Tag: M.W=100-200

Synthetic Route of 64214-66-0, 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 64214-66-0 as follows.

3-Chloropropyl 3,5-dimethylphenyl ketone A solution of 10.2 mL (13.9 g; 72 mmol) 5-bromo-m-xylene in 200 mL of anhydrous tetrahydrofuran was stirred under nitrogen at -78 C. as 35.8 mL (84 mmol) of 2.5M n-butyllithium in tetrahydrofuran was added dropwise. After 15 minutes at -78 C., a solution of 10.0 g (60 mmol) of 4-chloro-N-methoxy-N-methylbutyramide in 30 mL of anhydrous tetrahydrofuran was added dropwise over 25-30 minutes. The resulting solution was maintained at -78 C. for 45 minutes and then warmed briefly to room temperature. The reaction was quenched by addition of 40 mL of 2N hydrochloric acid and then partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and then saturated aqueous sodium chloride solution. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue afforded 8.91 g (70%) of an oil, which had satisfactory purity by 1 H NMR (CDCl3).

According to the analysis of related databases, 64214-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US6156767; (2000); A;,
Amide – Wikipedia,
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Synthetic Route of 3984-14-3, A common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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.

To a solution of 2,4,5-trifluorobenzoic acid (5 g, 28.4 mmol) in dichloromethane (50 ml_) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.53 g, 42.6 mmol) and triethylamine (8.64 g, 1 1 .9 ml_, 85.2 mmol). After 15 minutes N,N-dimethylsulfamide (5.3 g, 56.8 mmol) was added followed by 4-dimethylaminopyridine (347 mg, 2.8 mmol). The resulting mixture was allowed to stir at room temperature for 18 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate (50 ml_) and 2M HCI (150 ml_). The aqueous phase was separated and extracted with ethyl acetate (2 x 50 ml_). The combined organic extracts were dried over magnesium sulfate, filtered, evaporated and the residue purified by reverse-phase chromatography using a gradient of acetonitrile + 0.1 % formic acid to 100% acetonitrile to yield the title compound (993 mg, 31 %) as a white solid. 1H NMR (400 MHz, CDCI3): delta 3.02 (s, 6H), 7.08 (dd, 1 H), 7.92 (dd, 1 H), 8.60-8.80 (br s, 1 H). LCMS Rt = 2.60 minutes MS m/z 281 [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; PFIZER LIMITED; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2013/88315; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2-chloro-N-isopropylacetamide (602 mg, 4.44 mmol) and methyl 4-hydroxybenzoate (500 mg, 3.29 mmol) in DMF (18 mL) at r.t. under N2 was added potassium carbonate (1817 mg, 13.15 mmol) in a single portion. The mixture was heated at 80 ^C overnight, cooled and partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organics were washed with H2O and brine, dried (phase sep.) and concentrated to give crude methyl 4-[2-(isopropylamino)-2-oxo- ethoxy]benzoate (870 mg, 3.18 mmol, 97% yield). LC-MS (ES+, Method C): 2.32 min, m/z 252.0 [M+H]+

The chemical industry reduces the impact on the environment during synthesis N-Isopropyl-2-chloroacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
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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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1,4-Diazepan-1-yl)ethanone

