Tag: M.W=100-200

Synthetic Route of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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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. 260352-79-2, name is Butyl 2,2-difluorocyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H12F2O2

Referential Example 2 5-(2,2-Difluorocyclopropyl)-lH-pyrazol-3-amine (45) To a solution of MeCN (1.1 g, 16.8 mmol) in THF (60 mL) was added dropwise n-BuLi in THF (11.2 mL, 40.3 mmol) at -78C, and the reaction mixture was stirred at -78 C under N2 for 30 min. Butyl 2,2- difluorocyclopropanecarboxylate (3.0 g, 16.8 mmol) was added at -78 C, and the reaction mixture was allowed to warm to RT over 3 h. The reaction mixture was quenched with water and adjusted to pH 7 with IN HCl. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried (Na2S04), filtered and concentrated in vacuo to afford crude 3-(2,2-difluorocyclopropyl)-3- oxopropanenitrile. A mixture of crude 3-(2,2-difluorocyclopropyl)-3-oxopropanenitrile and hydrazine (2.0 g, 50.4 mmol, 85% pure) in EtOH (30 mL) was stirred at reflux for 16 h. The reaction mixture was concentrated to dryness under reduced pressure. The crude residue was purified by chromatography eluting with an EtO Ac/petroleum ether gradient (12.5 to 100% EtOAc) to afford 2.1 g (78.5%>) of 45 as a yellow solid: 1H NMR (400 MHz, DMSO-d6): delta 11.40 (br s, 1H), 5.26 (s, 1H), 4.80 (br s, 2H), 2.78 – 2.66 (m, 1H), 2.04 – 1.75 (m, 1H), 1.73 – 1.21 (m, 1H); MS (ESI+) m/z = 160.1 [M +1]+.

According to the analysis of related databases, 260352-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
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Application of 14062-24-9, 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. 14062-24-9, name is Ethyl 4-chlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Ethyl alpha-[[(2-chloro-4-pyridinyl)amino]methylene]-(4-chlorophenyl)acetate. A solution of ethyl (4-chlorophenyl)acetate (10.87 g, 54.72 mmol) in 90 mL of ethyl formate was treated with a 60% suspension of NaH in oil (7.0 g, 175 mmol) added in portions. After stirring overnight, the reaction was added to 130 mL of 10% aq. HCl and 70 mL of water. The resulting mixture was extracted with EtOAc (3×50 mL). The pooled EtOAc layers were washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was treated with solid 4-amino-2-chloropyridine (7.08 g) and 100 mL of EtOH. After 48 h at reflux, the reaction was allowed to cool to room temperature. After standing overnight, the precipitate that formed by isolated and washed with EtOH, affording 8.0 g of the desired product

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

Reference:
Patent; Kanner, Richard; US2010/190819; (2010); A1;,
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Reference of 85953-29-3, 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. 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step A. 2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester Under anhydrous conditions a stirred suspension of hexane washed potassium hydride (0.424 g, 10.6 mmol) in 5 mL of dimethylformamide was treated in one portion with 3-methyl pyrazole (0.85 mL, 10.6 mmol). After the gas evolution ceased, 2-chloro-4-fluorobenzoic acid methyl ester (2.0 g, 10.6 mmol) was added to the clear solution. The mixture was heated at 130 C. for 15 minutes, cooled, and partitioned between ethyl acetate and brine. The organic layer was washed with water and brine, and dried over sodium sulfate. Removal of solvent afforded 2.2 g of a yellow oil consisting of a mixture of 3-methyl and 5-methylpyrazole regioisomers. In addition, about 20% of the acid derived from hydrolysis of the ester was detected by analysis of the NMR spectrum of the crude product. The desired 3-methylpyrazole regioisomer was separated from the 5-methyl isomer of Example 22 by flash chromatography (on silica Merck-60, dichloromethane-hexane 2:1) and was isolated as a white solid (1.55 g, 56%). NMR (DMSO-d6, 400 MHz): delta 2.264 (s, 3H, CCH3), 3.845 (s, 3H, OCH3), 6.40 (d, 1H), 7.865 (dd, 1H), 7.93 (d, 1H), 8.00 (s, 1H), 8.535 (d, 1H). MS (EI, m/z): 250/252 [M]+, 219.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-chloro-4-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Home Products Corporation; US6194407; (2001); B1;,
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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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 4-amino-3-methylbenzoate

To a stirred solution of 4-amino-3-methyl-benzoic acid methyl ester (11.55 g, 70 mmol) and 3-bromobenzaldehyde (8.2 mL, 70 mmol) in acetonitrile (150 mL) were added isobutene (17 mL, 242 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (5.2 g, 8.4 mmol). The resulting mixture was stirred at 90 C. for 20 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (8.15 g, 30%) as a light yellow solid: MS (ESI) M+1=388.0 & 390.0.

According to the analysis of related databases, 18595-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Yan, Shixiang; Yun, Hongying; Zhou, Mingwei; US2012/190677; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-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 344-14-9, Safety of Dimethyl 2-fluoromalonate

Example 1; Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10b) 23.01 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (9) over 3 minutes while keeping the internal temperature between 25 C. and 30 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo[3.1.0]hex-2-ene (8) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent: toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of Formula 10a and the compound of Formula lab as a yellow oily material.1H NMR (500 MHz, DMSO-d6): delta 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H).13C NMR (125 MHz, DMSO-d6) delta 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125-59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6); delta -172.43, -172.36. HRMS (ES) m/z:[M+Na]+ calcd for C10H13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1060, 1031, 936, 838, 787, 722, 668, 415 cm-1,

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2011/65934; (2011); A1;,
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Synthetic Route of 4224-69-5, The chemical industry reduces the impact on the environment during synthesis 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, I believe this compound will play a more active role in future production and life.

(7E)-(1R,3R,20R)-1,3-di-(tert-butyldimethylsilyloxy)-2-methylene-9,10-seco-19-nor-20-[(2S)-hydroxy-4-methoxycarbonyl-4-penten-1-yl]-5,7-pregnandiene (10) and (7E)-(1R,3R,20R)-1,3-di-(tert-butyidimethylsilyloxy)-2-methylene-9,10-seco-19-nor-20-[(2R)-hydroxy 4-methoxycarbonyl-4-penten-1-yl]-5,7-pregnandiene (1); To a solution of 9 (25 mg, 425 mumol) in saturated aqueous NH4Cl solution/THF (5:1, 3 mL) were added methylbromomethylacrylate (10 muL, 85 mumol) (commercially available from Sigma-Aldrich) and activated Zn dust (11 mg, 0.17 mmol) at 0 C., and the mixture was stirred at the same temperature for 1.5 hours. The mixture was diluted with EtOAc. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography on silica gel (5% EtOAc/hexanes) to give 10 (5 mg, 7.3 mumol, 57%) and 11 (4 mg, 5.5 mumol, 43%) as colorless oils, respectively. 10: 1H NMR (CDCl3, 400 MHz) delta 6.25(s, 1H, =CH2), 6.21 (d, J=11.2 Hz, 1H, 6-H), 5.84 (d, J=11.2 Hz, 1H, 7-H), 5.67 (s, 1H, =CH2), 4.97 (s, 1H, =CH2), 4.91 (s, 1H, =CH2), 4.42 (m, 2H, 1beta- and 3alpha-H), 3.87 (m, 1H, CH-OH), 3.77 (s, 3H, -CO2CH3), 2.82 (br d, J=11.3, 1H), 2.56-2.44 (m, 3H), 2.40-2.25 (m, 2H), 2.18 (m, 1H), 0.97 (d, J=6.6 Hz, 3H), 0.90 (s, 9H, Si-t-Bu), 0.85 (s, 9H, Si-t-Bu), 0.57 (s, 3H), 0.08, 0.06, 0.05, and 0.02 (each s, each 3H, 4× SiCH3); 13C NMR (CDCl3) delta 168.31, 153.19, 141.28, 137.76, 133.03, 127.92, 122.58, 116.41, 106.44, 72.79, 71.78, 67.85, 57.35, 56.54, 52.28, 47.85, 46.00, 43.93, 41.78, 40.86, 38.72, 33.09, 28.94, 28.08, 26.04, 25.97, 23.62, 22.44, 18.87, 18.45, 18.35, 12.35, -4.67 (SiMe), 4.90 (3× SiMe); exact mass calculated for C40H70O5Si2Na [M+Na]+ 709.4660, found 709.4680. 11: 1H NMR (CDCl3, 400 MHz) delta 6.29 (s, 1H, =CH2), 6.22 (d, J=11.1 Hz, 1H, 6-H), 5.84 (d, J=11.1 Hz, 1H, 7-H), 5.70 (s, 1H, =CH2), 4.98 (s, 1H, =CH2), 4.93 (s, 1H, =CH2), 4.43 (m, 2H, 1beta- and 3alpha-H), 3.90 (m, 1H, CH-OH), 3.79 (s, 3H, -CO2CH3), 2.84 (br d, J=12.1 Hz, 1H), 2.71 (dd, J=13.8, 1.7 Hz, 1H), 2.56-2.42 (m, 2H), 2.34 (m, 1H), 1.03 (d, J=6.4 Hz, 3H), 0.90 (s, 9H, Si-t-Bu), 0.87 (s, 9H, Si-t-Bu), 0.57 (s, 3H), 0.09, 0.08, 0.06, and 0.04 (each s, each 3H, 4× SiCH3); 13C NMR (CDCl3), delta 168.30, 153.17, 141.23, 137.77, 133.04, 128.07, 122.58, 116.41, 106.46, 72.72, 71.83, 69.45, 57.47, 56.43, 52.28, 47.80, 45.91, 44.13, 40.81, 40.27, 38.77, 34.39, 28.93, 28.12, 26.03, 25.98, 23.61, 22.42, 19.55, 18.74, 18.37, 12.29, -4.67 (3× SiMe), -4.88 (SiMe); exact mass calculated for C40H70O5Si2 [M]+ 686.4762, found 686.4789.

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, Methyl 2-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wisconsin Alumni Research Foundation; US2006/223782; (2006); A1;,
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These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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. HPLC of Formula: C8H16ClNO2

To a suspension of (lr,4r)-methyl 4-aminocyclohexanecarboxylate hydrochloride (3.4g, 17.56 mmol) and DIPEA (7.67 mL, 43.9 mmol) in acetonitrile (68.8 mL) was added 4- (4-fluoro-3 -nitrophenyl)-3, 5 -dimethyli soxazole (4.56 g, 19.31 mmol). The (0408) heterogeneous reaction was stirred at 75C for 39 h. The reaction was cooled down to RT and filtered. The filtrate was concetrated in vacuo to give a mixture of oil and orange solid (11 g). The solid was triturated twice with Et20 (50 mL), then z’so-hexanes (50 mL). The solid was dried in vacuo to give 7.5 g of solid which was dried loaded and purified by chromatography column (120g, DCM/MeOH: 100/0 to 95/5) to give (lr,4r)- methyl 4-((4-(3,5-dimethylisoxazol-4-yl)-2-nitrophenyl)amino)cyclohexanecarboxylate (4.29 g, 63%) was isolated as an orange solid; Rt 2.49 min (method 1); m/z 374 (0409) (M+H)+ (ES+).

The synthetic route of Methyl trans-4-aminocyclohexanecarboxylate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; ONIONS, Stuart Thomas; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; BROWN, Richard James; SMYTH, Don; HARBOTTLE, Gareth; (376 pag.)WO2018/73586; (2018); A1;,
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Reference of 1188911-72-9, These common heterocyclic compound, 1188911-72-9, name is Methyl 3,3,3-trifluoro-2,2-dimethylpropanoate, 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 mixture of acetonitrile (3.32 mL, 97 mmol) in THF (300 mL) cooled to -78 C. was added n-BuLi (56.4 mL, 141 mmol).The mixture was stirred at -30 C. for 30 min. Then to the mixture was added methyl 3,3,3-trifluoro-2,2-dimethylpropanoate (15 g, 88 mmol) dropwise. The mixture was stirred at 25 C. for 10 h. The mixture was quenched with NH4Cl (aq) and extracted with DCM/MeOH (10:1). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=10:1). All fractions found to contain product by TLC (PE/EA=5:1, Rf=0.6) were combined and concentrated to yield a light yellow solid of 5,5,5-trifluoro-4,4-dimethyl-3-oxopentanenitrile (5 g, 27.9 mmol, 31.7% yield): 1H NMR (400 MHz, CDCl3) delta: 3.75 (s, 2H), 1.41 (s, 6H).

Statistics shows that Methyl 3,3,3-trifluoro-2,2-dimethylpropanoate is playing an increasingly important role. we look forward to future research findings about 1188911-72-9.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; EIDAM, Hilary Schenck; Raha, Kaushik; Gong, Zhen; Guan, Huiping; Wu, Chengde; Yang, Haiying; Yu, Haiyu; Zhang, Zhiliu; CHEUNG, Mui; US2014/275111; (2014); A1;,
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Synthetic Route of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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 mixture of methyl 2-amino-4-methoxybenzoate (5.4 g, 30.0 mmol) and chloroacetonitrile (2.8 mL, 45.0 mmol) was added anhydrous hydrogen chloride (4M solution in 1,4-dioxane, 20.0 mL, 80 mmol) and the reaction mixture was stirred at 50 C for 30 minutes. After cooling it to room temperature the resulting slurry was diluted with diethyl ether (100 mL) and the stirring was continued for an additional 30 minutes. The off-white precipitate was collected by filtration, washed with diethyl ether and dried in vacuo to provide 2-(chloromethyl)-7-(methyloxy)quinazolin-4-ol hydrochloride (7.5 g, 96%). MS (EI) for C10H9ClN2O2: 225 (MH+).

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUHR, Chris, Allen; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; TSUHAKI, Amy, Lew; MA, Sunghoon; MANALO, Jean-claire, Limun; NG, Stephanie; PETO, Csaba, J.; RICE Kenneth D.; TSANG, Tsze, H.; ZAHARIA, Cristiana, A.; WO2010/135524; (2010); A1;,
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