Tag: M.W=100-200

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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl methylcarbamate

2-Bromo-5-hydroxy-6-nitropyridine (132.8 g, 0.606 mol), cesium carbonate (594.7 g,1.83 mol), tert-butyl methylcarbamate (116.7 g, 0.890 mol) and anhydrous DMF (4.0 L) were combined and the resultant orange mixture was sparged with nitrogen for 10 minutes. Xantphos (53.1 g, 0.0918 mol) and palladium acetate (13.5 g, 0.0601 mol) were then added and the solution was heated to 80C with continuous nitrogen gas sparging for 3 days. The mixture was allowed to cool and stir overnight. 2-Methyltetrahydrofuran (MeTHF, 4.OL) wasadded and the resultant slurry was stirred for 2.5 hours and then filtered through Celite. Thefilter cake was washed with 2 x 1.0 L of MeTHF. The filtrate was then partitioned with 8.0 Lof water. The organic layer was discarded and the aqueous layer acidified to pH 1-2 with 60mL of 12N HC1. Ethyl acetate (4.0 L) was added and the layers were separated. The organic layer was washed with water (2.0 L). The aqueous layer was back extracted with EtOAc (2 x2.0 L). The combined organic extracts were concentrated on a rotary evaporator to a brown oil. The residue was twice dissolved in EtOAc (1.0 L each time) and concentrated again. The brown oil was then dissolved in MTBE (300 mL) and loaded onto a silica gel column (SiliaFlash G-60, 3.0 L, 1.5 kg) that was pre-conditioned with 10% EtOAc/n-heptane. Thecolumn was then eluted sequentially with 10%, 20% and 30% EtOAc in n-heptane. The fractions were discarded until the eluate was yellow and then collected until cessation of color. Concentration of the combined yellow fractions on a rotary evaporator yields two crops of tert-butyl [5-hydroxy-6-nitro-2-pyridinylj(methyl)carbamate of 61.5 g and 21.3 g, (respective LC purities = 98.7% and 97.0%) with a combined yield of 82.8g (51%).

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; NAVIDEA BIOPHARMACEUTICALS, INC.; CESATI, Richard R., III; CASEBIER, David S.; MORETON, Richard Christian; (49 pag.)WO2017/87965; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 132289-57-7, 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. 132289-57-7, name is N,2-Dimethoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the above amide (260mg) in THF (5ml) at-78 C was added a solution of 2-thienyllithium (1 M in THF, 2. 15ml). The solution was stirred for 2hr at-78 C and warmed to-20 C for an additional 2hr. The reaction was quenched with saturated ammonium chloride and extracted with CH2CI2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 250mg of product (82%).

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

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/68460; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 115643-59-9, These common heterocyclic compound, 115643-59-9, name is 2-Amino-6-fluorobenzamide, 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.

Step 1 To a solution of 2-amino-6-fluorobenzamide (3.80 g, 24.7 mmol) and triethylamine (2.99 g, 29.6 mmol) in THF (50 mL) was added dropwise ethyl chloroglyoxylate (3.70 g, 27.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was suspended in EtOH, and insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate as a white powder (4.95 g, 79%).

Statistics shows that 2-Amino-6-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 115643-59-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 103361-99-5, These common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, 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.

Step A 6-Iodo-7-fluoro-2H-1,4-benzoxazin-3(4H)-one 7-Fluoro-2H-1,4-benzoxazin-3(4H)-one (15.8 g) was mixed with iodine monochloride (15.6 g) in acetic acid (150 ml) and heated to reflux for 36 h. The cooled mixture was treated with saturated aqueous sodium bisulfite until the color was dissipated. The solid was filtered and washed well with water. The solid was air dried and dried further by dissolution in dimethylformamide (100 ml) and evaporated to dryness under reduced pressure to give the desired product (26.3 g) contaminated with some starting material. (The reaction can be taken to completion by addition of more iodine monochloride and refluxing for 24 h longer.) The crude product was used in Step B.

The synthetic route of 103361-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US5670455; (1997); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121492-06-6, 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 121492-06-6 as follows.

General procedure: To a solution of acid 7(a-p) (1 equiv) and amine (1.5 equiv) in dichloromethane were added HoBt (1.5 equiv) and EDCI(1.5 equiv). The reaction mixture was stirred at room temperature overnight, then washed with 5% aqueous HCl, 5% aqueous sodium bicarbonate, water, and brine, and dried. Purification by chromatography afforded 8-9(a-c).

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Ying-Rui; Wei, Jin-Lian; Mo, Xiao-Fei; Yuan, Zhen-Wei; Wang, Jia-Lin; Zhang, Chao; Xie, Yi-Yue; You, Qi-Dong; Sun, Hao-Peng; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2713 – 2718;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 125414-41-7, The chemical industry reduces the impact on the environment during synthesis 125414-41-7, name is tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate, I believe this compound will play a more active role in future production and life.

2.97 g of lipoic acid (LA), 3.31 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC¡¤HCl) was added to a 100 mL round bottom flask.Add 40 mL CH2Cl2 to dissolve and activate for 30 min.1.25 g of Boc-serinol dissolved in 20 mL of CH 2 Cl 2 and 2.21 g of 4-(dimethylamino)pyridine (DMAP) were added to the above mixture.Reaction for 12 h. After the reaction is completed, it is filtered.The filtrate was thoroughly washed with an excess of 0.1 mol/L hydrochloric acid.Discard the water phase after standing. Dry the oil phase with sodium sulfate and purify by column chromatography (eluent: CHCl3/CH3OH=20/1, v/v) to give a pale yellowOily liquid di-Boc-LA-Ser (3.19 g, yield 86%).Take 1g di-Boc-LA-Ser in 10mL CH2Cl2,After cooling to 0 C, 0.41 g of trifluoroacetic acid (TFA) was slowly added dropwise and reacted for 2 h.The mixture was concentrated in vacuo to give a crude di-L-Ser.

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, tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southeast University; Li Xinsong; Ling Longbing; He Wei; (21 pag.)CN109224082; (2019); A;,
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. 3984-14-3, name is N,N-Dimethylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1?-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) ? ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below. 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). were added to a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, and the mixture was placed under N2. After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 C. for 2 h. After cooling to 30 C., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered, and then concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 C., and heptane (2 L) was then added slowly. The resulting mixture was stirred and cooled to 0 C. It was then filtered. The filter cake was rinsed with a small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) ? 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/275930; (2007); 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 20348-09-8 as follows. Safety of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

a) 3,4-Dihydro-2H-pyrido[3,2-&][l,4]oxazine; To an ice-cold solution of 4H-rhoyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TetaF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TetaF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H2O (4 mL) followed by NaOH (4 mL, 15%) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85%) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) delta 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e 31 (M + eta)

According to the analysis of related databases, 20348-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
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. 147962-41-2, name is N-Propylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H10N2O2S

The compound of Example 1 (10 g; 20.6 mmol), propylsulfamide (3.1 g; 22.6 mmol; 1.1 eq.; prepared as described in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861), TBAF.3H20 (19.5 g; 61.7 mmol; 3 eq.) and potassium carbonate (8.5 g; 61.7 mmol; 3 eq.) were suspended in DMSO (100 mL). The mixture was heated to 100C for 1 h and then cooled to 20-25C. Water (100 mL) and DCM (100 mL) were added. The org. layer was washed 3 times with water (100 mL each time), 20% aq. citric acid (100 mL) and water (100 mL) before being concentrated under reduced pressure to dryness. The residue was suspended in EA (15 mL) and heated to reflux. Hept (30 mL) was added. The mixture was allowed to cool to 20-25C on its own. The precipitate was filtered off and rinsed with Hept (10 mL). The beige solid thus collected (11.0 g) was recrystallized from EA (30 mL) and Hept (25 mL) to afford the title compound as a white solid (6.4 g; 53% yield). (0323) The product had MS and NMR data equivalent to those reported in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861. LC-MS (method 1): tR = 1.89 min; 100% a/a.

According to the analysis of related databases, 147962-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; ABELE, Stefan; FUNEL, Jacques-Alexis; SCHINDELHOLZ, Ivan; WO2015/121397; (2015); 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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Amino-4,6-dimethoxybenzamide

A mixture of N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 2.5 mmol), NaHSO3 (0.350 g, 3.3 mmol), and p-TsOH (0.100 g, 0.51 mmol) was added to a solution of 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.5 mmol) in DMA (20 mL). The reaction was stirred at 130 C. for 5 hours and concentrated in vacuo. The residue was diluted with H2O and saturated NaHCO3, then extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded the title compound (0.670 g, 56%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): delta 12.02 (s, 1H), 8.13 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 6.74 (d, J=1.9 Hz, 1H), 6.54 (d, J=2.0 Hz, 1H), 3.85-3.95 (m, 7H), 3.43-3.71 (m, 3H), 2.55-3.00 (m, 3H), 1.97-2.09 (m, 5H), 1.70-1.77 (m, 1H), 1.58-1.61 (m, 1H), 1.25-1.30 (m, 4H), 1.11-1.13 (m, 3H). ESI MS m/z 479 [M+H]+

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics