Tag: M.W=100-200

These common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, 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. Quality Control of 2-Phenoxyaniline

A 100mL round bottom flask was charged with 1H-pyrrole-2-carboxaldehyde (1.862g, 20mmol), 2-Phenoxybenzenamine (3.704g, 20mmol) and 30mL methanol. After adding formic acid (0.01equiv, 0.2mmol), the mixture was stirred for 24h. The solution was evaporated to dryness, and recrystallized from CH2Cl2/n-hexane. Pure L1 was obtained as white powder. Yield: 4.82g, 92%. 1H NMR spectrum (400MHz, CDCl3, ppm), delta: 6.25(dd,1H), 6.62(dd,1H), 6.69(s,1H), 6.94(s,1H), 6.96(s,1H), 7.02(t,2H), 7.15(m,3H), 7.28(m,2H), 8.25 (s,1H), 9.32(s,1H). 13C NMR spectrum (100MHz, CDCl3,ppm), delta: 110.31, 116.50, 117.77, 120.9, 121.08, 122.45, 123.13, 124.75, 126.18, 129.52, 130.39, 143.95, 149.08, 150.72, 158.18. HRMS (m/z): [M+ H]+ calcd for 263.11789, found 263.11777.

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

Reference:
Article; Zhang, Dan; Pang, Wenmin; Chen, Changle; Journal of Organometallic Chemistry; vol. 836-837; (2017); p. 56 – 61;,
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Electric Literature of 910251-11-5, 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. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, This compound has unique chemical properties. The synthetic route is as follows.

Potassium methoxymethyltrifluoroborate (18 mg, 0.12 mmol), l-(6- bromospiro[chroman-2, 1 ‘-cyclobutan] -4-yl)-3 -( 1 ‘,4-dimethyl- 1 -phenyl- 1 H, 1 -[3 ,4′-bipyrazol] – 5-yl)urea (Example 34; 33 mg, 0.060 mmol), dichloro[l,l’-bis(diphenylphosphino)- ferrocene]palladium (II) dichloromethane adduct (9.8 mg, 0.012 mmol) and Cs2C03 (98 mg, 0.30 mmol) were combined in dioxane (2 mL) and water (0.5 mL) and degassed by bubbling N2 through the mixture for 10 minutes, The reaction was then sealed in a glass tube and heated at 100 C for 3 hours. The reaction was cooled, poured into brine (10 mL) and extracted with EtOAc (2 x 10 mL). The combined organic extracts were concentrated and purified by reverse- phase column chromatography using 0-70% acetonitrile/H20 as the eluent to provide the title compounds: l-(l’,4-dimethyl-l-phenyl-lH,rH-[3,4′-bipyrazol]-5-yl)-3-(6- (methoxymethyl)spiro[chroman-2, -cyclobutan]-4-yl)urea [second peak, 2.8 mg, 0.0055 mmol, 9.1% yield, MS (apci) m/z = 513.3 (M+H)] and l-(l’,4-dimethyl-l-phenyl-lH,l’H-[3,4′- bipyrazol]-5-yl)-3-(spiro[chroman-2, -cyclobutan]-4-yl)urea [first peak, 2.50 mg, 0.0053 mmol, 8.8% yield, MS (apci) m/z = 469.2 (M+H)].

The chemical industry reduces the impact on the environment during synthesis Potassium trifluoro(methoxymethyl)borate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven, Wade; BLAKE, James, F.; BRANDHUBER, Barbara, J.; HAAS, Julia; JIANG, Yutong; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; THOMAS, Allen, A.; WINSKI, Shannon, L.; WO2014/78454; (2014); A1;,
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Application of 38336-04-8, These common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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.

