Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 676371-64-5, name is Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, 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 676371-64-5, Recommanded Product: 676371-64-5

To a stirring solution of methyl 3-((tert- butoxycarbonyl)amino)bicyclo[1 .1 1 ]pentane-1 -carboxylate (0.2 g, 0.829 mmol) in THF (3.0 ml_), under nitrogen, in an ice bath was slowly added methylmagnesium bromide (3 M in Et20, 5 ml_, 3.32 mmol). After addition, the reaction mixture was stirred in the ice bath for ~10 min and then at rt for ~30 mins. The reaction was quenched with sat. aq. ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude tert- butyl (3-(2-hydroxypropan-2-yl)bicyclo[1 .1 1 ]pentan-1 -yl)carbamate (187 mg, 0.775 mmol, 93 % yield) as a colorless oil. 1H NMR (400 MHz, CD3SOCD3) d ppm 7.39 (br. s., 1 H), 4.1 1 (s, 1 H), 1 .70 (s, 6 H), 1 .37 (s, 9 H), 1 .03 (s, 6 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, Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; CADILLA, Rodolfo; (152 pag.)WO2019/116256; (2019); A1;,
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Some common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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: C12H18N2O2

Solution of DA-171 (189 mg, 1 mmol) and tert-butyl 3-aminobenzylcarbamate (222 mg, 1 mmol) in MeOH (10 mL) was stirred for 2 days. Solvent was removed in vacuo and residue was purified by MPLC (silica, 0-10% MeOH in DCM) to give white solid of DA-76. DA-76 (382 mg, 0.928 mmol) was dissolved in MeOH saturated with HCI (5 mL). Clear solution was stirred for 2 h and then diluted with diethyl ether. Formed crystals were filtered off, washed with ether and dried in vacuo to give white powder of DA-87. To a solution of DA-87 (50 mg, 0.130 mmol) and 3-phenylpropiolic acid (21 mg, 0.143 mmol) in DMF (3 mL) TEA (66 mg, 0.650 mmol) followed by PPA (50% solution in AcOEt, 99 mg, 0.156 mmol) was added. Deep red solution was stirred overnight, diluted with AcOEt, washed 3x with brine, dried with sodium sulfate and the solvent was removed in vacuo to give pale yellow thick oil. It was purified by MPLC (silica, 0-10% MeOH in DCM) to give colorless glass.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147291-66-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret; WO2013/62945; (2013); 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. 16313-66-9, name is 2-Amino-5-bromobenzamide, A new synthetic method of this compound is introduced below., Formula: C7H7BrN2O

General procedure: To a solution of 2-aminobenzamide 1 (0.24 mmol, 1 equiv) and 2-alkynylbenzaldehyde 2 (0.24 mmol, 1 equiv) in DMSO (4 mL) was added AgNO3 (8 mg, 20 mol%). The resulting mixture was then heated at 120 C for 4 h. After completion of the reaction, the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by chromatography (silica gel, acetone/hexane 20:80) to afford the product.

The synthetic route of 16313-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sonawane, Amol D.; Shaikh, Yunnus B.; Garud, Dinesh R.; Koketsu, Mamoru; Synthesis; vol. 51; 2; (2019); p. 500 – 507;,
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Electric Literature of 263349-73-1, 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 263349-73-1 as follows.

