Month: January 2021

Electric Literature of 71026-66-9, 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. 71026-66-9 name is tert-Butyl (4-aminophenyl)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.

General procedure: To a solution of 2-chloroethanesulfonyl chloride (1.56 g, 9.57 mmol) in THF (10 mL) was added dropwise N-methylaniline (989 mg, 9.23 mmol) followed by triethylamine (5 mL, 36 mmol) at 0 C. After stirring for 3 h, ethyl acetate was added, and the reaction mixture was washed with 3 M hydrochloric acid then brine, dried over magnesium sulfate, evaporated in vacuo to obtain 1.76 g (97%) of vinylsulfonamide 3a as a pale brown solid. The product was spectroscopically pure, and was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (4-aminophenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Article; Kihara, Nobuhiro; Mitsuhashi, Yuji; Sato, Makoto; Hirose, Shun-Ichi; Goudo, Erika; Uzawa, Yoshinori; Shirai, Natsumi; Hamamoto, Sari; Iwasaki, Ryo; Fujioka, Akane; Tetrahedron Letters; vol. 57; 23; (2016); p. 2563 – 2566;,
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. 36065-27-7, name is N-(1-Phenylethyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 36065-27-7

(2) N-(1-(4-Formylphenyl)ethyl)acetamide To a solution of N-(1-phenylethyl)acetamide (5.0 g) in dichloromethane (100 ml) was added dropwise titanium tetrachloride (16.7 ml) at below 5 C. over 30 min. Thereto was added dropwise a solution of dichloromethyl methyl ether (14.1 ml) in dichloromethane (30 ml) solution at below 5 C. over 30 min. The mixture was stirred at 25 C. for 3 hr, at room temperature for 12 hr, and then at 25 C. for 3 hr, and poured into ice water (800 ml) and extracted with ethyl acetate. The extract was washed successively with a saturated sodium hydrogencarbonate solution (500 ml) and saturated brine (500 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:3) to give the title compound (0.35 g) as a colorless oil. 1H-NMR(CDCl3)delta: 1.48(3H, d, J=7.3 Hz), 2.01(3H, s), 5.17(1H, dt, J=7.1, 7.1 Hz), 6.04(1H, brs), 7.47(2H, d, J=7.9 Hz), 7.84(2H, d, J=8.6 Hz), 9.98(1H, s); MS(EI): 191(M+).

According to the analysis of related databases, 36065-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 255735-88-7, A common heterocyclic compound, 255735-88-7, name is tert-Butyl 2-aminopropylcarbamate, molecular formula is C8H18N2O2, 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.

Ethyl 4-chloro-1-methyl-6-nitro-2-oxo-1 ,2-dihydroquinoline-3-carboxylate (Intermediate F2; 325 mg, 1.05 mmol), tert- butyl (2-aminopropyl)carbamate (200 mg, 1.15 mmol) and DIPEA (0.2 ml_, 1.15 mmol) were combined in a microwave vial and dissolved in THF (5.2 ml_). The reaction mixture was then heated to 100 C for 16 h. Excess amine was added in 1 ml_ of THF followed by DIPEA (50 uL) and heating was continued for 2 h. The reaction mixture was cooled to rt, partitioned between EtOAC (25 ml_) and water (25 ml_). The aqueous layer was further extracted with EtOAc (25 ml_) and the organic extracts were combined, washed with brine (50 ml_), dried (MgSCU) and concentrated in vacuo affording ethyl 4-((1-((te/f-butoxycarbonyl)amino)propan-2-yl)amino)-1-methyl-6-nitro-2-oxo- 1.2-dihydroquinoline-3-carboxylate (606 mg, 129%) as a yellow solid that was used without further purification. LCMS (Method T4); RT 2.87 min; m/z 449.2078 [M+H]+. Note: The LCMS showed a mixture of the desired product and amine starting material. This mixture was carried forward assuming 100% conversion.

The synthetic route of 255735-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (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. 23363-88-4, name is N-(4-Hydroxycyclohexyl)acetamide(cis- and trans- mixture), This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H15NO2

To a suspension of 4-ACETAMIDO-CYCLOHEXANOL (100 g) in water (300 ml) was added a solution of 10% sodium hypochlorite (500ml) and the contents stirred at room temperature for 12 hours. To this was added liquid bromine (112 g) and further reactions carried out as described in Example 1.

According to the analysis of related databases, 23363-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cipla Ltd; Wain, Christopher, Paul; WO2004/41797; (2004); A1;,
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 24243-71-8 as follows. Computed Properties of C3H9NO2S

EXAMPLE 14 (+-)-trans-N-(6-Butoxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-ethyl-methanesulfonamide STR29 The compound was obtained from 6-butoxy-2,2-dimethyl-3,4-epoxychroman (Example 5d) and ethyl-methanesulfonamide similarly to Example 5e. After silica gel chromatography using methylene chloride/methanol 97:3, the title compound of a melting point of 139-140 C. was isolated.

According to the analysis of related databases, 24243-71-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Marion Roussel Deutschland GmbH; US6008245; (1999); A;,
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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H6F3NO2S

Dissolve 2,6-dimethoxynaphthalene 37.6 g (0.20 mol) and 4-(2-(piperidin-1- yl) ethoxy) benzoyl chloride 64.0 g (0.21 mol) in 800 mL of dichloromethane. Add aluminum chloride 133 g (1.00 mol) portionwise and slowly (the first 30 to 50 g must be added slowly to keep the acylation reaction under control so the solvent does not boil off). After all the aluminum chloride has been added, stir the reaction until no more undemethylated compound can be detected either by TLC or HPLC (about 5 hours). Slowly pour the reaction mixture into 1 L of ice/water with vigorous stirring. Decant the top layer water into a separation funnel. Wash the dichloromethane solution and the precipitate with 2N HCl and decant the aqueous layer again into the separation funnel. Extract the aqueous layer with dichloromethane. Adjust the combined dichloromethane solution and the precipitate pH to 8 first with IN NaOH then with saturated NaHCO3. Filter the mixture. Slurry the solid repeatedly with dichloromethane. Separate the layers of the filtrate and extract the aqueous phase with dichloromethane. Wash the combined organic with brine and dry over MgS04. Treat the dichloromethane solution with charcoal and filter through a prepackaged”suppelco”silica gel funnel. Evaporate the solvent to give 61.2 g (75.5%) of 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-benzoyl]- naphthalen-2-ol. Couple 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol and 2,4-dibenzyloxyphenyl boronic acid to provide 2- (2, 4-dibenzyloxyphenyl)-6-methoxy-l- [4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalene by the procedure analogous to that described above in the procedure for 5- {6-benzyloxy-1- [4- (2-piperidin-1-yl-ethoxy)- phenoxy]-naphthalen-2-yl}-2-methyl-isoindole-1, 3-dione. Dissolve 10.5 g (20.0 mmol) 2- (2, 4-dibenzyloxyphenyl)-6-methoxy-l- [4- (2- piperidin-1-yl-ethoxy)-benzoyl]-naphthalene in 150 mL of THF. Add LAH 1.5 g (37.0 mmol) portionwise with vigorous stirring at 0 C. After the addition, allow the reaction to warm up to room temperature and then stir for 3 hours. Cool the reaction in an ice bath and slowly quench with saturated Na2SO4. Filter off the solid A1203 and wash the filter cake with THF (2x50mL). Combine the filtrates, concentrate and purify the residue by flash chromatography on silica gel using CH2Cl2 : MeOH (9: 1) as eluent to afford 2- methoxy-5- {hydroxy- [4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2, 4- benzyloxyphenyl)-naphthalene. Heat 2-methoxy-5- {hydroxy- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6- (2, 4- benzyloxyphenyl) -naphthalene to 60C in THF containg 10% (by weight) of Pd/C (30%) catalyst, overnight under 50 psi of hydrogen atmosphere to afford 2-methoxy-5- {hydroxy- [4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2-hydroxy-4-benzyloxyphenyl)- naphthalene. Treat the THF solution of 2-methoxy-5- {hydroxy- [4- (2-piperidin-1-yl- ethoxy)-phenyl]-methyl}-6- (2-hydroxy-4-benzyloxyphenyl)-naphthalene with 10% (by mol) of concentrated HCl to give I-12- [4- (8-benzyloxy-2-methoxy-5H-6-oxa-chrysen-5- yl)-phenoxy]-ethyl}-piperidine. Dissolve 1- {2- [4- (8-benzyloxy-2-methoxy-5H-6-oxa-chrysen-5-yl)-phenoxy]- ethyl}-piperidine (680 mg) in a mixture of 250 ml ethanol and 150 ml THF with warming. Add a slurry of 300 mf 10 % Pd/C in ethanol and react under 1 atmosphere of hydrogen for 18 hours. Filter the catalyst and evaporate the solvent to yield 465 mg of 2- methoxy-5- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-8-ol. Dissolve 2-methoxy-5- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-8- ol (118 mg. , 0.245 mmoles) in 20 ml methylene chloride and add N- phenyltrifluoromethanesulfonimide (400 mg, . 1.12 mmoles) followed by 1.0 ml of diisopropylethyl amine and stir for 72 hours. Evaporate the solution to a paste and purify by running through an SCX column in methanol (elute with 2N ammonia/methanol) to give 125 mg of the title compound: 125 mg (83%).

