Tag: M.W=0-100

Synthetic Route of 151-18-8, The chemical industry reduces the impact on the environment during synthesis 151-18-8, name is 3-Aminopropanenitrile, I believe this compound will play a more active role in future production and life.

Example 386 N-(3-(((2-cyanoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-6-methylpyridine-2-carboxamide To a solution of 4-(((6-methylpyridin-2-yl)carbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 47 (0.66 g, 2.0 mmol) and 3-aminopropionitrile (0.18 mL, 2.4 mmol) in DMF (15 mL), WSC (0.41 g, 2.4 mmol) and HOBt (0.32 g, 2.4 mmol) were added, and the mixture was stirred at room temperature for 6 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 1:1) to give the title compound (0.75 g, yield 92%) as crystals. melting point 186-187 C. 1H-NMR (CDCl3): delta 1.60-1.80 (3H, m), 2.00-2.15 (2H, m), 2.15-2.30 (1H, m), 2.70 (3H, s), 2.76 (2H, t, J=6.6 Hz), 3.75 (2H, t, J=6.6 Hz), 3.65-3.80 (1H, m), 4.00-4.55 (1H, m), 5.36 (1H, d, J=7.2 Hz), 7.20-7.30 (1H, m), 7.32 (1H, d, J=7.2 Hz), 7.75 (1H, t, J=7.7 Hz), 8.03 (1H, d, J=6.9 Hz), 8.58 (1H, s), 11.53 (1H, s).

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, 3-Aminopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
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Reference of 107-91-5, 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. 107-91-5 name is 2-Cyanoacetamide, 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.

Pentadione (10 g, 0.1 mol), cyanoacetamide (8.4 g, 0.1 mol) and sodium hydroxide (4 g, 0.1 mol) were added to anhydrous ethanol and stirred overnight at room temperature. The reaction was monitored by TLC and the reaction was stopped. The precipitated solid material was filtered off with suction, washed with a little water, ethanol and diethyl ether and dried to give 4,6-dimethyl-3-cyanopyridone, 142 g, 95.8%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Cyanoacetamide, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan University; Puluo Pharmaceutical Co., Ltd.; Yu Luoting; Wei Yuquan; (24 pag.)CN107573327; (2018); A;,
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Related Products of 4426-11-3,Some common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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 mixture of cyclobutanecarbonitrile (0.70 g, 8.6 mmol) and 2-chloro-6-fluorobenzoic acid (0.5 g, 2.9 mmol) in THF (9.6 mL) at 0 C.Was added KHMDS (0.5 M in toluene, 12.6 mL, 6.3 mmol). The resulting mixture was heated at 70 C. for 3 h, then cooled and concentrated in vacuo. The residue was taken up in 20 mL H 2 O and extracted three times with Et 2 O. The aqueous layer was acidified with 2 N HCl and extracted with CHCl 3 / i-PrOH (3: 1). The combined organic portion was dried over Na 2 SO 4 and concentrated. This crude residue was used directly.

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

Reference:
Patent; Mrck Sharp and Dohme Corp; Blair T, Lapointe; Peter H, Fuller; Hakan, Gunaydin; Kun, Liu; Daneille F, Molinari; Qinglin, Pu; Mark E, Scott; B Wesely, Trotter; Hongjun, Zhang; (117 pag.)JP2018/531957; (2018); A;,
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Electric Literature of 2469-99-0, 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. 2469-99-0, name is 3-Oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of (4-fluorophenyl)hydrazine (HCl salt, 802 mg, 5.8 mmol) and 3-oxo-butyronitrile (500 mg, 5.8 mmol) in EtOHIAcOH (10 mL/0.2 mL) was stirred at refluxing overnight. The reaction solution was concentrated in vacuum to give crode 2-(4-fluorophenyl)-5-methyl-2H-pyrazol-3-ylamine (1.1 g, yield:quantitative) as a yellow solid which was used for the next step without any purification. ?H NMR (400 MHz,DMSO-d6): = 7.6-7.64 (m, 2H), 7.45 (t, J= 8.8 Hz, 1H), 5.66 (s, 1H), 2.24 (s, 3H).

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

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, belongs to nitriles-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: 15760-35-7

3 -oxocyclobutanecarbonitrile [1266] A mixture of 3-methylenecyclobutanecarbonitrile (9.39 g, 101 mmol), dichloromethane (200 mL), water (300 mL), acetonitrile (200 mL), and ruthenium(III) chloride hydrate (0.500 g, 2.218 mmol) was cooled to <5 C, followed by portionwise addition of sodium periodate (88 g, 413 mmol) at <20 C, and stirred for 10 minutes. The mixture was diluted with dichloromethane and partitioned. The organic phase was filtered through a silica pad, dried ( a2S04), filtered, concentrated, and passed through a silica plug again, eluting with 200 mL dichloromethane to provide Example 125A (8.21 g, 86 mmol, 86 % yield) as a white solid. XH NMR (300 MHz, CDC13) ? 3.60 - 3.22 (m, 5H). The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
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Related Products of 630-18-2,Some common heterocyclic compound, 630-18-2, name is Pivalonitrile, molecular formula is C5H9N, 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.

The catalytic activity of 5 mol % [RuCl2(PTA)4] toward nitrile hydration was evaluated in aqueous solution at 100 C. with 1 mmol nitrile in a culture tube under air (Scheme 2). Under the conditions described here, RuCl3 (5 mol %) provided a 54% conversion of benzonitrile to benzamide in 24 hours. Benzonitrile hydration by 2 mol % RuCl3 was previously reported to yield 28% benzamide after 3 h at 130 C. No hydration was observed in the absence of a catalyst, or with PTA, [RuCl2(eta6-toluene)]2, or [RuCl2(PPh3)3] as catalysts. Benzonitrile hydration by [RuCl2(PTA)4] did not occur at 50 C. and provided only 23% conversion after 24 h at 75 C. The hydration of benzonitrile catalyzed by [RuCl2(PTA)4] showed a >99% conversion to benzamide at 100 C. after 7 hours, in contrast to the inactive [RuCl2(PPh3)3], potentially demonstrating a cooperative effect of the nitrogen-containing PTA versus PPh3. For comparison, nitrile hydration catalyzed by 5 mol % [RuCl2(eta6-arene)(PTA)] (eta6-arene=benzene, p-cymene, 1,3,5-trimethylbenzene, and hexamethylbenzene), showed >98% conversions in 4-9 h for aqueous benzonitrile hydration under N2 at 100 C. An in situ generated catalyst formed by the addition of RuCl3 hydrate with 6 equivalence of PTA provided results similar to the preformed complex RuCl2PTA4 (Table 1).The conversion of various nitriles (1a-1n) to the corresponding amides (2a-2n) was explored with results summarized in Table 1. All nitriles were efficiently converted to amides with 67-99% conversion in 7 hours and >99% conversions by 24 hours, with the exception of 2-cyanopyridine (1j, 81% after 24 h). After completion, the reaction was cooled to 0 C. and, in most cases, the product amides crystallized out as white needles and were easily isolated in 67-81% yield by decantation. Identity of the isolated amides (2a-2n) was confirmed by GC-MS and NMR spectroscopy. Substituted benzonitriles bearing electron-withdrawing groups (Table 1 above, entries 1g-1i) exhibited slightly more efficient conversions to amides than those with electron-donating groups (entries 1b-1f). Presumably, the presence of the electron-withdrawing group makes the nitrile carbon more susceptible to nucleophilic attack by an activated water molecule. As previously reported for ortho-substituted benzonitriles, o-tolunitrile exhibited lower conversion relative to m- and p-tolunitriles (Table 1, entries 1b-1d), which is attributed to steric hindrance of the o-tolunitriles. Hydration of 4-cyanobenzaldehyde led to 4-formylbenzamide in a 99% conversion in 7 h with an intact formyl moiety (entry 1i). The coordinating ability of the pyridyl functionality reduced catalytic activity as hydration of 2-cyanopyridine to picolinamide resulted in only 81% conversion after 24 h (entry 1j).[RuCl2(PTA)4] was also effective as a hydration catalyst for the less reactive aliphatic nitriles (Table 1, entries 1k-1m). 4-Methylbenzyl cyanide was transformed with 99% conversion in 7 hours (entry 1k) into the amide. Hydration of the sterically bulky pivalonitrile (1m) to pivalamide proceeded with a 99% conversion in 24 h although a modest conversion of 67% was observed after 7 h (entry 1m). The resistance of tertiary nitriles toward hydrolysis has been noted. The industrially important acrylonitrile was almost quantitatively converted into acrylamide in 7 hours without observation of polymerization or hydrolysis byproducts (Table 1, entry 1n). For all the nitrile hydrations studied, the corresponding amides were the only product observed (no carboxylic acids were detected by GC-MS). Thus, the catalytic conditions described here are compatible with ether (entry 1e), hydroxyl (entry 10, nitro (entry 1g), bromo (entry 1h), formyl (entry 1i), pyridyl (entry 1j), benzyl (entry 1k), alkyl (entries 1l-1m), and olefinic (entry 1n) functional groups, which establishes a wide synthetic scope.

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

Reference:
Patent; Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada; Frost, Brian J.; Lee, Wei-Chih; US2013/96344; (2013); A1;,
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Application of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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: First of all, a mixture of 3-oxoalkanonitrile (1 mmol) and hydrazine hydrate (55% aq) (2 mmol) was magnetically stirred in ethanol (5 ml) for 2h under room temperature condition. After completion of the reactions, which was followed by TLC EtOAc:n-hexane 3:1, 2-phthaldehydic acid (1 mmol), CH-acid (1 mmol), and 4-toluenesulfonic acid (0.3mmol) as catalyst were added. Then, the mixture magnetically stirred for 22 h under reflux condition. Reaction solvent was removed by vacuum and participate was washed with methanol. Finally, the residue was purified by recrystallization in mixture of DMSO/methanol (5:2).

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alizadeh-Kouzehrash, Meysam; Rahmati, Abbas; Tetrahedron; vol. 76; 7; (2020);,
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Reference of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1 -[4-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile[194] 2-Fluoro-4-(trifluoromethyl)pyridine (0.731 mL, 6 mmol) and cyclobutane- carbonitrile (0.841 mL, 9.00 mmol) were dissolved in toluene (10 mL). 0.5M KHMDS (18.00 mL, 9.00 mmol) in toluene was added, and the reaction stirred at ambient temperature for 3 days. The reaction mixture was quenched with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgS04, filtered, and concentrated. The residue was chromatographed on an AnaLogix SF25-60g column and eluted with 10% EtOAc in hexanes to give Example 116A (0.88 g, 3.89 mmol, 64.8% yield). MS (DCI+): m/z 227.2 (M+H), 244.1 (M+NH4). XH NMR (300 MHz, DMSO-d6) ? 8.93 (d, J= 5.0 Hz, 1H), 7.96 – 7.90 (m, 1H), 7.82 (ddd, J= 5.1, 1.5, 0.7 Hz, 1H), 2.90 – 2.68 (m, 4H), 2.35 – 2.21 (m, 1H), 2.13 – 2.00 (m, 1H).

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

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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Reference of 151-18-8,Some common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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 DMF (1.6 mL) solution of 3-(2-[[3-(trifluoromethyl)phenyl]amino][1,2,4]triazolo[1,5-a]pyridin-8-yl)benzoic acid (80 mg, 0.201 mmol) obtained in Reference Example 122, 3-aminopropanenitrile (0.016 mL, 0.221 mmol), HATU (91.6 mg, 0.241 mmol), and N,N-diisopropylethylamine (0.042 mL, 0.241 mmol) was stirred for 3 hours at room temperature. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off at reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from hexane and ethyl acetate to give 68.4 mg of the titled compound (yield 76%) in solid form. Melting point: 214-215 C.1H-NMR (DMSO-d6) delta: 2.81 (2H, t, J=6.5 Hz), 3.55 (2H, q, J=6.5 Hz), 7.15-7.26 (2H, m), 7.53 (1H, t, J=8.0 Hz), 7.65 (1H, t, J=8.0 Hz), 7.89-7.97 (3H, m), 8.21 (1H, br s), 8.34-8.41 (1H, m), 8.49 (1H, t, J=1.6 Hz), 8.89 (1H, dd, J=6.7, 1.0 Hz), 8.99 (1H, t, J=5.7 Hz), 10.22 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Aminopropanenitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2010/41891; (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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H5NO

General procedure: 3-Acetyl-2-aminothiophene Derivatives; General Procedure Carbonyl compound (0.025 mol) was added to freshly prepared cya-noacetone (0.03 mol) in either MeOH or EtOH (40 mL). Sublimed sul-fur S8 (0.03 mol) and piperidine (0.03 mol) were added and the mix-ture was stirred and heated to 55-65 C for 24 h. Ice was then addedand the formed precipitate was filtered under vacuum and washedwith water. The obtained solid was crystallised from a suitable sol-vent, with the exception of 4g and 4j, which were collected directlywithout further purification.

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 2469-99-0.

Reference:
Article; Abdelwahab, Ahmed B.; Hanna, Atef G.; Kirsch, Gilbert; Synthesis; vol. 48; 17; (2016); p. 2881 – 2888;,
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