Tag: M.W=100-200

Reference of 122334-37-6, These common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, 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.

Example 1; 3-(4-chloro-phenyl)-2-(2>4-dichloro-phenyl)-4,5,6,7-tetraliydro-2H- indazole-7-carboxylic acidpiperidin-1-ylamide (Cpd 33); To a solution of LHMDS (21 mL, 2.1 mmol) in 50 mL of anhydrous THF under a nitrogen atmosphere at -78 0C was added 2-oxo-cyclohexanecarboxylic acid ethyl ester Compound Ia (1.80 g, 10.0 mmol) in 10 mL of anhydrous THF. The resultant homogeneous mixture was left to stir at -78 0C for 40 min followed by the drop wise addition of 4-chloro-N-methoxy-N-methyl-benzamide Compound Ib (2.0 g, 10 mmol) in 10 mL of anhydrous THF. The reaction mixture was allowed to stir for 18 hours and allowed to warm to ambient temperature. The reaction mixture was quenched with water (50 mL) and the organic layer was extracted with EtOAc (200 mL) and washed with brine, separated and dried with anhydrous Na2SO4, then filtered and concentrated in vacuo to yield 3-(4-chloro-benzoyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester Compound Ic (1.7 g) as an oil, which was used in the next step without further purification.

Statistics shows that 4-Chloro-N-methoxy-N-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 122334-37-6.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; WO2007/95513; (2007); 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. 579-10-2, name is N-Methylacetanilide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-Methylacetanilide

A solution of N-methyl-N-phenylacetamide (73.8 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 5 C. and the resulting solution was allowed to warm to rt and was maintained 16 h. The reaction mixture was diluted with iced water (100 mL) and was extracted with dichloromethane (2*50 mL). The combined organic layers were dried (sodium sulfate) and concentrated. The residue was purified by Flash chromatography (10/1 ethyl acetate/petroleum ether) to give 4-(N-methylacetamido)benzene-1-sulfonyl chloride in 11% yield as a white solid. Data: 1H NMR (CDCl3) delta 8.09 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.17 (s, 3H).

The synthetic route of 579-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/22581; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Isopropylmagnesium chloride (2 M in THF, 7.63 mL, 15.26 mmol) was added dropwise to a solution of 3-(benzyloxy)-5-bromopyridine (3.10 g, 1 1.74 mmol) in THF (20 mL) at 0 ¡ãC. The mixture was stirred at rt for 90 min and a solution of 2-chloro-A/-methoxy-/V-methyl- acetamide (1.78 g, 12.9 mmol) in THF (20 mL) was added dropwise. The mixure was stirred at rt for 1 h. NH4CI (aq, 10 percent) was added and the mixture was extracted with Et20. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The residue was purified by chromatography to give the sub-title compound (1.00 g, 3.82 mmol, 33 percent).

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; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); 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. 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (3-hydroxycyclobutyl)carbamate

Step B: Tert-butyl 3-fluorocyclobutylcarbamate. To a solution tert-butyl 3-hydroxycyclobutyl – carbamate ( 1 g, 5.35 mmol) in dry DCM (20 mL) at -70 C was added DAST dropwise (l g, 0.85 mL, 1 .17 eq) under the atmosphere of N2. The mixture was then slowly warmed to room temperature and stirred overnight. The resulting mixture was washed with diluted aq. NaHC03. The organic layer was dried over anhydrous Mg2S04 and concentrated. The residue was purified by flash chromatography using petroleum ether / EtOAc (V:V, 20: 1 to 2: 1 ) as eluent to afford a white solid as the desired product. MS : 190.1 (M+ l )+.

The synthetic route of 154748-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Amide – Wikipedia,
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Synthetic Route of 627-12-3, 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. 627-12-3, name is Propyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, Propyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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Some common heterocyclic compound, 84713-20-2, name is Benzyl vinylcarbamate, molecular formula is C10H11NO2, 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. Recommanded Product: Benzyl vinylcarbamate

EXAMPLE 3 cis-(2-Ethyl-6-trifluoromethyl-1 2,3,4-tetrahydro-quinolin-4-yl)-carbamic Acid Benzyl Ester A one liter, four neck flask under nitrogen atmosphere was charged with N-vinyl-carbamic acid benzyl ester (27.66 g, 156 mmol, 1.0 equiv) and dry toluene (500 mL). (1-Benzotriazol-1-yl-propyl)-(4-trifluoromethyl-phenyl)-amine (50.0 g, 156 mmol, 1.0 equiv) and p-toluenesulfonic acid monohydrate (297 mg, 1.56 mmol, 0.01 equiv) were added, and the mixture heated to 70 C. After 2 h, the mixture was cooled to room temperature and transfered to a separatory funnel. Ethyl acetate (500 mL) was added. The mixture was washed 1*200 mL 1N NaOH, 1*200 mL H2O, 1*200 mL brine, and dried (MgSO4). The mixture was filtered and the solids washed 1*50 mL ethyl acetate. The filtrate was concentrated to approximately 250 mL. 500 mL toluene were added, and the mixture concentrated to approximately 500 mL. 500 mL n-heptane were added, the slurry was stirred 1 h, filtered through a Buchner funnel, and dried. cis-(2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester was isolated as a white powder (45.04 g, 76%): mp 155-157 C.; 1H NMR (DMSO-d6, 400 MHz) delta 0.92 (t, 3H, J=7.5 Hz), 1.5 (m, 3H), 2.00 (m, 1H), 3.35 (m, 1H), 4.77 (m, 1H), 5.07 (d, 1H, J=12.5 Hz), 5.15 (d, 1H, J=12.5 Hz), 6.35 (s, 1H), 6.61 (d, 1H, J=8.5 Hz), 7.12 (s, 1H), 7.18 (dd, 1H, J=1.9, 8.5 Hz), 7.4 (m, 5H), 7.70 (d, 1H, J=9.1 Hz); 13C NMR (DMSO-d6, 100 MHz) delta 157.03, 149.02, 137.79, 128.82, 128.23, 128.03, 125.9 (q, J=270 Hz), 125.06, 123.50, 121.73, 115.2 (q, J=31.7 Hz), 113.33, 65.85, 52.09, 47.83, 34.02, 28.68, 9.93; DEPT spectrum: quaternary carbons delta 157.03, 149.02, 137.79, 125.9, 121.73, 115.2; CH carbons delta 128.82, 128.23, 128.03, 125.06, 123.50, 113.33, 52.09, 47.83; CH2 carbons delta 65.85, 34.02, 28.68; CH3 carbon delta 9.93; IR (drifts) 3430 (m), 3303 (s), 2951 (m), 1686 (vs), 1542 (vs), 1088 (vs); MS (APCI+) m/z (rel. intensity) 379 (M+H+, 53), 228 (100); Anal. Calcd for C20H21N2O2F3: C, 63.48; H, 5.59; N, 7.40; Found: C, 63.69; H, 6.06, N, 7.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84713-20-2, its application will become more common.

Reference:
Patent; Shear, Charles L.; US2002/35125; (2002); 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. 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, A new synthetic method of this compound is introduced below., name: 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide

Add dU-I (0.7mmol, 247mg) to a single-mouth bottle, add 9.7mg CuI and 20.3mg Pd(PPh3)4 to the reaction flask, vacuum, protect with nitrogen, wrap with aluminum foil, add 2.3ml DMF, stir and dissolve. 0.2 ml of TEA was added, and trifluoroethylpropynylamine (254 mg, 1.7 mmol) was weighed and dissolved in DMF, and then added to the above reaction flask, stirred at room temperature, and allowed to react overnight. After the reaction is completed, the solvent is evaporated to dryness under reduced pressure, and then directly separated by column chromatography, and dichloromethane and methanol are mixed at a volume ratio of 20:1 as a leaching agent to obtain dU-F3.