EXAMPLE 342: 3-fluoro-4-(6-(trifluoromethyl)-lH-indazol-4- yl)benzenesulfonamide [0976] To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-lH-indazole (40 mg, 0.128 mmol), 4-bromo-3- fluorobenzenesulfonamide (39.1 mg, 0.154 mmol), aqueous saturated sodium bicarbonate (0.274 mL, 0.513 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), and dioxane (2 mL) to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140C for 30 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (13.7 mg, 22.6%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.50 (s, 2 H), 7.53 (s, 1 H), 7.75-7.80 (m, 1 H), 7.92-7.94 (m, 1 H), 8.02 (s, 1 H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1 H), 8.40 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F4N302S, 360.0; found 360.1. According to the analysis of related databases, 263349-73-1, the application of this compound in the production field has become more and more popular. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
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Electric Literature of 830-43-3, The chemical industry reduces the impact on the environment during synthesis 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of l-[3-cyano-5-(isopropoxycarbonyl)-6-methylrhoyridin-2-yl]azetidine-3- carboxylic acid (0.091 g, 0.3 mmol), DIPEA 0.074 g, 0.6 mmol) and TBTU (0.039 g, 0.3 mmol) in leq. DCM/ 1 eq .DMF (2 mL) was added to sulfonamide^ .4 mmol), e.g. 4- (trifluoromethyl)benzenesulfonamide. The reaction mixture was stirred for 48h followed by addition of TBTU (0.013 g, 0.1 mmol). After 2Oh the solvents were removed in vacuo. The crude reaction mixture was added NaHSO4 (2 mL, IM) and due to differences in solubility between products DCM and DCM/ethyl acetate was used for extraction. The organic phase was isolated and the solvents were removed in vacuo. The crude material was purified using preparative HPLC (see below for details) in order to isolate the desired product, e.g. isopropyl 5-cyano-2-methyl-6- {3-[({ [4-(trifiuoromethyl)phenyl]sulfonyl}amino)carbonyl]azetidin- 1 – yl}nicotinate.

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, 4-(Trifluoromethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2007/8140; (2007); A1;,
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. 3792-04-9, name is 2-Chloro-N-(2-(trifluoromethyl)phenyl)acetamide, A new synthetic method of this compound is introduced below., Formula: C9H7ClF3NO

Chrysin (1) (100 mg, 0.39 mmol), 2-chloro-N-(2-(trifluoromethyl)phenyl)acetamide (6) (98 mg,0.41 mmol) and anhydrous potassium carbonate (112 mg, 0.81 mmol) were dissolved in DMF (4 mL).The reaction mixture was stirred at 75 C for 9 h, then, it was poured into water (30 mL). Afterfiltering off the precipitate, the filtrate was diluted with saturated NaCl solution (30 mL) andextracted with DCM (4 x 30 mL). The combined organic layer was washed with water (30 mL), driedover MgSO4 and concentrated in vacuo. The filtered precipitation and the crude product obtained byextraction were purified separately with preparative TLC (DCM : MeOH = 60 : 1). Combining thepure products 50 mg (28 %) of compound 20 was isolated as a white solid. M.p.: 210-212 C. TLC(DCM : MeOH = 60 : 1); Rf = 0.71.

The synthetic route of 3792-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mayer, Szabolcs; Keglevich, Peter; Abranyi-Balogh, Peter; Szigetvari, Aron; Dekany, Miklos; Szantay, Csaba; Hazai, Laszlo; Molecules; vol. 25; 4; (2020);,
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These common heterocyclic compound, 127033-74-3, name is N-(3-Methoxyphenyl)cinnamamide, 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. SDS of cas: 127033-74-3

In a 1000 mL reaction flask, 60 g of N- (cinnamoyl) -3-methoxyaniline was charged,100 g of anhydrous aluminum trichloride,500 mL of anhydrous chlorobenzene,Heating to 120 ,After refluxing for 2 hours,The reaction solution was poured into 500 mL of ice water,Produce a lot of hydrochloric acid gas,After stirring for 2 hours,The filter cake was added to 500 mL of methanol to recrystallize,To give 39 g of a light red solid,Yield: 60%Purity 94.5%.

The synthetic route of N-(3-Methoxyphenyl)cinnamamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Nuoxing Pharmaceutical Technology Co., Ltd.; Jiang Kaiyuan; Zheng Zhiwei; Sun Weihong; (6 pag.)CN107098855; (2017); A;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 610302-03-9, 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 610302-03-9 as follows.

Step B – Synthesis of Intermediate Compound 6c To a solution of compound 6b (4.1 mg, 19.04 mmol), 4-nitrobenzoic acid (3.82 g, 22.85 mmol), and PPh3 (9.9g, 38.1 mmol) in THF (60 ml) was added DEAD (6.03 mL, 38.1 mmol) at 0C. The reaction mixture was then stirred at 25C for 16 h, quenched with water (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic phase was washed with water (100 mL x 2), dried over Na2S04, and concentrated in vacuo. The residue was purified using column chromatography (Si02, Petroleum ether: EtOAc = 10: 1 to 5: 1) to provide compound 6c (1.3 g, 81% yield) as a white solid.

According to the analysis of related databases, 610302-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; NEELAMKAVIL, Santhosh F.; WALJI, Abbas; MARCO, Christine Ng Di; COLEMAN, Paul; WAI, John; RAHEEM, Izzat T.; HU, Lihong; PENG, Xuanjia; WO2015/39348; (2015); A1;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 109903-35-7, 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. 109903-35-7 name is 4-Amino-N-methylbenzenemethanesulfonamide, 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.

Example 23: 1-(4-{[5-acetyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)- ylidene]amino}phenyl)-lambda/-methylmethanesulfonamide hydrochloride; A mixture of 4-amino-N-methyl-alpha-toluenesulphonamide (200mg, I .Ommol), ethyl isothiocycanate (104mg, 1.20mmol, 0.1 ml) and triethylamine (0.2ml) in ethanol (5ml) was stirred at reflux for 2 hours. The solvent was then removed by rotary evaporation, the resulting material was then suspended in toluene (5ml) and treated with 3-chloro-2,4- pentanedione (0.14g, 1.05mmol, 0.13ml) and the whole mix stirred at 9O0C (oil bath temperature) for 3 hours, and allowed to cool. The reaction mix was filtered and the filtrate evaporated under reduced pressure to give a yellow oil, which was purified by MDAP (mass directed auto-preparation). The relevant fractions were combined and the solvent removed by rotary evaporation to give a brown oil, which was dissolved in dichloromethane (1 ml) and treated with 1 M ethereal HCI (1 ml). The solvent was removed by air drying. The product was triturated in ether, the liquid was decanted off and the residual material was vacuum oven dried to give the title compound as a beige coloured solid (98mg, 24%).LC/MS (ES): Found 368 (ES+), retention time 2.35mins. Ci6H2IN3O3S2 requires 367. 1 H-NMR (400MHz, MeOD-d4): delta 1.49 (3H, t, J=7Hz), 2.52 (3H, s), 2.71 (3H, s), 2.76 (3H, s), 4.31 (2H, m), 4.42 (2H, s), 7.55 (2H, m), 7.66 (2H, d, J=8Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-methylbenzenemethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53448; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

A round-bottom flask was charged with triphosgene (1.68 g, 5.66 mmol) and DCM (200 mL). Hexafluoroisopropanol (1.93 mL, 18.4 mmol) was added dropwise over 1 min. DIPEA(4.9 mL, 28.0 mmol) was added dropwise over 3 min. The flask contents were stirred at rt for 2 h. tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3.00 g, 14.2 mmol) was added in one portion, and the reaction mixture was allowed to stir for 18 h at rt. The reaction mixture was then washed with 1 N HCl and brine. The organics were dried over anhydrous NazS04 and concentrated. The resulting oil was chromatographed on a silica column with a gradient (100% hexanes to 80% hexanes/20% acetone) to provide 2-tert-butyl5-(1,1,1,3,3,3-hexafluoropropan-2-yl) tetrahydropyrrolo[3,4-c]pyrrole-2,5(1H,3H)-dicarboxylate (5.74 g, 82%). 1H NMR (400 MHz,Chloroform-d) 0 5.87-5.66 (m, 1H), 3.85-3.70 (m, 2H), 3.70-3.55 (m, 2H), 3.46-3.37 (m,2H), 3.37- 3.17 (m, 2H), 2.96 (br s, 2H), 1.52 (s, 9H). ). LCMS (ESI, m/z): 429.0 [M+Ht.

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; JONES, Todd, K.; CISAR, Justin, S.; GRICE, Cheryl, A.; WANG, Dong-Hui; WEBER, Olivia, D.; WO2015/3002; (2015); A1;,
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