A solution of lambda/-(7-chloro-2-methylpyrazolo[l,5-alpha]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol) and l-(l,4-diazepan-l-yl)ethanone (101 mg, 0.75 mmol) in DMF (1.0 mL) was stirred at 100 0C for 2h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (25-40% MeCN/H2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (87.7 mg, 78%). 1H NMR (DMSO-de) [1 :1 ratio of rotamers: delta: 10.93 (s, IH); 10.91 (s, IH)], 7.99 (d, J = 8.3 Hz, 2H), 7.62 (dd, 2H), [1 :1 ratio of rotamers: 7.13 (s, IH); 7.07 (s, IH)], [1 :1 ratio of rotamers: 6.19 (s, IH); 6.18 (s, IH)], [1 :1 ratio of rotamers: 4.37 (t, J = 5.6 Hz, 2H); 4.20 (t, J = 5.4 Hz, 2H)], [1 :1 ratio of rotamers: 4.03 (t, J = 5.6 Hz, 2H); 3.97 (t, J = 5.9 Hz, 2H)], 3.63 – 3.78 (m, 2H), [1 :1 ratio of rotamers: 3.58 (t, J = 5.9 Hz, 2H); 3.52 (t, J = 5.8 Hz, 2H)], 2.37 (s, 3H), [1 :1 ratio of rotamers: 2.03 – 2.11 (m, 2H); 1.94 (quin, J = 5.9 Hz, 2H)], [1 :1 ratio of rotamers: 2.02 (s, 3H); 1.89 (s, 3H)], 1.46 (s, 6H); ESI-MS: m/z 451.3 (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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/123986; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 20188-40-3, A common heterocyclic compound, 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, molecular formula is C8H11ClN2O, 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.

To a solution of ethyl 2-(bromomethyl)-6-(2-fluoro-4-(trifluoromethyl)phenoxy)benzoate (0.21 g) obtained in Reference Example 328 in ethanol (2 mL) were added 4-(aminomethyl)benzamide hydrochloride (0.11 g) and potassium carbonate (0.14 g), and the mixture was stirred at 45°C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and the obtained solid was recrystallized from ethyl acetate-ethanol. The obtained crystals were collected by filtration and dried to give the title compound (0.055 g). MS: [M+H]+ 445.1 1H NMR (300 MHz, DMSO-d6) delta 4.42 (2H, s), 4.68 (2H, s), 7.04 (1H, t, J = 8.4 Hz), 7.15 (1H, d, J = 7.9 Hz), 7.31 (3H, d, J = 8.1 Hz), 7.46 (1H, d, J = 7.6 Hz), 7.51 (1H, d, J = 8.5 Hz), 7.62-7.69 (1H, m), 7.81-7.96 (4H, m).

The synthetic route of 20188-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); 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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

The N – (4 – fluoro -2 – methoxy -5 – nitro – phenyl) -4 – (6 – methoxy -1 – methyl – 1H – indole -3 – yl) pyrimidine -2 – amine (3 d) (0.42 g, 1.0 mmol) dissolved in tetrahydrofuran (30 ml), is added sodium hydride (0.04 g, 2.0 mmol, w/w=60%), stir at room temperature 30 minutes, add (1 – hydroxy methyl propyl) – tert-butoxycarbonyl amino (0.23 g, 1.5 mmol), continuing stirring at room temperature 5 hours. The addition of water (10 ml) quenching the reaction, concentrated under reduced pressure to remove most of the tetrahydrofuran, is added to the residue in methylene chloride (100 ml), water (50 ml), layered, aqueous phase methylene chloride (100 ml) extraction, the combined organic phase, saturated salt water (50 ml) washing, drying with anhydrous sodium sulfate, concentrated under reduced pressure, to obtain a yellow solid N – [1 – [[5 – methoxy -4 – [[4 – (6 – methoxy -1 – methyl – indole -3 – yl) pyrimidine -2 – yl] amino] -2 – nitro – phenoxy] methyl] cyclopropane alkyl] tert-butyl carbamate (3 e) (0.59 g).

According to the analysis of related databases, 107017-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Li Yao; Zhang Guobiao; Hu Shihong; Wei Yonggang; (22 pag.)CN108530428; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

758-96-3, name is N,N-Dimethylpropionamide, 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. Application In Synthesis of N,N-Dimethylpropionamide