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; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 3984-14-3, The chemical industry reduces the impact on the environment during synthesis 3984-14-3, name is N,N-Dimethylsulfamide, I believe this compound will play a more active role in future production and life.

(+/-)-13-Cyclohexyl-N-[(dimethylamino)sulfonyl]- 6, 7-dihydro-6-hydroxy -5H- indolo[2, 1-a] [2]benzazepne-l 0-carboxamide.l-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (11.5mg, 0.06 mmol) was added to a solution of (+/-)13-cyclohexyl-6,7-dihydro-6-hydroxy – 5H-indolo[25l-a][2]benzazepine-10-carboxylic acid (7.5 mg, 0.02 mmol) and DMAP(7.4 mg, 0.06 mmol) in DMF (0.5 mL) and CH2Cl2 (0.5 mL) at 22 C. The vial was shaken for a minute at 22 0C. N5N-Dimethylsulfamide (4.9 mg, 0.04 mmol) was then added. Stirring was continued for 18 hr. The solution was filtered and purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac to leave the titled compound as a white film (3.0 mg, 30 %). ESI-MS m/z 482 (MH+); IH NMR (500 MHz, MeOD) delta 1.26- 1.34 (m, 1 H) 1.40-1.55 (m, 2 H) 1.63 (m, 1 H) 1.82 (m, 2 H) 1.96 (m, 1 H) 2.01-2.19 (m, 3 H) 2.36 (m, 1 H) 2.95-3.08 (m, 2 H) 3.03 (s, 6 H) 3.76 (dd, J=15.26, 3.36 Hz, 1 H) 4.41-4.69 (m, 2 H) 7.40-7.50 (m, 4 H) 7.60 (m, 1 H) 7.93 (m, 1 H) 8.11 (m, 1 H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/92000; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 713-41-7, 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. 713-41-7, name is 2-Amino-4-(trifluoromethyl)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

-(4-Chlorophenyl)-7-trifluoromethyl-3H-quinazolin To a stirred suspension of 2-amino-4-(trifluoromethyl)benzamide (33.6 g, 0.16 mol) in water (750 mL) was added dropwise 4-chlorobenzaldehyde. Iron trichloride hexahydrate (133 g) was then added in portions. The reaction mixture was then heated at reflux for 24 h. After allowing the suspension to cool to room tempera- ture, the precipitate was isolated by vacuum filtration washing with water (3 x 500 mL) and dried under vacuum (10 mbar, 50C). Yield = 50 g, 94%; HPLC-mass spectrometry (LC-MS): 3.7 min, 325 (M+).

The synthetic route of 2-Amino-4-(trifluoromethyl)benzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; GROss, Steffen; POHLMAN, Matthias; NARINE, Arun; ROSENBAUM, Claudia; DESHMUKH, Prashant; DICKHAUT, Joachim; BANDUR, Nina Gertrud; KOeRBER, Karsten; KAISER, Florian; VON DEYN, Wolfgang; LANGEWALD, Juergen; CULBERTSON, Deborah L.; EBUENGA, Cecille; WO2011/36074; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 24310-36-9, 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 24310-36-9 as follows.

Step 5. Preparation of 1, 2,3, 4-Tetrahydro-benzo [b] azepin-5-one. To preheated polyphosphoric acid (PPA, 220 g) at 70-80 C was added 1- (Toluene-4-sulfonyl)-1, 2,3, 4-tetrahydro-benzo [b] azepin-5-one (50.0 g, 0.16 mol). The mixture was stirred for 3.0 h at the same temperature and then poured into ice water. After the pH was adjusted to about 8-9 by adding aq NaOH, the mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgS04, and concentrated. The residue was purified by silica gel column chromatography (eluent, 3: 1 n-hexanes: ethyl acetate) to give 1, 2,3, 4-Tetrahydro-benzo [b] azepin-5-one (22g).

According to the analysis of related databases, 24310-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 683-57-8, 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. 683-57-8, name is 2-Bromoacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-chiorophenol (2.57 g, 20.0 mmol), 2-bromoacetamide (2.76 g, 20.0 mmol) and K2C03 (5.53 g, 40.0 mmol) in acetone (40 mL) was stirred at 70 C overnight. The mixture was then cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE / EtOAc (V / V) = 1: 1) to give the title compound as a white solid (3.22 g, 87%).

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-Bromoacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics