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.

Methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate Methyl 7-amino-heptanoate hydrochloride (7.0 g, 35.9 mmol) was dissolved in dichloromethane (75.4 mL), and N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide (10.0 g, 38.6 mmol) and triethylamine (10 mL, 71.7 mmol) were then added at room temperature. The mixture was stirred for 5 hours, and then quenched with water (100 mL), and separated. The aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 8.89 g (29.3 mmol, 82% yield) of methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate. 1H-NMR (CDCl3) delta: 0.04 (9H, s), 0.97 (2H, br.t, J = 8.4 Hz), 1.20-1.76 (8H, m), 2.31 (2H, t, J = 7.4 Hz), 3.07-3.23 (2H, m), 3.67 (3H, s), 4.14 (2H, br.t, J = 8.4 Hz), 4.50-4.70 (1H, m)

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; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); A1;,
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Application of 15441-07-3, These common heterocyclic compound, 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, 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 solution of Compound IE (40 mg, 0.092 mmol) and triethylamine (0.026 mL, 0.184 mmol) in CH2CI2 (1 mL) in an ice bath was added methyl 3- (chlorosulfonyl)propanoate (25.7 mg, 0.138 mmol). Upon completion of addition, the reaction mixture was stirred in the ice bath for 15 min. After this time, the reaction mixture was allowed to warm to rt, where it stirred for 3 h. At the conclusion of this period, the reaction mixture was quenched with saturated aq aHCOs (1 mL) and then extracted with CH2CI2 (3 x 2 mL). The combined organic layers were dried( a2S04), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, CELC^-EtOAc gradient 0 to 90% EtOAc) to afford Example 2 as a white solid (42 mg, 78% yield). XH NMR (500 MHz, DMSO- d6) delta ppm 8.24 (2H, s), 7.98 (IH, d, J=1.9 Hz), 7.64 (IH, d, J=8.5 Hz), 7.51 (IH, dd, J=8.5, 1.9 Hz), 6.20 – 6.26 (IH, m), 5.36 – 5.44 (IH, m), 4.15 – 4.23 (2H, m), 3.91 – 3.95 (2H, m), 3.62 (3H, s), 3.51 – 3.59 (2H, m), 3.46 (2H, t, J=5.6 Hz), 3.40 (2H, t, J=7.2 Hz), 2.74 (2H, t, J=7.2 Hz), 2.57 – 2.66 (2H, m), 2.38 (2H, t, J=7.4 Hz), 2.09 – 2.19 (2H, m), 1.70 – 1.81 (2H, m), 1.47 – 1.58 (2H, m), 0.88 (3H, t, J=7.3 Hz).LC/MS (m/z) = 586 (M+H)+.

The synthetic route of 15441-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
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Reference of 5941-55-9, The chemical industry reduces the impact on the environment during synthesis 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, I believe this compound will play a more active role in future production and life.

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (10.00 g, 92.51 mmol) in DMF (350.00mL) was added ethyl (E)-3-ethoxyacrylate (13.34 g, 92.51 mmol) and Cs2CO3 (60.38 g, 185.02mmol). The mixture was stirred at 100C for 2 hrs. After LCMS showed the reaction was complete, the reaction mixture was cooled to 25C, then added to water (300 mL), acidified by HC1 (1 M) till pH = 4, then filtered. The filter cake was dried in vacuum to give 5-hydroxypyrazolo[1,5- ajpyrimidine-3-carbonitrile (10.00 g, yield: 67.5 1%) as a white solid.

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, Ethyl (E)-3-Ethoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
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13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, 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. Application In Synthesis of Methyl 3-(methylamino)but-2-enoate

General procedure: 1195 mg (9.25 mmol 1 eq.) 1 and 1000 mg (9.25 mmol 1 eq.) 1,4-benzoquinone is solved in 12 mL nitromethane. The mixture is left for 24 hrs (no stirring). Crystals of product precipitate. They were filtered, washed with nitromethane and recrystallized from EtOAc. Rf in PE+EtOAc 2+1: 0.2. Yellow solid, yield: 1300 mg, 64 %. Compound described in 2.

The synthetic route of 13412-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Schaefer, Anja; Burstein, Ethan S.; Olsson, Roger; Bioorganic and Medicinal Chemistry Letters; vol. 24; 8; (2014); p. 1944 – 1947;,
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10602-03-6, name is Ethyl 4-ethynylbenzoate, 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. Recommanded Product: 10602-03-6

General procedure: To a solution of 10S1 (0.10 g, 0.59 mmol), Pd(PPh3)4 (41 mg, 0.035 mmol), and CuI (34 mg,0.18 mmol) in degassed tetrahydrofuran/diisopropylamine (THF/DIPA) (5/1, v/v) (19 mL) was added2,5-diiodothiophene (DIT) (0.20 g, 0.59 mmol). The solution was stirred at 60 C for 5 h. After coolingto room temperature, the reaction mixture was diluted with dichloromethane and passed through Celiteto remove the metal catalyst. The solution was washed with 1 N HCl aqueous solution and water, andthen dried over Na2SO4. After removing the solvent by evaporation, the crude product was purified bysilica gel chromatography using hexane-dichloromethane (3/2, v/v) as the eluent to give the desiredproduct as a pale yellow solid (62 mg, 27% yield).

The synthetic route of 10602-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ikai, Tomoyuki; Shimizu, Sho; Kudo, Tomoya; Maeda, Katsuhiro; Kanoh, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 90; 8; (2017); p. 910 – 918;,
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Electric Literature of 91367-05-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 91367-05-4 name is Methyl 4-chloro-3-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

17.0 mL glacial acetic acid, 16.5 mL acetic anhydride and 2.5 mL H2SO4 were cooled in ice bath. Then X13 1.84 g (0.01 mol) and Cr2O3 3 g (0.03 mol) were added in small portion. The mixture was reacted in ice bath for 3 h. The reaction solution was poured into 200.0 mL ice water and stirred vigorously for 30 min. The resulting precipitates were collected by filtration and washed with water (70.0 mL x 3) to afford gray solid which was added into 50.0 mL eggplant flask. 16.0 mL CH3OH, 16.0 mL water and 0.4 mL H2SO4 were added to and refluxed for 30 min. The residue was added into water,and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate extracts were washed with water (80 mL) and brine (80 mL) respectively, and then dried with anhydrous Na2SO4. When the solvent was evaporated, the yield of yellow solid compound X14 was 1.35 g (68.2 %). mp: 131-133 C. 1H NMR (300 MHz, DMSO-d6): delta 3.90 (s, 3H, OCH3), 7.79 (d, 1H, Ar-H, J = 8.4 Hz), 8.18 (d, 1H, Ar-H, J = 8.4 Hz), 8.35 (s, 1H, Ar-H), 10.34 (s, 1H, CHO). IR (KBr): 3425, 3082, 3003, 2953, 1726, 1720, 1689, 1188, 983, 759 cm-1. MS [M+H]+: 199.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-chloro-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Jiao, Yu; Xin, Bo-Tao; Zhang, Yanmin; Wu, Jianbing; Lu, Xiaolin; Zheng, Ying; Tang, Weifang; Zhou, Xiang; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 170 – 183;,
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Electric Literature of 18595-14-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 18595-14-7 name is Methyl 4-amino-3-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Under a nitrogen atmosphere, to a 100-mL four-necked flask were added 5-methylmenthyl carboxylic acid (rac-11a) (600 mg, 3.03 mmol) obtained in Synthesis Example 7, 8, 9, or 19, thionyl chloride (0.33 mL, 1.50 eq.), and a catalytic amount of DMF, followed by stirring at room temperature for 3 hours. The solution in the system was distilled off under reduced pressure, and toluene (2 mL) was added thereto. The inside of the system was cooled to 10 C. or lower in an ice bath, and 3-methyl-4-aminobenzoic acid methyl ester (1.50 g, 3.0 eq.) was added slowly thereto. After two and a half hours, completion of the reaction was confirmed by GC-MS, and a post-treatment was performed. The reaction solution was transferred to a separating funnel, and tap water and chloroform were added thereto to effect washing. The oil layer was washed twice with dilute hydrochloric acid, and further washed once with a saturated saline solution, and then dried with anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and then isolation and purification were performed by column chromatography (heptane/ethyl acetate=4/1), whereby an amorphous solid was obtained (306 mg, yield: 29%). HRMS: mass: 345.2304 actual measurement value: 345.2298 1H-NMR (500 MHz, CDCl3): delta0.85-0.98 (m, 12H), 1.20-1.33 (m, 3H), 1.45-1.65 (m, 4H), 1.82 (quid, 1H, J=6.6, 2.1 Hz), 2.29-2.40 (m, 4H), 7.05 (br, 1H), 7.86-7.90 (m, 2H), 8.14 (d, 1H, J=8.2 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; ITOH, Hisanori; HORI, Yoji; OTSUKA, Masashi; MATSUMOTO, Takaji; SATO, Tomoharu; (50 pag.)US2018/57447; (2018); A1;,
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Some common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, molecular formula is C4H5ClF2O2, 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. category: esters-buliding-blocks

TEOF (130 g, 0.88 mol) was placed in a flask equipped with a magnetic stirring bar and a vacuum distillation cooler. ECDFAA (35 g, 0.175 mol) was added. The resulting mixture was heated to 110C (outer temperature of the flask) under a mild vacuum (300 mbar) ; ethanol formed during the reaction is slowly distilled out of the vessel. After 2h, the starting material was completely consumed, and product formation was observed by GC analysis. Excess of TEOF was removed from the reaction mixture by distillation (at 100C, starting with a pressure of 100 mbar at the beginning and 10 mbar at the end, to remove all TEOF traces), resulting pure product as pale yellow liquid with quantitative yield. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.15 (t, 3 H) 1.20 (t, 3 H) 1.27 (t, 3 H) 3.49 – 3.57 (m, 1H) 3.61 – 3.69 (m, 1H) 3.71 – 3.79 (m, 2 H) 4.23 (q, 2 H) 4.34 (d, J=8.24 Hz, 1 H) 5.18 (d, J=8.24 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 383-62-0, its application will become more common.

Reference:
Patent; SOLVAY SA; Januzems, Janis; EP2644598; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 70347-04-5, 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. 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-methoxy-3-methylbenzoate (16 g) was dissolved in EtOAc (100 mL) and then N- bromosuccinimide (18.96 g) and 2,2′-azobisisobutyronitrile (1 g) were added. The mixture was then heated to 800C for 4 h. After cooling to r.t. sat. sodium thiosulfate solution was added, the organic phase was separated, washed with brine, dried and the solvents removed by evaporation. The crude product was dissolved in mixture of isohexane-EtOAc (9:1) and a solid was produced which was collected to give the subtitle compound (11.82 g); 1H NMR (CDCl3): 8.05-7.98 (m, 2H), 6.91 (d, IH), 4.55 (s, 2H), 3.96 (s, 3H), 3.89 (s, 3H). LC-MS m/z 260.

The synthetic route of Methyl 4-methoxy-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; DAINIPPON SUMITOMO PHARMA CO., LTD; ASTRAZENECA UK LIMITED; BENNETT, Nicholas, James; MCINALLY, Thomas; THOM, Stephen; WO2010/133885; (2010); 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. 87-24-1, name is Ethyl 2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H12O2

Example 1 Preparation of intermediate A: Ethyl 2-methylbenzoate (15.0 g, 91 mmol) in ethyl acetate (400 mL) was treated with N-bromosuccinimide (19.5 g, 110 mmol). The resulting solution was illuminated with a 65 W mercury-halogen lamp for 16 h, which provided enough heat to bring the solution to a gentle reflux. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added (100 mL each). After separation of the organic layer, the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic extracts were washed twice with water (100 mL each) and then with brine (100 mL), and then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product so obtained was purified by flash chromatography (ethyl acetate/hexane) to afford A as a yellow oil (21.3 g).

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 87-24-1.

Reference:
Patent; Roche Palo Alto LLC; US2010/16312; (2010); A1;,
Ester – Wikipedia,
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