Tag: M.W=100-200

Synthetic Route of 17994-94-4, These common heterocyclic compound, 17994-94-4, name is Methyl 7-aminoheptanoate 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.

7-(4-Butyl-benzylamino)-heptanoic acid methyl ester. A solution of 7-amino-heptanoic acid methyl ester hydrochloride, prepared of Preparation 1, (1.12 g, 5.9 mmol), 4-butyl-benzaldehyde (0.915 g, 5.65 mmol), and triethylamine (0.83 mL, 5.98 mmol) in 20 mL MeOH was stirred at room temperature for 3 hours. After cooling to 0 C., NaBH4 (0.342 g, 9.04 mmol) was added and the reaction was stirred for 15 minutes at room temperature. The mixture was quenched with 1:1 NaHCO3:H2O and the MeOH was removed in vacuo. The resulting residue was diluted with CH2Cl2 and the organic solution was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound of Step A (1.4 g). 1H NMR (400 MHz, CDCl3) delta 7.08-7.38 (m, 4H), 3.62 (s, 2H), 3.29 (s, 3H), 2.52-2.66 (m, 4H), 2.25 (t, 2H), 1.53-1.63 (m, 6H), 1.25-1.40 (m, 6H), 0.85 (t, 3H); MS 306 (M+1).

Statistics shows that Methyl 7-aminoheptanoate hydrochloride is playing an increasingly important role. we look forward to future research findings about 17994-94-4.

Reference:
Patent; Pfizer Inc.; US2005/203086; (2005); A1;,
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Related Products of 23680-40-2, 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. 23680-40-2, name is Methyl 3-bromopropiolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added to atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, silica gel (150 mg) was added under flow of nitrogen and the mixture wasstirred at reflux for 2 h. After removal of the solvent and filtration, a product 4 was purified by silica gelcolumn chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.

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

Reference:
Article; Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya; Tetrahedron Letters; vol. 55; 38; (2014); p. 5302 – 5305;,
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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. 89-71-4, name is Methyl 2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H10O2

To a solution of methyl 2-methylbenzoate (5g, 0. 033mol) in carbon tetrachloride (85ml) was added n-bromosuccinimide (5.93g, 0. 033mol) and benzoyl peroxide (0.22g, 0. 9mol). The reaction was refluxed for 4 hr. The reaction was cooled to room temperature. The white precipitate was filtered and the solvent removed. The oil was dissolved in ET2O and cooled to-78C The product precipitated and collected yielding v (5. 86G, 77%).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHROMA THERAPEUTICS LIMITED; WO2004/101506; (2004); A1;,
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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. 4519-46-4, name is Methyl 2-bromoacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4519-46-4

To a solution of methyl 2-bromo-2-propenoate (452 mg, 2.74 mmol) (for a synthesis see Rachon, J.; Goedken, V.; Walborsky, H. J. Org. Chem. (1989), 54(5), 1006) in degassed tetrahydrofuran (10 ml) under an argon atmosphere was added [2- (methyloxy)-8-quinolinyl]boronic acid (506 mg, 2.49 mmol), bis(tri-t- butylphosphine)palladium (0) (25 mg, 0.05 mmol), bis(dibenzylideneacetone)palladium(0) (23 mg, 0.025 mmol) and potassium fluoride (477 mg, 8.217 mmol). The reaction was heated at 7O0C for 24 hours and then treated with water and dichloromethane. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4) and the solvent removed under reduced pressure. The residue was subjected to chromatography on silica gel using a ethyl acetate-hexane gradient. This provided the desired compound as a yellow solid (381 mg, 63%).MS (ES+) m/z 244 (MH+, 100%), 212 (80%).

The synthetic route of 4519-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/128962; (2008); A1;,
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Reference of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: All microwave reactions were carried out in a capped (10 mL) microwave-vessel (Borosilicate glass vial sealed) that was placed in a microwave cavity. The pressure was set at 17 bar (average of an effective pressure = 4 bar) with power 75 W. DIEA (3.4 g, 3.4 mmol) was added to a solution of either 2,5-difluoro-4-(pyrrolidin-1-yl) benzoylchloride 12 (0.83 g, 3.4 mmol) or 2,5-difluoro-4-(pyrrolidin-1-yl)benzothioyl chloride 13 (0.88 g, 3.4 mmol) and ethyl-3-(diethylamino)acrylate 14 (0.45 g, 3.1 mmol) in acetonitrile (5 mL). The mixture reaction was held at 100 C for 20 min. After the reaction vessel was cooled to room temperature, the crude product was diluted with water (10 mL) and extracted with ethyl acetate(3 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered, evaporated and purified by a flash column chromatography (eluent n-hexane: acetone, 3:1)to give the titled compounds. Ethyl-2-(2,5-difluoro-4-(pyrrolidin-1-yl)benzoyl)-3-(dimethylamino) acrylate (15)Yellow oil (Rf = 0.3), Yield 85%. IR (KBr) numax in cm-1:2993 (C-H, Ar), 2953 (C-H), 1760 (C=O), 1692 (C=O),1654 (C=C, Ar), 1592 (C-N). 1H NMR (400 MHz, DMSOd6):delta = 7.77 (1H, s, CH), 7.32 (1H, d, J = 5.0 Hz, CH-Ar),6.88 (1H, d, J = 5.2 Hz, CH-Ar), 4.2 (2H, q, J = 7.1 Hz,CH2), 3.47-3.42 (4H, m, 2CH2), 3.1 (6H, s, 2CH3), 2.01-1.97 (4H, m, 2CH2), 1.32 (3H, t, J = 4.2 Hz, CH3).

