Tag: M.W=200-300

Electric Literature of 111300-06-2, 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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of lithium aluminium hydride (9 g, 0.23 mol) in tetrahydrofuran (425 mL) was added slowly tert-butyl (trans-4-hydroxycyclohexyl)carbamate (intermediate 1, 10 g, 0.046 mol). The mixture was refluxed overnight. Once the mixture was cooled to room temperature, 9 ml of water, 9 ml of 4N NaOH solution and 18 ml of water were carefully and successively dropped. The organic solvent was removed under reduced pressure and the crude obtained was dissolved with chloroform and dried over magnesium sulphate. The filtrate was evaporated to dryness and co evaporated with hexane to give the title compound as a white solid (89%). This intermediate is also described in . 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.04 – 1.20 (m, 2 H) 1.25 – 1.40 (m, 2 H) 1.97 (br. s., 4 H) 2.27 – 2.40 (m, 1 H) 3.57 – 3.70 (m, 1 H)

The synthetic route of tert-Butyl (trans-4-hydroxycyclohexyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; Aiguade Bosch, Jose; Gual Roig, Silvia; Prat Quinones, Maria; Puig Duran, Carlos; EP2592077; (2013); A1;,
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Reference of 75178-90-4,Some common heterocyclic compound, 75178-90-4, name is tert-Butyl (5-hydroxypentyl)carbamate, molecular formula is C10H21NO3, 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 stirred mixture of tert-butyl 5-hydroxypentylcarbamate (2)(9.8 g, 48.2 mmol) and triethyl amine (13.44 mL, 96.0 mmol) in DCM (85 mL) at-10 oC was added methanesulfonyl chloride (4.5 mL, 57.9 mmol) in adropwise fashion and the resulting solution was stirred at the same temperaturefor 3h. The reaction was quenched with the addition of water (5 mL). Theorganic phase was washed with water, brine, dried over MgSO4,filtered and evaporated under reduced pressure to afford the title compound asyellow oil (13.16g, 97%). The product was directly taken to next step withoutany further purification. 1H NMR(CDCl3) d 4.22 (t, 2H, J = 6.42 Hz), 3.09 (m, 2H), 1.82 (m, 4H), 1.56-1.40(m, 11H). 13C NMR (75 MHz, CDCl3) d 155.8, 79.3, 70.0,41.8, 37.9, 29.8, 28.3, 22.5. IR: 2981, 1707, 1516, 1354, 1171 cm-1. MS m/z (ESI) 304.26 (M +Na+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (5-hydroxypentyl)carbamate, its application will become more common.

Reference:
Article; Maharvi, Ghulam M.; Bharucha, Adil E.; Fauq, Abdul H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 9; (2013); p. 2808 – 2811;,
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Application of 117009-97-9,Some common heterocyclic compound, 117009-97-9, name is Benzyl 1,4-diazepane-1-carboxylate, molecular formula is C13H18N2O2, 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.

Compound BB-18-3 (1.8g crude) was dissolved in dilute hydrochloric acid (6M, 40mL) was stirred until uniform, slowly under nitrogenwas added dropwise sodium nitrite solution (2N, 17mL), then stirred at room temperature for 1 hour, 50mL of water was added, extracted with ethyl acetate(60mL ¡Á 3).The combined organic phases with saturated brine (20 mL), dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give the titlecompound BB-18-4 (2g crude) was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzyl 1,4-diazepane-1-carboxylate, its application will become more common.

Reference:
Patent; Changzhou Yin Sheng Pharmaceutical Co., Ltd.; Sichuan University; Zhang, Yang; Fu, Zhifei; Li, Jian; Chen, Shuhui; Wei, Yuquan; Tao, Xin; (65 pag.)CN105732602; (2016); A;,
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Some common heterocyclic compound, 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H22N2O2, 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. Formula: C12H22N2O2

step 2-A mixture of 68b (2 mmol) and 80 (2 mmol) in n-BuOH was heated in a sealed tube at 160 C. for 6 h. When no starting material was detected by TLC, the reaction was cooled to RT and concentrated in vacuo. The crude product 82a was used in the next step without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 207405-68-3, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2008/146595; (2008); A1;,
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Synthetic Route of 177906-48-8, The chemical industry reduces the impact on the environment during synthesis 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, I believe this compound will play a more active role in future production and life.

Method E The reaction mixture of Core C (1.00 eq) and amine n (4.00 eq) in DMSO (8 mL) was stirred at 160 C for 3 h. The reaction mixture was cooled to rt and poured onto ice-H20 (20 mL). The aqueous layer was extracted with EA (50 mL*3). The combined organic layers were washed with brine (50 mL*3), dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography to give A-n. Step 1: Compound 27_2 was made according to the procedure descibed in method E with amine-27 (1.0 eq) and DIEA (10 eq) at 160C for 6 h and it was obtained as a yellow solid after purification by prep HPLC (TFA). Yield: 41.1% NMR (CDCb, 400 MHz) delta 8.18 (d, / = 5.2 Hz, 1H), 7.83 (s, 1H), 6.71 (d, / = 5.6 Hz, 1H), 4.87 (s, 1H), 4.41 (s, 1H), 3.89 – 3.82 (m, 4H), 3.49 (s, 1H), 3.19 (d, / = 6.3 Hz, 2H), 2.19 – 2.05 (m, 4H), 1.46 (s, 9H), 1.35 – 1.29 (m, 7H), 1.26 (m, 2H), 1.23 (m, 2H), 0.50 – 0.46 (m, 2H), 0.26 – 0.24 (m, 2H)

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, trans-N-Boc-1,4-cyclohexanediamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (2017); A1;,
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Related Products of 216961-61-4,Some common heterocyclic compound, 216961-61-4, name is tert-Butyl (10-aminodecyl)carbamate, molecular formula is C15H32N2O2, 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 2. Starting compound III: S-Methyl N-cyano-N-(2-methoxy-5-pyridylisothiourea. Starting compound IV: 10-t-Butoxycarbonylaminodecylamine. Purification: Flash chromatography (Eluent 1% NH3(aq) and 0-6% MeOH in CH2Cl2) and crystallization from ether. 13C NMR (CDCl3) delta: 161.2, 158.6, 155.5, 143.3, 137.0, 127.9, 117.3, 110.3, 77.2, 53.2, 41.3, 29.4, 28.9, 28.8, 28.8, 28.6, 28.6, 28.2, 26.2, 26.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (10-aminodecyl)carbamate, its application will become more common.

