Tag: M.W=100-200

Application of 16066-84-5, 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. 16066-84-5, name is tert-Butyl methylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00519] Step C: A microwave reaction tube equipped with a stir bar was charged with 6-(((1s,4s)-4-(6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridin-1-yl)cyclohexyl)oxy)-2-methylpyridazin-3(2H)-one (0.029 g, 0.066 mmol), tert-butyl methylcarbamate (0.035 g, 0.26 mmol), dioxane (0.5 mL), dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphane (0.012 g, 0.026 mmol), sodium t-butoxide (0.013 g, 0.13 mmol) and Pd2dba3 (0.012 g, 0.013 mmol) under a nitrogen atmosphere. The tube was sealed and warmed to 100 C overnight, partitioned between water/EtOAc, extracted with EtOAc, dried over sodium sulfate and concentrated. The crude material was taken forward without further purification.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
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Electric Literature of 609-66-5, 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 609-66-5 as follows.

General procedure: An oven-dried Schlenk tube was charged with benzamide 1 (0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and aryl iodide 2 (1.0 mol). The tube was evacuated and backfilled with N2 (3 ×), and then DMEDA (0.2 mmol) and anhyd toluene (5.0 mL) were added. The reaction mixture was stirred at 110 C for 48 h. H2O was added and the crude product was extracted with EtOAc. The combined organic phases were washed with brine and H2O, dried (Na2SO4), and concentrated under reduced pressure. The product was purified by silica gel chromatographyto give the desired N-arylated benzamides (Table 2).

According to the analysis of related databases, 609-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Fei; Wu, San; Hu, Weiye; Zhang, Songlin; Synthesis; vol. 50; 5; (2018); p. 1090 – 1096;,
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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. 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4424-80-0

To a mixture of 4,5-dihydro-lH-benzo[b]azepin-2(3H)-one (10.6 g, 65.8 mmol) in DCM (150 mL) cooled in an ice/water bath was added TMEDA (29.8 mL, 197 mmol), then dropwise over 20 minutes was added TMSI (26.9 mL, 197 mmol). The mixture was stirred cooled for 60 minutes, iodine (25.03 g, 99 mmol) was added and the mixture was stirred cooled for another 60 minutes. The reaction was quenched with 5% Na2S2C”3 and stirred 15 minutes. The resulting solid was filtered and dried to give 11.3 g tan solid. Layers of filtrate were separated. Organics were concentrated to a solid, triturated in diethyl ether and solid was filtered and dried to give 5.52 g light brown solid (87% yield, both batches). 1H MR (DMSO-de) delta: 9.93 (s, 1H), 7.22 – 7.30 (m, 2H), 7.09 – 7.17 (m, 1H), 6.99 (d, J = 7.3 Hz, 1H), 4.63 (dd, J = 9.1, 6.8 Hz, 1H), 2.52 – 2.81 (m, 4H); MS (m/z) 288.0 (M+H+).

The synthetic route of 4424-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); A1;,
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Reference of 326-67-0,Some common heterocyclic compound, 326-67-0, name is N-(2-Fluoro-4-methylphenyl)acetamide, molecular formula is C9H10FNO, 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 546 g (3.27 mol) of crude 2-fluoro-4-methyl-acetanilide was added chlorosul- phonic acid (2000 g, 17.24 mol) with stirring at a temperature below 70C. Stirring was continued for 3 hours at a temperature of 70C. The reaction mixture was poured onto ice and then extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to yield the title compound (500 g, 57.8%). H NMR (400 MHz, CDCI3): delta = 9.1 (d, 1 H, J = 7.2 Hz), 7.39-7.52 (m, 1 H), 7.14 (d, 1 H, J = 1 1 .2 Hz), 2.72-2.78 (m, 3H), 2.2-2.3 (m, 3H).

The synthetic route of 326-67-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KAISER, Florian; GROss, Steffen; LANGEWALD, Juergen; NARINE, Arun; WO2013/30262; (2013); A1;,
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Synthetic Route of 125414-41-7, 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. 125414-41-7, name is tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

tert-Butyl (l,3-dihydroxypropan-2-yl)carbamate (3.7 g, 19.35 mmol), potassium hydroxide (4.0 g, 71.59 mmol), and benzyl bromide (12.24 g, 71.59 mmol) were dissolved in 50 mL of DMF. The mixture was stirred for 2 h and concentrated under vacuum. The crude product was purified using column chromatography to yield tert-butyl (1 ,3-bis(benzyloxy)propan-2- yl)carbamate (3.25 g, 45% yield).

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; NEKTAR THERAPEUTICS (INDIA) PVT.LTD.; NEKTAR THERAPEUTICS (Incorporated under the Laws of Delaware and domiclled in the State of California); DUARTE, FRANCO; ANAND, NEEL; SHARMA, PANKAJ; SINGH, DEVENDRAPRATAP U.; WO2015/79459; (2015); A1;,
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Some common heterocyclic compound, 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, molecular formula is C7H7N3O2S, 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. Computed Properties of C7H7N3O2S

Example 1 (E)-1-(benzotriazol-1-yl)-3-phenyl-2-propen-1-one 1.42 g (0.01 mol) of trans-cinnamic acid (compound of formula IV) and 1.97 g (0.01 mol) of 1-(methylsulfonyl)benzotriazole are stirred at room temperature in 50 ml of tetrahydrofuran, followed by dropwise addition of 0.014 mol of triethylamine. The solution is then refluxed for 24 hours, and then evaporated under reduced pressure. The residue is taken up in 60 ml of water and extracted with 70 ml of ethyl acetate. The organic phase is dried, filtered and then concentrated under vacuum. The powder obtained is taken up in 50 ml of acetonitrile and filtered off by suction. 2.24 g of a white powder are obtained. Melting point: 157 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37073-15-7, its application will become more common.

Reference:
Patent; PRODUITS CHIMIQUES AUXILIAIRES ET DE SYNTHESE; Rault, Sylvain; Lancelot, Jean Charles; Suzanne, Peggy; Voisin-Chiret, Anne-Sophie; Pecquet, Regis; Joseph, Jean-Christophe; US2013/165507; (2013); A1;,
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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 16066-84-5 as follows. Recommanded Product: 16066-84-5

To a solution of tert-butyl-N-methylcarbamate (3.00 g, 22.9 mmol) in THF (50 mL) was added NaH (1 .37 g, 34.3 mmol) in portions at 0 C. The reaction mixture was stirred at 15 C for an hour. Then 81 (5.24 g, 22.9 mmol) in THF (20 mL) was added dropwise. The reaction mixture was stirred at 15 C for 13 h. The reaction was quenched by ice water (10 mL) slowly and then extracted with EtOAc (20 mL x 3). The combined organic phase was washed with brine (10 mL x 2), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified via silica gel columnchromatography (petroleum ether/ethyl acetate = 4:1) to give 82 (2.9 g, 45%) as a colorless oil.1H N R (400 MHz, CDCI3) 7.95-7.91 (m, 2H), 7.42-7.38 (m, 2H), 4.45 (s, 2H), 3.91 (s, 3H), 2.85 (s, 3H), 1 .48 (s, 9H). To a solution of 82 (2.8 g , 10 mmol) in THF (20 mL) was added LiAIH4(456 mg , 12.0 mmol) in portions at 0 C. The mixture was stirred at 15 C for 2 hours. The mixture was cooled to 0 C and quenched by saturated solution of potassium sodium tartrate (0.5 mL), the mixture was concentrated in vacuum (40C) to give 83 (1 .8 g, 71 %) as a colorless oil.1H NMR (400 MHz, CDCI3) 7.32-7.29 (m, 2H), 7.27-7.23 (m, 1 H), 7.15-7.14 (m, 1 H), 4.68 (s, 2H), 4.42 (s, 2H), 2.82 (s, 3H), 1 .48 (s, 9H). To a solution of 83 (1 .5 g, 6.0 mmol) in DCM (20 mL) was added A/-Fmoc-(S)-valine (2.23 g, 6.57 mmol), DCC (1 .6 g, 7.8 mmol) and DMAP (73 mg, 0.60 mmol). The mixture was stirred at 15 C for 12 h. Then DCM (10 mL) was added and the organic layer was washed with brine (10 mL x 3), dried over Na2S04and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate = 4: 1) to give 84 (1 .8 g, 53%) as a colorless oil.1H NMR (400 MHz, CDCI3) 7.70-7.80 (m, 2H), 7.54-7.62 (m, 2H), 7.35-7.42 (m, 2H), 7.23-7.33 (m, 4H), 7.19 (br s, 2H), 5.34-5.32 (m, 1 H), 5.29-5.14 (m, 2H), 4.43-4.41 (m, 4H), 4.40-4.14 (m, 4H), 2.83 (s, 3H), 2.12-2.23 (m, 1 H), 1 .47 (s, 9H), 0.86 (dd, J – 6.84, 2.87 Hz, 6H). To a solution of 84 (1 .00 g, 1 .75 mmol) in THF (6 mL) was added piperidine (298 mg, 3.50 mmol). The mixture was stirred at 15 C for 12 h . The mixture was concentrated in reduced pressure at 40 C. The residue was purified by column chromatography (petroleum ether/ethyl acetate = 1 :4) to give 85 (400 mg, 65%) as a colorless oil.1H NMR (400 MHz, DMSO-d6) 7.37-7.35 (m, 1 H), 7.34-7.29 (m, 1 H), 7.27-7.22 (m, 1 H), 7.18-7.17 (m, 1 H), 5.16-5.06 (m, 2H), 4.37 (s, 2H), 3.15 (d, J – 4.0 Hz, 1 H), 2.74 (s, 3H), 1 .99-1 .84 (m, 1 H), 1 .42-1 .39 (m, 9H), 0.85 (d , J = 6.8 Hz, 3H), 0.79 (s, J = 6.4 Hz, 3H). To a solution of Acid-04 (164 mg, 0.856 mmol) in DMF (3 mL) was added HATU (390 mg, 1 .03 mmol) and TEA (260 mg, 2.57 mmol). The mixture was stirred at 20 C for 1 h. Then 85 (300 mg, 0.856 mmol) was added in one portion. The mixture was stirred at 20 C for 1 1 h. The reaction was quenched by water (10 mL) slowly at 0 C and then extracted with EtOAc (10 mL x 3). The combined organic phase was washed with brine (10 mL x 1), dried over anhydrous Na2S04, filtered and then HCI/EtOAc (4 M, 4 mL) was added. The mixture was stirred at 20 C for 12 h. The mixture was concentrated in vacuo. The residue was purified by prep. HPLC (column: Luna C18 100 x 30 mm; liquid phase: 0.1 %TFA-ACN; B%: 10%-40%, 12 min). After prep. HPLC, 3N HCI (2 mL) was added before freeze drying. 6-122 (137 mg, 33%) was obtained as an off white solid.1H N R (400 MHz, DMSO-cfe) 9.21 (br s, 2H), 9.03 (s, 1 H), 8.59 (d, J – 8.0 Hz, 1 H), 7.55-7.51 (m, 2H), 7.46-7.45 (m, 2H), 7.35 (d, J – 8.0 Hz, 1 H), 7.24 (d, J – 8.0 Hz, 1 H), 5.19 (s, 2H), 4.97 (s, 2H), 4.37 (t, J – 8.0 Hz 1 H), 4.10 (s, 2H), 2.39 (s, 3H), 2.21 -2.16 (m, 1 H), 0.96 (d, J = 6.0 Hz, 6H); ESI-MS m/z 425 [M+H]+; HPLC purity: 94.93% (220 nm), 87.86% (254 nm).

According to the analysis of related databases, 16066-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); 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. 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

To a 500 ml three-mouth bottle by adding 200 ml of THF, cooling to 5 C the following add 17.3g (0.46mol, 4 . 0eq) of lithium aluminum hydride, then lower the temperature to the -5 C the following, the three aluminum chloride 3.0g (0.023mol, 0 . 2eq) THF slowly dropwise to the reaction in the solution, stirring for 10 min, temperature at 5 C the following starting to drop plus step amide 19.0g (0.114mol, 1 . 0eq) in 100 ml of solution THF. Added after stirring overnight TLC inspection reaction end, cooling to 0 C the following, starting the dropping water filtration, the filter cake is washed with dichloromethane eluviation, concentrated filtrate, vacuum distillation, to obtain colorless oily liquid 12.0g product. Yield: 71.0%, GC: 99.9%

The synthetic route of 6331-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shao Yuan Science and Technology (Shanghai) Co., Ltd.; Wu, Yong; Lei, Ting jun; Qi, Ming; (12 pag.)CN105461659; (2016); A;,
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Synthetic Route of 116861-31-5, These common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)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.

To a solution of 5-3 (40 mg, 97 pmol) and 19-1-1A (23 mg, 116 pmol) in DMF (300 uL) was added K2CO3 (27 mg, 194 pmol). The mixture was mixture was stirred at room temperature for 16 hr. The reaction cooled and diluted with DCM (5 mL). The solution was filtered and the filtrate was concentrated under reduced pressure. The crude was purified by flash column chromatography (ISCO, silica, l2g, ethyl acetate in hexanes) to afford 15 (18.9 mg, 34% yield).

Statistics shows that tert-Butyl (3-chloropropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 116861-31-5.

Reference:
Patent; TP THERAPEUTICS, INC.; ROGERS, Evan W.; CUI, Jingrong Jean; ZHAI, Dayong; ZHANG, Han; UNG, Jane; DENG, Wei; WHITTEN, Jeffrey; (146 pag.)WO2019/126121; (2019); A1;,
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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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H18N2O2

A mixture of (R)-4-(6-fluoropyridin-3 -yl)-6-(2-hydroxypropoxy)pyrazolo[ 1,5 – a]pyridine-3-carbonitrile (Intermediate P66; 100 mg, 0.320 mmol) 3,6-diaza- bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (95.2 mg, 0.480 mmol) and K2C03(s) (443 mg, 3.20 mmol) in DMSO (1601 tL) was stirred for 3 d at 80 °C. The reaction mixture was cooled to ambient temperature, then diluted with water (10 mL), and extracted with DCM (4 x 10 mL). The combined organic extracts were washed with brine (10 mL), then dried over anhydrous Na2SO4(), filtered, and concentrated in vacuo. The crude residue was purified by silica chromatography (using 50-100percent EtOAc in Hexanes as the gradient eluent) to cleanly provide the title compound (97 mg, 62percent yield). MS (apci) m/z = 491.2 (M+H).

According to the analysis of related databases, 869494-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
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