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; Suzhou Bai Yuan Genes Co., Ltd.; Lanzhou Bai Yuan Genes Co., Ltd.; Che Tuanjie; (40 pag.)CN108752406; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 2895-21-8, These common heterocyclic compound, 2895-21-8, name is N-Isopropyl-2-chloroacetamide, 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-chloro-N-isopropylacetamide (201 mg, 1.48 mmol) in ethanol (1.73 mL) was added 4-bromo-o-anisidine (300 mg, 1.48 mmol) and potassium carbonate (615 mg, 4.45 mmol). The reaction mixture was then allowed to stir at 80 C overnight. The reaction was cooled to r.t. and concentrated under reduced pressure. The residue was taken up in EtOAc, and washed with NaOH (4.0 M). The aqueous layer was extracted with EtOAc (x3), the organic layers combined, washed with saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography eluting with 30-50% acetonitrile (0.1% formic acid additive) in water (0.1% formic acid additive) to yield 2-(4-bromo-2-methoxy-anilino)-N-isopropylacetamide (110 mg, 0.36 mmol, 25% yield) as a white solid. UPLC-MS (ES+, Method A): 1.65 min, m/z 301.2 [M+H]+.1H NMR (400 MHz, CDCl3) delta6.98 (dd, J = 8.3, 2.7 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.47-6.41 (m, 1H), 6.34 (d, J = 8.3 Hz, 1H), 4.18-4.08 (m, 1H), 3.87 (s, 3H), 3.73 (s, 2H), 1.11 (d, J = 6.6 Hz, 6H).

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

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;,
Amide – Wikipedia,
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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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C8H17NO3

(1) t-Butyl (2-hydroxyethyl)methylcarbamate (1.0 g) obtained by the method described in the literature (Synthetic Communications, 1993, p.2443) was dissolved in chloroform (5 ml), and a Dess-Martin reagent (2.54 g) was added to the solution under ice cooling. The resulting mixture was stirred at room temperature for 1.5 hours, then saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate were added to the reaction mixture, and the resulting mixture was stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain an aldehyde compound (1.21 g).

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; Taisho Pharmaceutical Co., Ltd.; Meiji Seika Kaisha, Ltd.; EP2287173; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4563-33-1, name is Phenylmethanesulfonamide, 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 4563-33-1, COA of Formula: C7H9NO2S

(b) tert-Butyl 3-[(benzylsuIfonyI)carbamoyl]azetidine-l-carboxylateTBTU (33.71 g, 105 mmol) and TEA (30.3 g, 300 mmol) was added to a solution of 1- (tert-butoxycarbonyl)azetidine-3-carboxylic acid from above (25.89 g, assumed to contain is 100 mmol) in THF (200 mL) and the reaction was stirred at r.t for 30 minutes. 1- phenylmethanesulfonamide (17.97 g, 105 mmol) and LiCl (1.844 g, 43.5 mmol) was added and the stirring was continued at r.t over night (23 hours). The reaction was concentrated to about 1/3 was left and EtOAc (500 mL) was added and the organic phase was washed with 2 M HCl (1 x 150 mL, 2 x 50 mL), water (2 x 50 mL). Drying (MgSO4), filtration and20 evaporation of the solvent gave a brown powder (48. 6 g). The powder was slurried in 150 mL TBME and stirred 3 hours. The solids was filtered off and washed with TBME (40 mL). This procedure was repeated twice with 100 mL TBME (washing with 25 mL) to give a brownish powder (33 g) still containing some HOBT. The powder was dissolved in about 100 mL warm EtOH and water (130 mL) was added to induce a crystallisation of the25 product. The crystals was filtered off and dried to give pure tert-butyl 3-[(benzylsulfonyl)carbamoyl]azetidine-l-carboxylate as an off white powder. Yield: 25.4 g(71%).1H NMR (400 MHz, DMSO-d6) delta 1.39 (9H, s), 3.30 (IH, m, overlapping with the watersignal in DMSO), 3.78-3.95 (4H, m), 4.73 (2H, s), 7.28-7.34 (2H, m), 7.36-7.41 (3H,30 m), 11.71 (IH, br s). MS m/z: 353 (M-I).

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, Phenylmethanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/4946; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics