as follows.

2-Methyl-2-(methylsulfinyl)propanenitrile (Int-3, 9.8 g, 74.7 mmol) was dissolved in dichloromethane (390 mL) at 0-5C (ice bath) and 2,2,2-trifluoroacetamide (17.0 g, 151 mmol), magnesium oxide (12.7 g, 307 mmol) and rhodium(II) acetate dimer (850 mg, 1.92 mmol) were added subsequently. Finally, a solution of iodobenzene diacetate (36.3 g, 113 mmol) in dichloromethane (98.0 mL) was added and the mixture was stirred for 1 h at 0-5C, followed by 6 h at room temperature. Then, a second portion of rhodium(II) acetate dimer (850 mg, 1.92 mmol) was added and the suspension stirred for additional 95 h at room temperature. The reaction mixture was filtered, the residue was washed with dichloromethane (100 mL) and the combined filtrate was concentrated in vacuo to afford a dark oil as crude product. After column chromatography (silica gel, 100 g, eluting with ethyl acetate / n-heptane, gradient 10:90 to 50:50) and drying in vacuo (50C, 5 mbar) the title compound was isolated as a light yellow oil, that solidified upon standing (13.74 g, 76%). HPLC (method LCMS_fglm) tR = 0.97 min. 1H NMR (CDC13, 400 MHz): delta 1.91 (s, 3 H), 1.91 (s, 3 H), 3.65 (s, 3 H). MS (ES-) m/z 241.1 [M-H] ,

According to the analysis of related databases, 2,2,2-Trifluoroacetamide, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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 6292-59-7.

General procedure: Sulfonamide 10a (2.0 g, 6.2 mmol, 1.1 eq) was solvedin dry THF (8 ml) and cooled to 78 ¡ãC under a nitrogen atmosphere.n-BuLi (1.62 N solution in hexane, 7.70 ml, 2.2 eq) wasadded drop-wise. After the addition was completed, the solutionwas stirred for 15 min, then the temperaturewas allowed to raise at60 ¡ãC and the THF was evaporated under very high vacuum. DMFwas added (10 ml), followed by dichloropyrimidine intermediate 9(2.0 g, 5.7 mmol, 1.0 eq) and the mixture was stirred overnight at50 ¡ãC. The reaction mixture was poured onto a 1:1 mixture ofwater-ice and the aqueous phase was washed with DEE, thenacidified with HCl and the resulting precipitate was filtrated off,washed with water and dried at 110 ¡ãC to afford a bright yellowsolid (2.22 g, yield 61.2percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lepri, Susan; Goracci, Laura; Valeri, Aurora; Cruciani, Gabriele; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 658 – 670;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, 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 177906-48-8 as follows.

Example 40 {4-[3-(6-Bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester A mixture of 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine (from Example 38 supra) (1.94 g, 6.27 mmol), trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.61 g, 7.52 mmol), K2CO3 (1.04 g, 7.52 mmol) in DMF (20 mL) was stirred at 140 C. for 15 hours. The solution was then cooled to room temperature and poured into water. The resulted solid was filtered and washed with water. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give {4-[3-(6-bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 0.512 g, 17%). LC-MS: [M+H]+ 487.

According to the analysis of related databases, trans-N-Boc-1,4-cyclohexanediamine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; Soth, Michael; US2012/238564; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 7803-58-9, name is Sulfuric diamide, 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. 7803-58-9

The preparation of sulfamide 16.1 is starting with commercially available, literature or readily available diamine. The treatment of diamine 16.1 with sulfamine a under refluxing pyridine affords sulfamine 16.3, which is followed by alkylation of [A-HALO] alkyl ester to give compound 16.4. Basic hydrolysis (LiOH, [H20/THF/MEOH)] of ester gives acid 16.1 as the intermediateds for example 61.

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 7803-58-9.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2003/106405; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics