Ethers-buliding-blocks

33311-29-4, name is 4-(2-Methoxyethoxy)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C9H13NO2

b. 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid [4-(2-methoxy-ethoxy)-phenyl]-amide; A mixture of 4-(6,7-dimethoxy-quinazolin-4-yl)-piperidine-1-carbonyl chloride (18 mg, 0.0536 mmol), as prepared in Example 3a, 4-(2-methoxy-ethoxy)-phenylamine (8.9 mg, 0.0533 mmol), as prepared in the previous step, and triethylamine (14 muL, 0.1 mmol) was stirred in DMSO (0.5 mL) at 50 C. overnight. The reaction was then cooled to RT, partitioned between EtOAc (10 mL) and H2O (10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by prep tlc (1:9 MeOH/DCM) afforded the title compound as a brown solid (5.7 mg, 23%). 1H NMR (300 MHz, CDCl3) delta 9.16 (s, 1H), 7.28-7.25 (m, 4H), 6.89 (m, 2H), 6.33 (br s, NH), 4.29-4.24 (m, 2H), 4.12-4.07 (m, 8H), 3.74 (m, 2H), 3.59 (m, 1H), 3.45 (s, 3H), 3.17 (m, 2H), 2.22-2.08 (m, 2H), 2.05-1.97 (m, 2H); LC/MS (ESI): calcd mass 466.2, found 467.4 [M+1]+.

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baindur, Nand; Gaul, Michael David; Kreutter, Kevin Douglas; Baumann, Christian Andrew; Kim, Alexander J.; Xu, Guozhang; Tuman, Robert W.; Johnson, Dana L.; US2006/281772; (2006); A1;,
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Related Products of 707-07-3, 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. 707-07-3, name is (Trimethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

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, (Trimethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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Application of 16452-01-0, These common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, 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 705,5-dimethyl-3-[6-(7-methylspiro[2H-benzofuran-3 ‘-cyclopropanel-4-yl)oxy-3-pyridyllimidazoli2.4- dione To a solution of triphosgene (30 mg, O.lmmol) in dry DCM (1ml) at OPC, under nitrogen atmosphere, DIPEA (0.175 ml, 1.0 mmol) was added followed by the addition (slowly added) of a solution of 6-(7- methylspiro[2H-benzofuran-3,l’-cyclopropane]-4-yl)oxypyridin-3-amine (Intermediate 158, 27 mg, 0.1 mmol) in dry DCM (2ml) and the reaction mixture was stirred for 15 minutes at the same temperature. After that a solution of Methyl 2-amino-2-methylpropanoate hydrochloride (30mg, 0.2mmol) in dry DCM (2ml) was added and the reaction mixture was stirred for 30 minutes at OPC. The reaction was quenched with a 1M aqueous solution of HCI (5ml), diluted with DCM (10ml) and two phases were separated. The organic layer was washed with brine (10ml), dried (IS^SC^), filtered and evaporated affording the urea intermediate as yellow foam.The urea was dissolved in MeOH (5ml), NaOMe (lOmg, 0.19 mmol) was added and the reaction mixture was stirred for 15 minutes at room temperature. The reaction was quenched with an aqueous saturated solution of ammonium chloride (20ml) and diluted with ethyl acetate (40ml). Two phases were separated and the organic layer was dried (Na2S04), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a lOg SNAP column and cyclohexane/ethyl acetate 75:25 to cyclohexane/ethyl acetate 25:75 as eluents affording the title compound (23mg) as a white solid.1H-NMR (400 MHz, DMSO-d6) delta ppm: 8.62 (1H, s), 8.14 (1H, d), 7.86 (1H, dd), 7.05 (1H, d), 6.92 (1H, d), 6.43 (1H, d), 4.44 (2H, s), 2.14 (3H, s), 1.40 (6H, s), 1.08-1.13 (2H, m), 0.96 (3H, t), 0.85-0.90 (2H, m). LC/MS: QC_3_MIN: Rt = 2.016 min; 380 [M+H]+.