Compound 12 was synthesized by the method described in Synth. Commun.,25, 907 (1995), and Compound 13 and Compound 2 were synthesized by the method described in J. Ned. Chem., 38, 1673 (1995). Succinic anhydride (150.1 mg, 1.5 mmol) was gradually added to a pyridine solution (2.0 ml) of each of Compounds 12, 13 and 2 (1.0 mmol) at room temperature, followed by stirring at 100C for 1.5 to 4 hours, respectively. The reaction solution was cooled to room temperature, and 2 mol/l hydrochloric acid was added thereto, followed by extraction with dichloromethane. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:3) to give each of Compounds 14 to 16, respectively (yield 92 to 100%). (Compound 14)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.51 (2H, t, J=7.0Hz), 2.69 (2H, t, J=7.0Hz), 3.49 (2H, t, J=5.0Hz), 3.59 (2H, t, J=5.0Hz), 4.54 (2H, s), 6.20 (1H, t, J=5.0Hz), 7.31-7.42 (5H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 175.8 (C), 172.5 (C), 137.4 (C), 128.1 (CHx2), 127.5 (CH×2), 127.5 (CH), 72.6 (CH2), 68.2 (CH2), 39.1 (CH2), 30.2 (CH2), 29.2 (CH2). (Compound 15)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.49 (2H, t, J=5.0Hz), 2.57 (2H, t, J=5.0Hz), 3.54 (2H, dd, J=7.2, 4.9Hz), 3.64 (2H, dd, J=7.2, 3.0Hz), 4.25-4.32 (1H, m), 4.50 (4H, s), 6.09 (1H, d, J=6.9Hz), 7.25-7.37 (10H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 175.8 (C), 171.6 (C), 137.7 (C×2), 128.3 (CHx4), 127.6 (CH×4), 127.6 (CH×2), 127.6 (C), 73.1 (CH2×2), 68.3 (CH2×2), 48.7 (CH), 30.6 (CH2), 29.6 (CH2). (Compound 16)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.06 (2H, t, J=5.0Hz), 2.44 (2H, t, J=5.0Hz), 3.50-3.82 (14H, m), 4.09-4.16 (1H, m), 4.50 (2H, s), 4.50 (2H, s), 6.82 (1H, d, J=6.5Hz), 7.25-7.36 (20H, m).13C-NMR (CDCl3, 300MHz) delta (ppm): 175.3 (C), 172.0 (C), 137.9 (C×2), 137.7 (C×2), 128.2 (CH×4), 128.2 (CH×4), 127.7 (CH×4), 127.6 (CH×4), 127.5 (CH×2), 127.4 (CH×2), 78.9 (CH×2), 73.4 (CH2×2), 73.2 (CH2×2), 70.5 (CH2×2), 69.9 (CH2×2), 68.4 (CH2×2), 49.6 (CH), 30.1 (CH2), 30.0 (CH2). NHS (126.6 mg, 1.1 mmol), EDC (412.7 mg, 2.0 mmol) and triethylamine (0.11 ml, 0.8 mmol) were added to a tetrahydrofuran solution (45 ml) of each of Compounds 14 to 16 (1.0 mmol) in this order at room temperature, followed by refluxing for 2 to 4 hours. Then, 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:10) to give Compounds 17 to 19, respectively (yield 53 to 90%). (Compound 17)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.61 (2H, t, J=7.0Hz), 2.87 (4H, s), 3.19 (2H, t, J=7.0Hz), 3.49 (2H, t, J=5.0Hz), 3.59 (2H, t, J=5.0Hz), 4.55 (2H, s), 6.13-6.25 (1H, m), 7.31-7.42 (5H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 170.1 (C×2), 169.1 (C), 168.2 (C), 137.8 (C), 128.5 (CH×2), 127.9 (CH××2), 127.9 (CH), 73.2 (CH2), 68.9 (CH2), 39.5 (CH2), 30.6 (CH2), 26.8 (CH2), 25.5 (CH2×2). (Compound 18)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.59 (2H, t, J=5.5Hz), 2.79 (4H, s), 2.98 (2H, t, J=5.5Hz), 3.54 (2H, dd, J=7.5, 5.0Hz), 3.64 (2H, dd, J=7.5, 3.0Hz), 4.27-4.34 (1H, m), 4.51 (4H, s), 5.95 (1H, d, J=6.8Hz), 7.25-7.39 (10H, m). 13C-NMR (CDCl3, 75MHz) delta (ppm): 169.3 (C), 168.7 (C×2), 167.9 (C), 137.9 (C×2), 128.2 (CH×4), 127.6 (CHx4), 127.5 (CH×2), 73.1 (CH2×2), 68.3 (CH2×2), 48.6 (CH), 30.7 (CH2), 26.7 (CH2), 25.5 (CH2×2). (Compound 19)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.12 (2H, t, J=5.8Hz), 2.77-2.82 (6H, m), 3.51-3.82 (14H, m), 4.09-4.17 (1H, m), 4.50 (2H, s), 4.51 (2H, s), 6.68 (1H, d, J=7.0Hz), 7.27-7.35 (20H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 169.2 (C), 68.7 (C×2), 167.8 (C), 138.0 (C×2), 137.8 (C×2), 128.3 (CH×4), 128.2 (CH×4), 127.7 (CH×4), 127.6 (CH×4), 127.4 (CH×4), 79.0 (CH×2), 73.4 (CH2×2), 73.3 (CH2×2), 70.6 (CH2×2), 70.0 (CH2×2), 68.5 (CH2×2), 49.4 (CH), 29.8 (CH2), 26.5 (CH2), 25.0 (CH2×2). N-(8-aminooctyl)benzamide hydrochloride (compound Ra-H·HCl) was synthesized by the method described in Synthesis, 917 (1988). Compound Ra-H·HCl (284.8 mg, 1.0 mmol) and triethylamine (0.14 ml, 1.0 mmol) were added to a tetrahydrofuran solution (20 ml) of each of Compounds 17 to 19 and 6 (1.0 mmol) in this order at room temperature, followed by stirring at the same temperature for 3 to 6 hours. Then, 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate and then filtered. The solvent…