Reference:
Patent; Leo Pharmaceutical Products, Ltd. A/S; US6346520; (2002); B1;,
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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 141449-85-6 as follows. category: amides-buliding-blocks

A flask was charged with tert-butyl octahydropyrrolo[3,4-c]pyrrole-2-carboxylate (1.20 g, 5.65 mmol, 1.00 equiv), potassium (bromomethyl)trifluoroboranuide (1.13 g, 5.63 mmol, 1.00 equiv), and THF (15 mL) under nitrogen. The mixture was stirred overnight at 80 C and concentrated under reduced pressure. Potassium carbonate (0.781 g, 5.65 mmol, 1.00 equiv) and acetone (10 mL) were added. The resulting solution was stirred for 2 h at room temperature, dissolved in acetone (2 x 200 mL) and filtered. The filtrate was concentrated under reduced pressure to provide 1.40 g (75% yield) of potassium ((5-(tert- butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(lH)-yl)methyl)trifluoroborate as a yellow solid. LCMS (ESI, m/z): 293 [M-K]”.

According to the analysis of related databases, 141449-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WIENER, John J. M.; WEBER, Olivia D.; DUNCAN, Katharine K.; (364 pag.)WO2018/217805; (2018); A1;,
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Electric Literature of 19982-07-1, 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. 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

l-Acetamido-3,5-dimethyladamantane (44 gm) as obtained in example 1, sodium hydroxide and diethylene glycol are added, and heated to reflux. Then, the contents were maintained for 6 hours at reflux and water (1 175 ml) was added under stirring. The reaction mass was cooled to below 20 C and then added methylene chloride (750 ml), and stirred for 15 minutes at 20C. The layers were separated and the organic layer was distilled off completely under vacuum at below 45C to obtain a residue. The residue was dissolved in ethyl acetate (700 ml). Ethyl acetate hydrochloride (160 ml) was added to the reaction mass and stirred for 5 hours at 25 to 30C. The reaction mass was cooled to 0 to 5C and stirred for 1 hour at 0 to 5 C. The separated solid was filtered and dried at 50C for 2 hours to obtain 87 gm of memantine hydrochloride containing l-amino-3,5,7-trimethyladamantane hydrochloride and l-amino-3-methyladamantane hydrochloride impurity.Memantine hydrochloride: 99.3%;The combined contents of l-amino-3,5,7-trimethyladamantane hydrochloride and 1- amino-3-methyladamantane hydrochloride impurity: 0.5%.

The chemical industry reduces the impact on the environment during synthesis N-(3,5-Dimethyladamantan-1-yl)acetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; RAJI REDDY, Rapolu; RAMAKRISHNA REDDY, Matta; VAMSI KRISHNA, Bandi; WO2011/125062; (2011); A1;,
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These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)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. category: amides-buliding-blocks

86.63 mg diphenyl cyanocarbonimidate, 52.1 mg isoquinolin-6-amine, and 6 ml THF were added to a reaction bottle with thermal reflux for 3.5 hrs. After removing THF by vacuum, the residue was added to 10 ml EA. The precipitated solid was filtered to obtain 32.9 mg 1-cyano-3-(isoquinolin-6-yl)-2-phenylisourea. The intermediate was reacted with equivalent tert-butyl-2-(benzylamino)ethylcarbamate and 20 mg of DIPEA in 5 ml DMF at 110 C. for 18 hrs. After cooling, 1N NaOH was added and extracted twice with EA. After the combined EA layer was dried and concentrated by Na2SO4, 26.4 mg intermediate product was eluted out by a SiO2 column (EA/Hexane 4:1). The intermediate was added to 1.5 ml 6N HCl at room temperature with stirring overnight. After the reaction solution was evaporated under reduced pressure, 2 ml acetone/methanol (10:1) was added. The precipitate was filtered and washed with acetone, and then the solid was taken and evaporated in vacuum to give 18.7 mg of product.

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Industrial Technology Research Institute; CHEN, Chih-Hung; CHEN, Yi-Hsun; HUANG, Jui-Wen; HUANG, Kuo-Kuei; LIU, Chih-Peng; HWANG, Chrong-Shiong; (22 pag.)US2019/194137; (2019); A1;,
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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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 53844-02-3

Step 2 Synthesis of 3-(2-aminoethoxy)benzonitrile hydrobromide: 8 g of benzyl-N-(2-bromoethyl)carbamate, 3.7 g of 3-hydroxybenzonitrile, 4.3 g of calcium carbonate, 5.1 g of potassium iodide and 1.1 g of tetrabutylammonium iodide were stirred in dimethylformamide at 60C. After the treatment with ethyl acetate as the extractant in an ordinary manner, the product was purified by the silica gel column chromatography to obtain 3-[2-(benzyloxycarbonylamino)ethoxy]benzonitrile.

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ajinomoto Co., Inc.; EP976722; (2000); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics