Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, belongs to ethers-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 658-89-9, Computed Properties of C7H7F3N2O

2-Methyl-5-trifluoromethoxybenzimidazole. The starting material, 2-amino-4-trifluoromethoxyaniline, was obtained by the method of Yagupolskii, L. M. et al. (Yagupolskii L. M., Troitskaya V. I. J. Gen. Chem. USSR Engl. Transl., 1961, Vol. 31, p. 845; Chem. Abstr. 1961, Vol. 55, p. 22830f). The procedure of Philips, M. A. (Philips M. A. J. Chem. Soc. 1929, p. 2820-2828) was used to produce 2-methyl-5-trifluoromethoxybenzimidazole. To 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) acetic acid anhydride (1.5g, 0.0146 Mol) was carefully added at 20 C. and the mixture was stirred 5 minutes at this temperature. Then 2-3 drops of concentrated aqueous HCl was added with stiffing, and the mixture was refluxed for 7 hours The reaction solution was cooled and diluted with water (10 mL), 0.5 g of charcoal was added, and the mixture was refluxed more 5-10 min. After cooling, the mixture was filtered and resulted clear filtrate was washed with ether (2×10 mL). The water layer was neutralized with excess of dilute NH4OH -(charcoal was filtered) The precipitate was filtered, washed with water and dried to give a solid (0.34 g, 44% by wt. pure). M.p. 135-137 C. 1H NMR (DMSO-d6): 2.49 (s, 3H), 7.17 (d, J=8.5 Hz, 1H), 7.34 (s, 1H), 7.62 (d, J=8.5 Hz, 1H). 13C NMR (DMSO-d6): 14.47, 107.44, 114.19, 117.25, 120.28 (q, J=255.2 Hz), 137.06, 139.46, 143.09, 153.26. 19F NMR (DMSO-d6): -57.41. [M+1]+ 217.

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-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The United States of America as represented by the United States Department of Energy; US8242284; (2012); B1;,
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Reference of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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 14 N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0292) To a mixture of 3-fluoro-4-(trifluoromethoxy)aniline (66 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (63 mg). 1H NMR (300 MHz, CDCl3) delta3.98 (2H, s), 6.82 (1H, d, J = 6.8 Hz), 7.08-7.24 (3H, m), 7.52 (1H, s), 7.58 (1H, d, J = 9.0 Hz), 7.61-7.74 (2H, m), 8.12 (1H, brs)

The synthetic route of 1017779-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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Electric Literature of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 26; 5-Chloro-thiophene-2-carboxylic acid (2,2-diethoxyethyl) amide; Add 5-chlorothiophene-2-carboxylic acid (100 g, 0.60 mol) and dichloromethane (1000 mL) to a 3 L three-necked round bottom flask equipped with an overhead stirrer, nitrogen inlet/outlet, addition funnel, and thermocouple. Stir the resulting solution under nitrogen while cooling to 4 0C. Add via addition funnel 2,2-diethyoxyethylamine (88.5 ml, 0.60 mol) in dichloromethane (35 mL) over 12 minutes. Add l-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (123 g, 0.64 mol) to the chilled mixture. Add additional dichloromethane (165 mL) and stir the reaction mixture for 22 h at room temperature. Quench the reaction with water (1000 mL) and separate the resulting layers. Back extract the aqueous layer with dichloromethane (500 mL) and combine the organic layers. Dry over sodium sulfate and purify through a silica gel bed eluting with dichloromethane followed by a mixture of 1% MeOH in dichloromethane and then a mixture of 10% MeOH in dichloromethane to afford 108 g (65%) of the title compound as a white solid. 1H NMR (500 MHz, CDCl3): delta 7.26 (d, J= 3.5 Hz, IH), 6.85 (d, J= 3.5 Hz, IH), 6.37 (bs, IH), 4.57 (t, J= 5.5 Hz, IH), 3.68-3.74 (m, 2H), 3.48-3.57 (m, 4H), 1.19 (t, J= 7.5 Hz, 6H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, belongs to ethers-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 54149-17-6, Recommanded Product: 54149-17-6

A mixture of 5-nitro-1,2-dihydro-indazol-3-one (399 mg, 2.22 mmol), 1-bromo-2-(2-methoxy-ethoxy)-ethane (454 uL, 3.34 mmol), potassium iodide (370 mg, 2.22 mmol) and 1N sodium hydroxide solution (6.7 mL, 6.7 mmol) in 2 ml dioxane was stirred at 60 C. overnight. The reaction mixture was then cooled, poured into 50 mL H2O and 300 muL 10N NaOH was added. The aqueous layer was extracted with CH2Cl2 and then acidified to pH 2 with 6N HCl. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography to afford the product 1-[2-(2-methoxy-ethoxy)-ethyl]-5-nitro-1,2-dihydro-indazol-3-one (380 mg, 61%). ES-MS calcd for C12H15N3O5 (m/e) 281.26, obsd 282.17 (M+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, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bolin, David Robert; Cai, Jianping; Cheung, Adrian Wai-Hing; Goodnow, JR., Robert Alan; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Yun, Weiya; US2009/76275; (2009); A1;,
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Related Products of 15799-79-8, 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. 15799-79-8 name is 3-Methoxy-N,N-dimethylaniline, 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.

[0147] (S)-3-(4-Dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol: To a 50-mL roundbottom flask equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (0.394 g, 1.60 mmol, 0.100 equiv), CH2Cl2 (16.0 mL), HCl (as a 4N solution in 1,4-dioxane, 0.400 mL, 1.60 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (4.69 mL, 32.0 mmol, 2.00 equiv). The reaction vessel was cooled to 0o C. before the addition of cinnamaldehyde (2.06 ml, 16.0 mmol, 1.00 equiv). The solution was stirred for 12 h at 0o C. and then warmed to ambient temperature and stirred for an additional 6 h. At that time, the reaction mixture was added drop-wise to a stirring suspension of NaBH4 (0.750 g, 0.198 mmol, 1.24 equiv) in ethanol. After 5 min, the reduction was quenched with saturated aqueous NaHCO3 solution and diluted with CH2Cl2. The layers were separated and the organic was washed with saturated aqueous NaHCO3 and brine solutions. The resulting solution was dried over sodium sulfate and concentrated in vacuo to give a pale yellow residue, which was purified by silica gel chromatography. Gradient elution with 25-50% EtOAc in hexanes afforded the product as a colorless oil in 81% yield (3.70 g, 13.0 mmol); 74% ee. 1H NMR (300 MHz, CDCl3) ?7.32-7.12 (m, 5H, ArH), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.7, 8.8 Hz, 1H, ArH), 6.27 (d, J=2.2, Hz, 1H, ArH), 4.51 (dd, J=6.6, 8.8 Hz, 1H, ArCH), 3.83 (s, 3H, OCH3), 3.65-3.48 (m, 2H, CH2OH), 2.93 (s, 6H, N(CH3)2), 2.38-2.12 (m, 2H, CHCH2), 1.98 (br s, 1H, OH); 13C NMR (75 MHz, CDCl3) ?157.8, 150.5, 145.5, 128.8, 128.4, 128.2, 125.9, 121.3, 105.5, 96.6, 61.6, 55.9, 41.1, 38.7, 38.2. [0148] The enantiomeric ratio of the product was determined by HPLC analysis using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=12.9 min, S isomer tr=18.1 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-N,N-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. Recommanded Product: 2-(2-Chloroethoxy)acetic acid

In a three-necked round-bottom flask under nitrogen atmosphere equipped with a mechanical stirrer, a thermometer, a condenser and a dropping funnel 6.87 g (0.05 mol) phosphorus trichloride and 10.75 g (0.05 mol) Amberlyst-15 (hydrogen form, dry) were mixed with 50 ml chlorobenzene . Slowly 6.90 g of (0.05 mol) 5-chloro-3- oxapentanoic acid was added drop-wise. After completed addition the reaction mixture was heated to 50 °C for 4 h. During the addition and reaction time the evolution of CO was observed. Then 10 ml water was added and the Amberlyst- 15 was filtered off. The solution was analyzed by ChiEta- and 31P-NMR spectroscopy and 4-Chloro-2-oxabutanyl-l-phosphonic acid observed at 58.9 percentw/w.

The synthetic route of 2-(2-Chloroethoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STRAITMARK HOLDING AG; BURCK, Sebastian, R., W.; NOTTE, Patrick; WO2013/17564; (2013); A2;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H8F3NO

General procedure: 5.3g (0.02 mol) of methyl N-nitro-1,3-dioxoisoindoline-2-carbimidothioate (3) was dissolved in 120 mL of acetonitrile, and cooled to 0-5, dropped in a quantity of 0.02 mmol of (aryl)methanamine over 5 mins. The reaction was stirred at 0-5 for one hour again. The mixture was filtered, concentrated in vacuo and recrystallised in EtOAc – petroleum ether (1:1) to give pure products 4a~4f.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Qinglai; Zhao, Fenghai; Zhu, Xiang; Zhou, Ziyuan; Yang, Dongyan; Xu, Zhihong; Li, Junkai; Qin, Zhaohai; Natural Product Research; (2019);,
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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. 134364-69-5, name is 2,3-Difluoroanisole, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Example 1; 2′-Chloro-2,5-difluoro-4-methoxybenzophenone Aluminum chloride (92.54 g, 694 mmol) was transferred to a bottle (in a glove bag under dry N2), then to the reaction flask. Dichloromethane (600 mL) was added via syringe and the suspension cooled to 0 C. (ice-H2O bath). 2-Chlorobenzoyl chloride (88.2 mL, 121.45 g, 694 mmol) was added via syringe at 0-5 C. over 13 min. The addition funnel was rinsed with 10 mL dichloromethane. The difluoroanisole (77.8 mL, 100.0 g, 694 mmol) was then added dropwise via syringe at 0-5 C. over 13 min. The resulting yellow solution was stirred at 0-5 C. for 3.5 h (until the bath warmed) then at 20-25 C. for 14 h.The solution is poured over 600 g ice in a 2 L round bottom flask. Dichloromethane (80 mL) was used to complete the transfer. The layers were separated and the aqueous layer was extracted with 80 mL dichloromethane. The combined organic layers were transferred to a 1 L flask (with paddle stirrer) for distillation under dry N2. The dichloromethane is then replaced by n-heptane. At a bath temperature of 55-65 C., the head temperature is 35-38 C. and the pot temperature climbs to as high as 52 C. The pot solution is cooled and n-heptane (400 mL) is added. The distillation is continued. At a bath temperature of 100 C., the head temperature climbs from 55 to 75 C. and pot temperature climbs to as high as 83 C. before stopping the distillation (collected 767 mL total distillate). The pot suspension is now two phases, colorless on top and yellow on bottom. The suspension is allowed to cool to 50 C. and stirred at 200 rpm for 1 h. The suspension is allowed to cool to 40 C. and stirred at 200 rpm for 1 h. The suspension is allowed to cool to 30 C. and stirred at 200 rpm for 1 h. The 30 C. suspension is then cooled to 0-5 C. and stirred for 30 min. The precipitate is suction filtered (600 ml coarse sintered glass funnel), washed with 100 mL n-heptane at 0 C., and air dried 17 h at 25 C. to afford 181.23 g (92.4%) of light yellow solid.Recrystallization from hexanes provides colorless crystals, m.p. 84-85 C.; 500 MHz 1H NMR (CDCl3) delta 7.56 (dd, J=6.5 Hz, J=11.5 Hz, 1H), 7.43-7.39 (m, 3H), 7.38-7.34 (m, 1H), 6.65 (dd, J=6.6 Hz, J=11.5 Hz, 1H), 3.94 (s, 3H); 125 MHz 13C NMR (CDCl3) delta 190.2, 159.2 (dd, J=2 Hz, J=253 Hz), 153.9, 148.7 (dd, J=3 Hz, J=244 Hz), 140.0, 131.7, 131.21, 131.19, 130.2, 129.08, 129.07, 127.1, 117.5 (dd, J=3 Hz, J=21 Hz), 101.7 (dd, J=2 Hz, 29 Hz), 56.9; IR (KBr) 3057, 2986, 2941, 1663, 1653, 1620, 1519, 1443, 1420, 1360 cm-1. Elem. Anal. Calcd for C14H9ClF2O2: C, 59.49; H, 3.21; Cl, 12.54; F, 13.44. Found: C, 59.49; H, 3.13.

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; Roche Colorado Corporation; US2009/203901; (2009); A1;,
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Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl (2S)-5-amino-6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-1-carboxylate (300 mg, 1.00mmol, Intermediate 1) was dissolved in toluene (5 mL). Then 3,3- diethoxypropan-1-amine (885 mg, 6.01mmol), 3rd Generation BrettPhos precatalyst (91 mg, 0.10mmol), BrettPhos (108 mg, 0.20mmol) and sodium tert-butoxide (289 mg, 3.01mmol) were added successively. The resulting solution was stirred for 2 h at 110oC under nitrogen atmosphere. The reaction mixture was cooled and the resulting solids were filtered out. The filtrate was concentrated under vacuum. The residue was subjected to purification by FCC eluting with ethyl acetate/petroleum ether (2:1). This afforded the title compound (240 mg, 62%) as a yellow oil. MS: (ES, m/z): 366 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; SCHILLER, Shawn E.R.; HERBERTZ, Torsten; LI, Hongbin; GRAVES, Bradford; MISCHKE, Steven; WEST, Angela V.; ERICSSON, Anna; DOWNING, Jennifer R.; (484 pag.)WO2019/55877; (2019); A1;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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: C6H15NO2

2,2-Diethoxyethylamine (470 muL, 3.23 mmol) was added to a suspension of pyrimidine 9 (0.63 g, 2.67 mmol) in i-PrOH (30 mL), and the mixture was stirred at r.t. until the starting compound has dissolved. Et3N (560 muL, 4.0 mmol) was then added and the mixture was stirred for a further 45 min. H2O (50 mL) was added and the product was extracted with CH2Cl2 (2 × 50 mL). The organic layers were combined, washed with H2O (2 × 20 mL), dried (Na2SO4), and concentrated. The residue was purified by flash chromatography(silica gel, CH2Cl2; Rf = 0.42) to give a yellow solid; yield: 0.61 g(69%); mp 65.5-67.5 C.IR (KBr): 3380 (NH) cm-1. 1H NMR (300 MHz, CDCl3): delta = 1.27 (t, J = 6.9 Hz, 6 H, 2 × CH3),2.55 (s, 3 H, SCH3), 3.60 (dq, 2J = 9.3 Hz, 3J = 6.9 Hz, 2 H,2 × CHAHBCH3), 3.72-3.83 (m, 4 H, NCH2 and 2 × CHAHBCH3),4.09 (s, 3 H, OCH3), 4.68 (t, J = 5.4 Hz, 1 H, OCH), 8.84 (br s, 1 H,NH).13C NMR (75 MHz, CDCl3): delta = 14.8, 15.6, 44.3, 55.7, 63.2, 100.5,113.5, 156.6, 163.8, 174.6.Anal. Calcd for C12H20N4O5S: C, 43.36; H, 6.07. Found: C, 43.68;H, 6.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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