Statistics shows that 2-(Benzyloxy)-1-ethanamine is playing an increasingly important role. we look forward to future research findings about 38336-04-8.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; Tecno Network Shikoku Co.,Ltd.; EP1550651; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, 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 651734-54-2, Quality Control of 2,6-Difluoro-3,5-dimethoxyaniline

A mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.50 g, 5.19 mmol), 2,6-difluoro-3,5-dimethoxyaniline (1.08 g, 5.71 mmol) in N,N-diisopropylethylamine (4 mL) was stirred at 80 C. for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0-40% EtOAc in DCM) to give 1.70 g desired product. LCMS calculated for C1-3H12Cl2F2N3O2[M+H]+ m/z: 350.0. Found: 350.0.

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, 2,6-Difluoro-3,5-dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Lu, Liang; Qian, Ding-Quan; Shen, Bo; Yao, Wenqing; (40 pag.)US2016/115164; (2016); A1;,
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Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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: 36865-41-5

76.4 m76.4 mmol), l-bromo-3-methoxy-propane ( 12.9 g, 84 mmol ), K2CO3 (22 g, 21 53 mmol) and DMF (50 ml.). The resultant mixture was stirred at 50 C for 3 hours, and then to the resulting mixture was added ethyl acetate and water. The organic phase was separated, and then dried over anhydrous a2S04 and concentrated to give 4-bromo- 1 -methoxy-2-(3- methoxypropoxy)benzene (23 g).mol), l-bromo-3-methoxy-propane ( 12.9 g, 84 mmol ), K2CO3 (22 g, 21 53 mmol) and DMF (50 ml.). The resultant mixture was stirred at 50 C for 3 hours, and then to the resulting mixture was added ethyl acetate and water. The organic phase was separated, and then dried over anhydrous a2S04 and concentrated to give 4-bromo- 1 -methoxy-2-(3- methoxypropoxy)benzene (23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; WANG, Jianhua; ZHOU, Chengang; WANG, Yongguang; YANG, Song; (135 pag.)WO2016/71215; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 41789-95-1, Application In Synthesis of 1-(3-Methoxyphenyl)-N-methylmethanamine

General procedure: At 0 C, a solution of 3(4)-bromobenzoyl chloride or 5-bromothiophene-2-carbonyl chloride (1 eq) in CH2Cl2 (2 ml/eq) was added drop wise to a solution of N-methylbenzylamine (1 eq) and triethylamine (1.15 eq) in CH2Cl2 (2 ml/eq). The mixture was kept stirred at 0 C for 3 h and evaporated under reduced pressure. The residue was purified by FC with n-hexane/ethyl acetate as eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Methoxyphenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Xu, Kuiying; Al-Soud, Yaseen A.; Wetzel, Marie; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5978 – 5990;,
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Synthetic Route of 321-28-8, 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. 321-28-8 name is 1-Fluoro-2-methoxybenzene, 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.

(a) Synthesis of STR7 A reaction vessel was charged with 128 g (1.016 mol) of 2-fluoroanisole and 250 ml of chloroform. To this mixture was added dropwise under agitation at room temperature 177 g (1.106 mol) of bromine over the period of at least 3 hours. The reaction liquid was poured into a diluted aqueous solution of NaOH, and the chloroform layer was separated, washed with a solution of edible salt and dried over Glauber’s salt. The solvent was distilled off and the residue was distilled under reduced pressure to obtain 2-fluoro-4-bromoanisole. Yield 192 g (yield rate: 92.3%) b.p. 107-116 C./25-31 mmHg

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Kanto Kagaku Kabushiki Kaisha; US5397504; (1995); A;,
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Electric Literature of 2752-17-2,Some common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, molecular formula is C4H12N2O, 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.

General procedure: The precursor quinoline tetramer acid (100 mg, 0.1 mmol, 2.05 equiv), HBTU (114 mg, 0.3 mmol, 3 equiv), and HOBt (27 mg, 0.2 mmol, 2 equiv) were dissolved in anhydrous DMF under nitrogen. DIEA (173 muL, 1 mmol, 10 equiv) was added and the reaction mixture was stirred at room temperature for 30 min. The diamine (1 equiv) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was poured into water, extracted three times with toluene, dried over Na2SO4, filtered, and concentrated. The crude was purified by silica-gel chromatography eluting with toluene/ethyl acetate 90/10 v/v, yielding the expected compound as a yellow solid.

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Delsuc, Nicolas; Poniman, Legiso; Leger, Jean-Michel; Huc, Ivan; Tetrahedron; vol. 68; 23; (2012); p. 4464 – 4469;,
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Electric Literature of 6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzaldehyde, 0.11 g (1.8 mol) of isopropylamine and 0.2 g of molecular sieves 3A in 10 mL of anhydrous benzene was kept for 24 h at room temperature and filtered. After removal of solvent, 0.44 g (77%) of N-isopropyl-4-(dibromomethyl)benzenecarbimine 13a was obtained as a yellow oily substance.

The chemical industry reduces the impact on the environment during synthesis 4,4-Diethoxybutan-1-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gazizov; Ivanova, S. Yu.; Bagauva; Karimova; Ibragimov, Sh. N.; Musin; Russian Journal of General Chemistry; vol. 85; 9; (2015); p. 2209 – 2211; Zh. Obshch. Khim.; vol. 85; 9; (2015); p. 2209 – 2211;,
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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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7F3N2O

N1-pyrrolidine cyanoguanidine (72 mg, 0.52 mmol) and 4-trifluoro methoxy phenylene diamine (0.1 g, 0.52 mmol) were dissolved in distilled water (10 ml) at room temperature, and then hydrochloric acid(0.1 ml, 1.04 mmol) was added thereto, and stirred with reflux at 110 C. for 2 hr. The reaction mixture was added by 10% potassium hydroxide solution, and then the obtained solid was filtrated under reduced pressure, and was washed with distilled water. The filtrated solid was dried under reduced pressure. The title compound was produced in brown solid phase(20 mg, 12.2%). 1H NMR (600 MHz, CD3OD) delta 7.22 (d, J=8.4 Hz, 1H), 7.13 (s, 1H), 6.90 (d, J=8.4 Hz, 1H), 3.49 (br s, 4H), 1.92 (s, 4H); LC-MS m/z 235.1 [M+1]

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANALL BIOPHARMA CO., LTD.; KIM, Hong Woo; LEE, Ji Sun; HEO, Hye Jin; LEE, Hong Bum; JEONG, Jae Kap; PARK, Ji Hyun; KIM, Seo-il; LEE, Young Woo; US2015/126518; (2015); A1;,
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