Scheme AStep a1a: compound A2 (N,N-2-trimethyl-3-oxopentanamide)32.1 ml (0.35 mol) phosphoryl trichloride (POCI3) were dissolved in 100 mL of toluene. 32.6 ml (0.3 mol) A , V-dimethylpropionamide (A1) (dissolved in 50 mL toluene) were added to the resulting solution under stirring under an inert gas atmosphere. The reaction mixture was heated to 80C for 6 h, allowed to cool to RT and stirred for another 12 h at RT. After evaporation of toluene under reduced pressure, the resulting mixture was stirred for 2 h. 100 mL toluene were then added, the resulting mixture was cooled to below 0C and icy water (100 mL) was added. Then, 24 g of solid NaOH, dissolved in water, were added to the mixture. After 1 h of stirring, 47.7 g Na2C03 as solid were added and the resulting mixture was stirred for 16 h at RT. The organic layer was separated, dried over MgS04 and distilled (0.8 bar, 78-82C). 10.8 g (46%) of A2 was obtained in form of a colorless solid.

The synthetic route of 758-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; BUSCHMANN, Helmut, Heinrich; HOLENZ, Joerg; WO2011/157390; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 5238-56-2, 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. 5238-56-2 name is N-(2-Hydroxyethyl)methacrylamide, 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 glycosyl donor10 1 (0.635 gm, 1 mmol), glycosyl acceptor 10b (0.142 g 1.1 mmol) and 4 A molecular sieves powder (100 mg) in anhydrous CH2Cl2 (10 mL) was added AuBr3 (0.031 g, 0.07 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for the specified time and the completion of the reaction is judged by TLC analysis. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to obtain a crude residue which was purified by conventional silica gel column chromatography using ethyl acetate-petroleum ether as mobile phase to obtain compound 11b.

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

Reference:
Article; Thadke, Shivaji A.; Kar, Mritunjoy; Gupta, Sayam Sen; Hotha, Srinivas; Carbohydrate Research; vol. 346; 12; (2011); p. 1511 – 1518;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 107017-73-2,Some common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, molecular formula is C9H17NO3, 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.

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate 6a (92 mg, 0.49 mmol) was placed in a reaction flask, followed by addition of 4-(3-(6-hydroxypyridin-3-yl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 10c (100 mg, 0.24 mmol), triphenylphosphine (97 mg, 0.37 mmol), 5 mL of dichloromethane, and diisopropyl azodicarboxylate (75 mg, 0.37 mmol), successively. The reaction solution was stirred for 2 hours. The reaction solution was purified by thin layer chromatography with elution system A, and subsequently with elution system B to obtain the title compound tert-butyl (1-(((5-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)pyridin-2-yl)oxy)methyl)cyclopropyl)carbamate 11a (40 mg, yield 28.4%) as a white solid. MS m/z (ESI): 576.2 [M+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 (1-(hydroxymethyl)cyclopropyl)carbamate, its application will become more common.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Medicine Co., Ltd.; Lu, Hejun; Sun, Piaoyang; Fei, Hongbo; Jiang, Hongjian; Wang, Haowei; Dong, Qing; US2015/225381; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 24243-71-8, name is Propane-1-sulfonamide, 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. HPLC of Formula: C3H9NO2S

A mixture of 5-(6-chloro-2-phenylpyrimidin-4-yl)-1,3-dimethylpyridin-2(1H)-one (51 mg, 0.2 mmol), propane-1-sulfonamide (37 mg, 0.3mmo1), Pd(dba)3 (18 mg, 0.02 mmol), Xphos (9 mg, 0.2 mmol), CsCO3 (130 mg, 0.4 mmol) in dioxane (3 mL) was stirred and heated at 90 C. for 16 hr. The reaction mixture was diluted with water and extracted with EtOAc (3*). The extracts were combined, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EA:Hex, 0-100%) to provide the 16 mg (23%) of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.99 (t, J=7.45 Hz, 3H) 1.78 (sxt, J=7.38 Hz, 2H) 2.14 (s, 3H) 3.32 (s, 3H) 3.62 (s, 3H) 3.63-3.69 (m, 2H) 7.06 (s, 1H) 7.51-7.59 (m, 3H) 7.99 (s, 1H) 8.41-8.52 (m, 2H) 8.64 (d, J=2.27 Hz, 1H) 11.26 (br. s., 1H).

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

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics