Author: Jessica.F

Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: An autoclave was filled with catalyst (1 molpercent based on the molar amount of amine), flushed with argon and topped up with a solution of amine (0.1 mol) and orthocarboxylic acid ester (0.11-0.3mol) in 10 ml of methanol (or ethanol) and 0.5 ml of a 0.2 M solution of anhydrous ptoluenesulphonic acid in methanol (or ethanol). The mixture was heated to 120°C and hydrogen was injected to 40 bar and then the mixture was stirred at a constant pressure until hydrogen absorption could no longer be detected (0.2 – 6 h). After being filtered off from the catalyst, the filtrate was distilled.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVONIK DEGUSSA GMBH; KADYROV, Renat; (19 pag.)WO2017/133913; (2017); A1;,
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Electric Literature of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

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-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,5-Dimethoxyphenylacetylene

Compound 3-iodo-1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole 4-formamidine 2c (2.7 g, 7.3 mmol), 1-ethynyl-3,5-dimethoxybenzene (1.78 g, 11 mmol), triethylamine (2.2 g, 21.9 mmol), bis (triphenylphosphonium) palladium chloride (512 mg, 0.73 mmol) and anhydrous tetrahydrofuran (70 mL) were mixed, deoxygenated, and stirred at room temperature under an argon atmosphere for 15 hours.The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / petroleum ether = 10/1 to 2/1) to give the target product 3-((3,5-dimethoxyphenyl) acetylene Yl) -1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole-4-carboxamide 2d (1.5 g, yellow solid), yield: 51%.

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H11BrO2

Example 7 (+-)-3-{1-[2-(2-Methoxyethoxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol To a solution of (+-)-3-(trans-3,4-dimethylpiperidinyl)phenol (60 mg, 0.29 mmol) in N,N-dimethylformamide (5.0 mL) at room temperature was added sodium hydrogencarbonate (27 mg, 0.32 mmol), and 1-bromo-2-(2-methoxyethoxy)ethane (59 mg, 0.32 mmol). The solution was heated at 120 C. for 1 hour, cooled and then water (10 mL) was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. This was purified by preparative HPLC on a Dynamax column, 42*250 mm; flow 8.0 mL min-1; employing U.V. detection at 275 nm; eluant gradient of acetonitrile:0.05 M aqueous ammonium acetate solution (90:10 to 10:90) to afford the title compound (71 mg, 80%) as its acetate salt. 1H-NMR (data for the acetate salt): 0.82 (d, 3H), 1.35 (s, 3H), 1.72 (m, 1H), 2.03-2.10 (m, 4H), 2.38 (m, 1H), 2.81-3.13 (m, 6H), 3.40 (s, 3H), 3.50-3.63 (m, 4H), 3.70-3.78 (m, 2H), 6.68 (m, 1H), 6.81-6.82 (m, 2H), 7.18 (t, 1H). MS (TSI+): m/z [MH+] 308.3; C18H29NO3+H requires 308.2.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6518282; (2003); B1;,
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Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

A) [3-(trifluoromethoxy)phenyl]hydrazine hydrochloride 3-(Trifluoromethoxy)aniline (3.68 ml) was dissolved in 6 M hydrochloric acid (71 ml), and an aqueous solution (4.7 ml) of sodium nitrite (2.08 g) was added dropwise over 20 min at -5° C. Tin (II) chloride (1.954 ml) was dissolved in 6 M hydrochloric acid (25 ml), and the solution was cooled to -5° C., and added quickly to the above-mentioned reaction mixture at -5° C. The mixture was stirred at -5° C. for 2 hr, and the precipitated solid was collected by filtration, washed with 0.1M hydrochloric acid, and dried under reduced pressure to give the title compound (2.72 g). 1H NMR (300 MHz, CDCl3) delta 6.81-7.03 (3H, m), 7.41 (1H, t, J=8.3 Hz), 8.64 (1H, br. s.), 10.35 (2H, br. s.)

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yoshikawa, Masato; Suzuki, Shinkichi; Hasui, Tomoaki; Fushimi, Makoto; Kunitomo, Jun; Kamisaki, Haruhi; Taniguchi, Takahiko; US2013/150344; (2013); A1;,
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22236-08-4, name is 3-(Difluoromethoxy)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. SDS of cas: 22236-08-4

General procedure: The synthesis was carried out by using the synthetic method a. To a solution of 2-picolinic acid (0.871 g,7.08 mmol), N-hydroxybenzotriazolehydrate (HOBt.H2O,1.084 g, 7.08 mmol), diisopropylethylamine(DIPEA, 1.83 g, 14.17mmol) and N-(3-methylaminopropyl)-N?-ethylcarbodiimidehydrochloride (EDCHCl, 2.036 g, 10.63mmol) in anhydrous 1,4-dioxane (60 mL) was added 3-fluoro-3-methoxyanilline (1.00 g, 7.08 mmol) at room temperature. The mixture was heated to 50 oC and stirred overnight. To the reaction mixture was added 300 mL of dichloromethane, and sequentially washed with water (3 x100 mL). After the organic layer was separated and concentrated, the reaction mixture was purified by silica-gel chromatography (hexane/ethyl acetate) to give the product as a pale-yellow solid (1.559 g, 6.33mmol, 89.4% yield).

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhaoda; Kil, Kun-Eek; Poutiainen, Pekka; Choi, Ji-Kyung; Kang, Hye-Jin; Huang, Xi-Ping; Roth, Bryan L.; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3956 – 3960;,
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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. 34967-24-3, name is 3,5-Dimethoxybenzyl amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

General procedure: Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min.

According to the analysis of related databases, 34967-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abate, Mario; Bifulco, Maurizio; Buonocore, Michela; Ciaglia, Elena; Covelli, Verdiana; D’Ursi, Anna Maria; Gazzerro, Patrizia; Grimaldi, Manuela; Randino, Rosario; Rodriquez, Manuela; Scrima, Mario; Stillitano, Ilaria; Tosco, Alessandra; Bioorganic Chemistry; (2020);,
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Synthetic Route of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 500 mL dry flask was charged with 2-bromo-5-fluoro-4-isopropylanisole (compound of formula 4, Scheme 3) (24.6 g, 0.1 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri-isopropylborate (32 mL, 0.14 mol) was added. The mixture was cooled to -80 C. Then 10 M n-BuLi in hexanes (12.5 mL, 0.125 mol) was added slowly, maintaining a temperature below -55C. Thirty minutes after completion of the n-BuLi addition, the reaction was warmed to -35C and quenched into 3 M H2S04 solution (75 mL, 0.225 mol). DIPE (200 mL) was added to the mixture to dilute the organic layer. The mixture was stirred (15 min) and the aqueous layerwas cut away. The organic layerwas washed with 3.0 M H2S04 (75 mL). The organic phase was extracted three times with 1 M NaOH (200 mL first and then 50 mL and 50 mL). The three NaOH extractions were combined, diluted with 2-propanol (85 mL), and cooled to 15 “C. Then the solution was slowly acidified to pH ~ 2 using 3 M H2SO4 (70 mL) while maintaining temperature at 15-20 C. The resulting slurry was stirred for 1 hour and then filtered. The filter cake was washed with water (3 x 30 mL) and dried under an air flow for 1 day. The filtered solid was placed in an oven under vacuum at 50 C for 2-3 days to decompose a diaryl impurity and to dry the solid. The white crystalline solid was isolated to yield boronic acid of formula 5 (Scheme 3) (19.23 g, 91 %): mp 100-102 C; H NMR (CDCI3) delta 1.25 (d, J = 6.9 Hz, 6H), 3.17 (sept, J = 6.9 Hz, 1 H), 3.88 (s, 3H), 5.83 (S, 2H), 6.59 (d, J = 12 4 Hz, 1 H), 7.72 (d, J = 6.6 Hz, 1 H). The impurity 5-ethyl-4-fluoro-2-methoxyphenylboronic acid (-4%), which is formed from 1-bromo-5-ethyl-4-fluoro- 2-methoxybenzene (BrMET) present in the starting material under the conditions described in Step 4, was detected in the product.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H13BrO

Magnesium (317.2 mg, 13.05 mmol) was suspended in 5 mL of ether, a solution of 2.30 mL (13.0 mmol) of 3-benzyloxypropyl bromide in 7 mL of ether was dropped into the suspension over 10 minutes, a flake of iodine was added thereto and the mixture was heated to reflux for 1 hour. The reaction mixture was cooled with an ice-methanol bath, a solution of 5.1 mg (0.011 mmol) of N-methoxy-N-methyl-(1-methylindole)-2-carboxamide in tetrahydrofuran was added thereto and the mixture was stirred at 0°C for 2 hours. Ice water was added to the reaction solution and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ether. The organic layer was washed with water and a saturated aqueous saline solutio dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate = 8/1) to give 0.79 g (54percent) of 2-(4-benzyloxy-1-oxobutyl)-1-methylindole.1H-NMR(270MHz, DMSO-d6, delta); 2.09(m, 2H), 3.10(t, J=7.3Hz, 2H), 3.58(t, J=6.1Hz, 2H), 4.05(s, 3H), 4.50(s, 2H), 7.15(m, 1H), 7.26-7.39(m, 8H), 7.69(dd, J=1.0Hz, 8.3Hz, 1H). Fab-MS(m/z); 308[M+1]+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54314-84-0.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1464645; (2004); A1;,
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Reference of 93919-56-3, 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. 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.

6-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester To a stirred solution of 6-methoxy-5-formyl-2-naphthoic acid methyl ester (1.09 g, 4.46 mmol) in EtOH (40 ML) at room temperature was added 4-trifluoromethoxy-benzyl amine (0.749 ML, 4.91 mmol) followed by HOAc (0.255 ML, 4.46 mmol).After 10 min. at this temperature, sodium cyanoborohydride (0.420 g, 6.69 mmol) was added, and reaction was continued stirring at rt for 4 h.After 1 h at this temperature, the reaction was heated to 45 C. for 2 h.The solution was quenched with sat. aq. NaHCO3 (20 ML) and then extracted with EtOAc (200 ML).The organic layer was washed with brine (20 ML) and dried (MgSO4).After concentration, the residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient) to afford the product (0.780 g, 42%) as a solid; 1H NMR (DMSO-d6) delta3.77 (s, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.07 (s, 2H), 7.26 (d, J =8.0 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.48 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 8.06 (d, J=5.2 Hz, 1H), 8.08 (d, J=5.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H); mass spectrum [(+) El], m/z 420 (M+H)+.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2004/127570; (2004); A1;,
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