The chemical industry reduces the impact on the environment during synthesis Ethyl 3-(dimethylamino)acrylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (2020);,
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90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, belongs to esters-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. name: Sodium 3-methoxy-3-oxopropane-1-sulfinate

ADMSO (0.5 mL) solution of Example 318 (20 mg, 39 tmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (20 mg, 116 tmol) and copper(I) iodide (22 mg, 116.imol) was heated in a sealed safety vial at 120 C for 4.5 h. The resulting mixture wasdiluted with MeOH (1 mL) and filtered. The filtrate was purified via preparative LC/MS(Condition A: Gradient: 20-60% B over 20 minutes, then a 5-minute hold at 100% B) to give (R)-methyl 3 -((3 -(1 -((3 -chloro-6-(2-(2-hydroxypropan-2-yl)pyrimidin-5 -yl)quinolin4-yl)amino)ethyl)-4-fluorophenyl)sulfonyl)propanoate (3 mg, 13% yield). LC/MS (M+H): 587; LC retention time: 1.87 mm (Method A). ?H NMR (500 MFIz, DMSO-d6) oe 9.26 (s, 2H), 8.75 (s, 1H), 8.49 (s, 1H), 8.18-8.11 (m, 2H), 8.00 (d,J=8.8 Hz, 1H), 7.80(br. s., 1H), 7.44 (t, J=9.3 Hz, 1H), 6.93 (d, J=8.5 Hz, 1H), 5.86-5.78 (m, 1H), 2.42-2.32 (m, 4H), 1.71 (d, J=6.7 Hz, 3H), 1.56 (s, 6H).

The synthetic route of 90030-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; XIAO, Hai-Yun; DHAR, T. G. Murali; LI, Ning; DUAN, Jingwu; JIANG, Bin; LU, Zhonghui; NGU, Khehyong; PITTS, William J.; TINO, Joseph; (402 pag.)WO2017/23905; (2017); A1;,
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Related Products of 20372-66-1, A common heterocyclic compound, 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, molecular formula is C8H5F3O2, 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.

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals; 950.61 mg; 5 mmol; 1 eq.), sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) and tetrabutylammonium bromide (2 014.82 mg; 6.25 mmol; 1.25 eq.) were dissolved in DMF (10 mL) . The resulting mixture was heated at 6O0C overnight. As the reaction was not complete, sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) was added and the mixture was stirred at 6O0C for additiona 24 h. The resulting dark pink solution was diluted with EtOAc and washed with brine several times. It was dried over MgSO4, filtrated and evaporated, resulting into a sticky dark red oil, which was purified by flash chromatography (Sitheta2 100 g, EtOAc / c-hex 1 :9 until 1 :1 ), affording the title product. 1H NMR (DMSO-d6, 300 MHz) delta 7.77 (dd, J = 5.45, 8.41 Hz, 1 H), 7.42 (dd, J = 4.99, 8.88 Hz, 1 H), 3.96 (s, 3H). LC/MS (Method A): 463.2 (M-H)”; 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

The synthetic route of 20372-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6933-47-7,Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

Synthesis 184-(3,5-Dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019)Step (i): Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3)1A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2- methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCI (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3 x 15 mL), dried over MgS04, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2- methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)” (ES”). 1H NMR (400 MHz, CDCI3) delta: 7.97 (1 H, s), 7.80 (3H, m), 7.54 (1 H, dd), 7.51 (1 H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; CORCORAN, Jonathan Patrick Thomas; KALINDJIAN, Sarkis Barret; BORTHWICK, Alan David; ADAMS, David Reginald; BROWN, Jane Theresa; TADDEI, David Michel Adrien; SHIERS, Jason, John; WO2011/27106; (2011); A1;,
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36692-49-6, name is Methyl 3,4-diaminobenzoate, belongs to esters-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. Product Details of 36692-49-6

A mixture of (4-tert-butyl-phenoxy)acetic acid (300 mg, 1.4 mmol), 3,4-diaminobenzoic acid methyl ester (300 mg, 1.4 mmol) in PPSE (4.8 mL) was heated at 160 C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane=1:9-4:6) to afford 2-2,4-tert-butyl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (547 mg, 80% yield). 1H-NMR (CDCl3, 300 MHz) 8.39 (1H, s, aromatic), 8.03 (1H, d, J=8.1 Hz, aromatic), 7.66 (1H, d, J=7.8 Hz, aromatic), 7.27 (2H, d, J=8.4 Hz, aromatic), 6.88 (2H, d, J=8.7 Hz, aromatic), 5.43 (2H, s, OCH2), 3.95 (3H, s, OCH3), 1.27 (9H, s, t-butyl), NH not detected.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
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These common heterocyclic compound, 4492-02-8, name is Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate, 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. Formula: C10H14N2O2

Example 1 IndazoLe-3-Carboxylic Acid A mixture of 4,5,6,7-tetrahydroindazole-3-carboxylic acid ethyl ester (21.0 g, 108 mmol), 5% palladium on carbon (7.0 g solid, 3.29 mmol of Pd), and 210 mL of cymene was heated to reflux for 38 hours. At this point complete conversion to the indazole-3-carboxylic acid ethyl ester was shown by TLC (silica gel, 3:1 ethyl acetate-heptane). The reaction was cooled to 120 C. and the 5% palladium on carbon was removed by filtration.

The synthetic route of Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US5914405; (1999); A;,
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