Tag: M.W=100-200

Some common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, molecular formula is C7H15NO2, 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. 5616-81-9

B. Synthesis of Intermediate B5 Intermediate B5 was synthesized using the method reported in Bioorganic & Medicinal Chemistry Letters 2008, 18, 3902-3905, with modifications as shown in the above scheme. Observed ESI HRMS: m/z 992.3193 [M+H]+. The 1H NMR spectrum of B5 is shown in FIG. 42a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5616-81-9, its application will become more common.

Reference:
Patent; Sirenas LLC; MACHERLA, Venkat Rami Reddy; SCHAMMEL, Alexander Wayne; USUI, Ippei; STOUT, Elizabeth Paige; BEVERAGE, Jacob Neal; LEE, Bryan Junn; COHEN, Steven Bruce; (304 pag.)US2017/15710; (2017); A1;,
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349-43-9, A common heterocyclic compound, 349-43-9, name is Ethyl 2-fluoropropionate, molecular formula is C5H9FO2, 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.

LDA (2.0 M, 36 mL) was added to the solution of ethyl 2- fluoropropanate (7.23 g) and acetaldehyde (13.5 mL) in ether (100 mL) at-78 ¡ãC. After the addition finished the reaction flask was kept in ice bath and gradually warm to room temperature. The reaction was quenched with aqueous ammonium chloride after overnight stirring. The aqueous phase was extracted with ether and the combined organic phase was dried over sodium sulfate. The solvent was stripped off and the residue was distilled in vacuo to give 541-YJ-97 (4.22 g).

The synthetic route of 349-43-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI CO. LTD.; WO2003/76424; (2003); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3196-15-4 as follows. 3196-15-4

Step 4: methyl 2-(6-(azetidin-1-carbonyl)-2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)butanoate To a solution of N-(6-(azetidin-1-carbonyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide (91 mg, 0.26 mmol), prepared in Step 3, in N,N-dimethylformamide (1.0 mL) were added potassium carbonate (108 mg, 0.78 mmol) and methyl 2-bromobutyrate (45 uL, 0.39 mmol). The reaction mixture was stirred at 80 C. overnight and then cooled to room temperature. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. Diisopropyl ether and ethyl acetate were added to the filtrate. The resulting mixture was stirred for 5 minutes and then filtered. The resulting solid was washed with diisopropyl ether, and then dried under reduced pressure to give 61 mg of the titled compound as a white solid (Yield: 52%). 1H NMR (CDCl3, 400 MHz) delta 8.18 (d, 2H), 8.01 (s, 1H), 7.73-7.88 (m, 2H), 7.26-7.31 (m, 2H), 5.54-5.62 (m, 1H), 4.27-4.38 (m, 3H), 3.66 (s, 3H), 3.13 (m, 1H), 2.37-2.54 (m, 7H), 0.90 (t, 3H)

According to the analysis of related databases, 3196-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
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10601-80-6, 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (2.00 g, 50.6 mmol, 60%) was added to a solution of ethyl formate (10.13 g, 168.7 mmol) in tetrahydrofuran while maintaining the internal temperature below 0 C. Then, ethyl 3,3-diethoxy propionate (5.00 g, 33.75 mmol) was added dropwise to the reaction mixture and stirred for 24 h at ambient temperature. After confirming that the reaction was complete by using TLC analysis, the reaction was quenched with 20 mL water and the tetrahydrofuran was removed under reduced pressure. The mixture was extracted with ethyl acetate and then brine. The organic phase was dried over Na2SO4 overnight and the solvent was removed in vacuo to give the title compound 14.

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Reference:
Article; Zhao, Shizhen; Zhang, Xiangqian; Wei, Peng; Su, Xin; Zhao, Liyu; Wu, Mengya; Hao, Chenzhou; Liu, Chunchi; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 96 – 107;,
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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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., 89-91-8

General procedure: To a solution of diisopropylamine (1.5 eq.) in THF (1.5M) at ooc under N2 was added nBuli(1.4eq., 1.6M in hexane) and the mixture was stirred for 20 min. The LOA was cooled to -80C20 and TMSCI (1.4 eq.) was added followed by the methyl ester (1 eq.). The reaction was allowedto reach ooc over 3 h, brought to rt and stirred for 30 min. Pentane was added and the whiteprecipitate filtered off over celite. The solvent was removed under reduced pressure. Purificationif necessary was performed by bulb-to-bulb distillation.

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Reference:
Patent; SANDOZ AG; HOEFERL-PRANTZ, Kathrin; FELZMANN, Wolfgang; WILHELM, Thorsten; BENITO-GARAGORRI, David; WO2013/189980; (2013); A1;,
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61367-07-5, 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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

EDCI (19 mg, 0.097 mmol), HOBt (13 mg, 0.097 mmol), and DIEA (0.034 mL, 0.195 mmol) were added to a solution of carboxylic acid intermediate 13 (30 mg, 0.065 mmol) dissolved in DCM. After 10 minutes, methyl trans-4-aminocyclohexanecarboxylate hydrochloride (25 mg, 0.13 mmol) and a catalytic amount of DMAP were added. After stirring overnight, the solvent was removed and the crude product was purified by column chromatography to give the 30 mg of intermediate 18 as a white solid.

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Reference:
Patent; Sanofi; The Regents of the University of Michigan; US2012/289494; (2012); 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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., 33993-24-7

EXAMPLE 37; Synthesis of cyclopropyl(2-isopropy]pyrazolo[l,5-a]pyridin-3-yl)methanone; 2-isopropyl-pyrazolo[l,5-a]pyridine (2.00 g, 12.4 mmol) was dissolved in cyclopropyl anhydride (8.00 g, 51.9 mmol). Concentrated H2SO4 (3 drops) was added at room temperature and the mixture was then heated to 140 0C for 28 hours. The mixture was then cooled to 0 0C, diluted with H2O (10 mL) and 50 % NaOH (aq) was added to achieve a solution pH of 11. This mixture was extracted with Et2O (3 x 10 mL). The combined organic layers were washed with H2O (15 mL), brine (15 mL), dried (Na2SO4), filtered and concentrated. The crude mixture was then immediately subjected to flash chromatography (90 % EtOAc/ hexane) to afford 1.02 g (4.4 mmol, 36 %) of the title compound as a white powder. This material was then recrystallized from n-heptane to afford 0.6115 g (2.7 mmol, 22 %) of SB-I1-61 was white needles, mp 72 0C (?-heptane); IR (thin film) v = 2969, 1635, 1506, 1439 1H NMR (300 MHz, CDCl3) delta = 8.42 (d, J= 6.8 Hz, IH), 8.09 (d, J= 9.0 Hz, IH), 7.33-7.27 (m, IH), 6.82 (ddd, J= 6.8, 6.8, 1.2 Hz, IH), 3.75 (sept, J = 6.9 Hz, IH), 2.47-2.39 (m, IH), 1.40 (d, J= 6.9 Hz, 6H), 1.27-1.17 (m, 2H), 0.99-0.93 (m, 2H); 13C NMR (150 MHz, CDCl3) delta = 194.8, 163.1, 141.6, 128.9, 127.4, 118.9, 113.2, 110.7, 27.8, 22.4, 20.4, 10.2; MS (EI) m/z 229 (M+ 1, 18.2), 228 (M+, 100.0), 213 (46.4), 200 (13.1), 199 (23.4), 198 (14.1), 185 (23.2), 171 (23.2), 160 (13.5), 145 (11.8), 132 (10.2), 131 (13.8), 119 (11.6), 117 (18.0), 92 (10.2 ), 91 (10.9), 90 11.0), 84 (11.2), 78 (17.6), 69 (24.6) 51 (10.9); HRMS (EI) calcd for C14H16N2O: 228.1263, found: 228.1261; Anal. Calcd for Ci4H16N2O: C, 73.66 %; H, 7.06 %; Found: C, 73.93 %; H, 7.25%. Compound 1046.

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Reference:
Patent; AVIGEN, INC.; WO2007/146087; (2007); A2;,
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2318-25-4, Name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 2318-25-4, 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.

.To a mixture of 281 g of Compound (I-4) suspended in 1.6 liters of acetonitrile, 210 ml of triethylamine was added while stirring at a room temperature. Following stirring for 30 minutes, 318 g of the foregoing Intermediate (I-3) and 36 ml of acetic acid were added in this order to react them. After reacting for 10 hours, 3 liters of water was added and stirring was continued. Precipitated crystals were collected by filtration. The crystals were washed with water and dried. As a result, 324 g (yield 71percent) of the objective Intermediate (I-5) was obtained, as a white crystal.

Statistics shows that Ethyl 3-ethoxy-3-iminopropionate hydrochloride is playing an increasingly important role. we look forward to future research findings about 2318-25-4.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US6649771; (2003); B2;,
Ester – Wikipedia,
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35180-01-9,Some common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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 stirred suspension of PMPA (7.26 g, 0.026 mmol) in DMF (100 mL) was added Et 3 N (10.8 mL, 0.0778 mmol) at 50 C. The reaction mixture became homogeneous and chloromethyl isopropyl carbonate (12.1 g, 0.0778 mmol) was added to the reaction mixture and stirring was continued at 50 C. (oil bath temperature) for 20 h. The solvent was removed under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 10% isopropanol in CH 2 Cl 2 removed all nonpolar impurities. Further elution with the same solvent mixture yielded 1.3 g (about 10%) of the prodrug.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35180-01-9, its application will become more common.

Reference:
Patent; GILEAD SCIENCES INCORPORATED; ARIMILLI, MURTY N; CUNDY, KENNETH C; DOUGHERTY, JOSEPH P; KIM, CHOUNG U; OLIYAI, REZA; STELLA, VALENTINO J; (59 pag.)JP2015/164934; (2015); A;,
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1559-02-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1559-02-0 as follows.

To a solution of diethyl cyclopropane-1,1-dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight. The ethanol was removed under reduced pressure. The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mL*3). The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4 %). 1H NMR (400MHz, CDCl3): delta 1.27 (t, J=6.7Hz, 3H), 1.83 (m, 2H), 1.86 (m, 2H), 4.25 (m, 2H).

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Xi, Ning; XI, Ning; (152 pag.)EP2408300; (2016); B1;,
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