Statistics shows that 3-Methoxy-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 16452-01-0.

Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; ALVARO, Giuseppe; DAMBRUOSO, Paolo; MARASCO, Agostino; TOMMASI, Simona; DECOR, Anne; LARGE, Charles; WO2012/76877; (2012); A1;,
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Related Products of 2062-98-8, The chemical industry reduces the impact on the environment during synthesis 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, I believe this compound will play a more active role in future production and life.

[0097] Compound (2b) (620 g) was put into a 2L autoclave made of hastelloy C and stirred, while bubbling nitrogen gas. While maintaining the internal temperature at from 25 to 35 DEG C, compound (4b) (1830 g) was dropwise added over a period of 8 hours thereto. After completion of the dropwise addition, bubbling of nitrogen gas was further continued to remove HF and excess compound (4b) and to obtain 2245 g of compound (3b). Using compound (3b) (1800 g), a fluorination reaction was carried out in the same manner as in Example 2 to obtain compound (1b) in a yield of 69%.

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, Perfluoro(2-methyl-3-oxahexanoyl) fluoride, other downstream synthetic routes, hurry up and to see.

Reference:
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Electric Literature of 3616-56-6, These common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, 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 269 2-[3-(2-Dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine A mixture of 1.1 g., (0.005 mole) of 2-(3-aminophenyl)oxazolo[4,5-b]pyridine and 50 ml. of ethanol is reacted with dimethylaminoacetaldehyde [from 0.96 g. (0.006 mole) dimethylaminoacetaldehyde diethylacetal]by gentle heating to complete the intermediate Schiff base formation. The mixture is then cooled and 60 mg., (0.0015 mole) of sodium borohydride is added, and the mixture allowed to stir overnight at room temperature. Water is added, the solvents are removed in vacuo, and the residue is distributed between water and methylene chloride. The organic layer is dried and concentrated in vacuo to give crude 2-[3-(2-dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine, purified via column chromatography using an alumina column with an ethylacetate-ether mixture (v/v 0-60percent ethylacetate) as eluant.

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4038396; (1977); A;,
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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. 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 57478-19-0

4-Amino-4′-trifluoromethyldiphenyl ether (15 g.) was added in small portions to a stirred solution of phosgene in toluene (180 ml, 12.5% solution) at 0. The mixture was refluxed, with stirring, for 3 hours. The solvent was removed in vacuo. Distillation gave 4-(4′-trifluoromethyl-phenoxy)phenylisocyanate as a pale yellow oil (8.1 g, boiling point 110-114, 0.5 mm).

According to the analysis of related databases, 57478-19-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burroughs Wellcome Co.; US4816460; (1989); A;,
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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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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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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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Synthetic Route of 91-16-7,Some common heterocyclic compound, 91-16-7, name is 1,2-Dimethoxybenzene, molecular formula is C8H10O2, 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.

That is,A 30 mL Schlenk tube was charged with 1,2-dimethoxybenzene (76 muL, 0.6 mmol)GO containing 50.66 w% of oxygen (100 mg)And boron trifluoride-ethyl ether complex (2.0 mL, 16.2 mmol) were charged,And reacted at 60 C. for 8 hours.Here, in GO,The amount of potassium permanganate to be used at the time of synthesis of GO is set to 5 times the amount of potassium permanganate used in Example 7 is used.After the reaction, the GO was crushed with ultrasonic waves, and the filtrate was suction filtered while washing with chloroform, the filtrate was separated with chloroform and water, the organic layer was filtered with folded folded paper and the solvent was distilled off under reduced pressure with an evaporator And dried under reduced pressure. The yield was 83%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dimethoxybenzene, its application will become more common.

Reference:
Patent; OKAYAMA UNIVERSITY; NISHINA, YUTA; MORIOKU, KUMIKA; (13 pag.)JP2017/31106; (2017); A;,
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