Tag: M.W=0-100

6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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. Computed Properties of C4H6N2O

Step 3To a 10 ml seal tube was added 5-(7-pivaloyl-5-((2-trimethylsilyl)ethoxy)methyl)-5H- pyrrolo[2,3-b]pyrazin-2-ylamino)thiophene-2-carbaldehyde (0.150 g, 0.000327mole), 2-cyano – N,N- dimefhylacetamide (0.183 g, 0.00163 mole) and ethanol (5 ml) followed by addition of piperidine acetate (3.3 M solution in water) (1.5 ml, 0.00495 mole) at RT. The tube was sealed and the reaction mixture was heated at 80 C for 24 hr. After completion of reaction, ethanol was distilled out, the reaction mixture was diluted with ethyl acetate. The organic layer was separated and washed with water, dried over sodium sulphate and concentrated to give the desired crude product which was purified using column purification by eluting the compound with 35% ethyl acetate in hexane to yield 1 10 mg of 2-cyano-N,N-dimethyl-3-(5-(7-pivaloyl-5-((2- trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)thiophen-2-yl)acrylamide

The synthetic route of 6330-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
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Synthetic Route of 2469-99-0, The chemical industry reduces the impact on the environment during synthesis 2469-99-0, name is 3-Oxobutanenitrile, I believe this compound will play a more active role in future production and life.

Under nitrogen atmosphere, to a 500 mL of round bottom flask were added 2-cyanoacetone (8 g, 0.096mol) and 200 mL of anhydrous ethanol. 2-cyanoacetone was dissolved with stirring at room temperature. Methylhydrazine (4.43 g, 0.096 mol) was added to obtain a resultant mixture. The mixture was slowly warmed and refluxed. After reacting for 3 hr, the solvent was rotary-evaporated to obtain a product as oil. The product was purified by column chromatography to give 4.2 g of the title compound. MS (ESI): m/z 112 (M+H)+

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

Reference:
Patent; Hande Starlake Bioscience Co., Ltd.; Hande Pharma Limited; LI, Chenxi; SHEN, Weisheng; FANG, Yang; LE, Xiaoyong; EP2578587; (2013); A1;,
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Application of 151-18-8, These common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, 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.

(4S)-4-{[(tert-butoxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid (700 mg, 2.52 mmol) was dissolved in DCM. 3-Aminopropanenitrile (228 mI, 3.03 mmol), DMAP (1.23 g, 10.1 mmol) and EDCI (581 mg, 3.03 mmol) was then added and stirred at rt for 18 h. The reaction mixture was diluted with DCM (50 ml.) and washed with 1 M HCI (50 ml.) and sat NaHCO3 (50 ml_). The organic phase was dried with Na2S04, filtered and concentrated to generate methyl (2S)-2-{[(tert- butoxy)carbonyl]amino}-4-[(2-cyanoethyl)carbamoyl]butanoate (762 mg, 91 %). LCMS [M+H]+ m/z 314; 1H NMR (400 MHz, CDCI3) d ppm 6.86 (br. s., 1H), 5.32 (d, J= 7.3 Hz, 1H), 4.23 – 4.38 (m, 1H), 3.76 (s, 3 H), 3.48 – 3.58 (m, 2 H), 2.65 (t, J= 6.5 Hz, 2 H), 2.29 – 2.36 (m, 2 H), 2.15 – 2.25 (m, 1H), 1.84 – 1.97 (m, 1H), 1.45 (s, 9 H).

The synthetic route of 151-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; BENGTSSON, Christoffer; BORHADE, Sanjay; HARALDSSON, Martin; HELLEDAY, Thomas; HENRIKSSON, Martin; HOMAN, Evert; PAULIN, Cynthia; SANDBERG, Lars; SCOBIE, Martin; STENMARK, Pal; VALLIN, Karl; (138 pag.)WO2019/201991; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 4426-11-3, name is Cyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., name: Cyclobutanecarbonitrile

l-[5-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile[187] 2-Fluoro-5-(trifluoromethyl)pyridine (0.603 mL, 5 mmol) and cyclobutane- carbonitrile (0.514 mL, 5.50 mmol) were dissolved in toluene (20 mL). 1M NaHMDS (5.50 mL, 5.50 mmol) in THF 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 SF25-60 g column and eluted with 5% EtOAc in hexanes to give Example 115A (0.36 g, 1.592 mmol, 31.8% yield). MS (DCI+): m/z 244.0 (M+NH4). XH NMR (300 MHz, DMSO-d6) ? 9.09 – 9.02 (m, 1H), 8.33 (dd, J= 8.3, 2.2 Hz, 1H), 7.85 (d, J= 8.3 Hz, 1H), 2.89 – 2.69 (m, 4H), 2.39 – 2.21 (m, 1H), 2.16 – 2.00 (m, 1H).

The synthetic route of 4426-11-3 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; WO2013/62966; (2013); A2;,
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Some common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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. name: 1-(Hydroxymethyl)cyclopropanecarbonitrile

In a 250 mL RBR at 0 C, 1-(hydroxymethyl)cyclopropanecarbonitrile (400 mg, 4.12 mmol) was dissolved in methylene chloride (15 mL) and triethylamine (1.148 mL, 8.24 mmol). Reaction was treated drop wise with methanesulfonyl chloride (0.353 mL, 4.53 mmol) and reaction stirred at 0 C for 2 hr. Reaction was quenched with 20 mL of saturated aqueous Na2C03 solution. Reaction mixture was diluted with Et20 and stirred vigorously for 30 minutes. Organics were isolated, dried (MgS04), filtered and concentrated under reduced pressure providing the title compound as a yellow oil which was used without further purification (622 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98730-77-9, its application will become more common.

Reference:
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; LIN, Xiaodong; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101066; (2012); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33279-01-5, name is 3-Oxopentanenitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Example 5 Preparation of 5-chIoro-2-{r3-ethyl-4-(6-methoxypyridin-3-yI)-l-pyridin-4-yl-lH- pyrazoI-5-yIlaminolbenzoic acid; EPO Step 1. Preparation of 3 -ethyl- 1 -p yridin-4-yl-lH-pyrazol-5-amineTo a 100 mL 3 -neck round-bottom flask fitted with argon inlet, septum and addition funnel was added 4-hydrazinopyridine (7.3 g, 67 mmol), 3-oxo-pentanenitrile (6.5 g, 67 mmol), acetic acid (8.03 g, 133.8 mmol) and ethanol (35 mL). It was heated at reflux overnight. The reaction mixture was cooled to rt and the solvent was evaporated, ethyl acetate (150 mL) was added and the organic layer was washed with sat. NaHCO3 (100 mL), water (100 mL), and brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (20-40% EtOAc/hexane). The product3-ethyl-l-pyridin-4-yl-lH-pyrazol-5~amine was obtained as yellow solid (5.0 g, 40%); 1HNMR (300 MHz, CDCl3) 6 8.50 (d, 2 H), 7.65 (d, 2 H), 5.60 (br s, 2 H), 5.40 (s, 1 H), 2.40(q, 2 H), 1.05 (t, 3 H). LC-MS tn/z 189.1 (MH+), HPLC RT (min) 1.09 {method (A)}.

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:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 151-18-8, name is 3-Aminopropanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 151-18-8

To a suspension of (S)-3-(5-benzylisoxazole-3-carboxamido)-5-methyl-4-oxo- 2,3,4,5-tetrahydrobenzo [b][l,4]oxazepine-7-carboxylic acid (87.0 mg, 0.206 mmol) in DCM (2.0 mL) was added l-chloro-N,N,2-trimethylprop-l -en- 1 -amine (33.1 mg, 0.248 mmol) as a solution in DCM (0.10 ml) dropwise over 1 min. The reaction mixture was stirred at rt for lh and became a homogeneous solution. The reaction mixture was cooled in an ice-bath then 3-aminopropanenitrile (57.9 mg, 0.826 mmol) was added dropwise as a solution in DCM (0.25 mL). The ice-bath was removed then 10 % aq citric acid solution was added and the mixture was stirred vigorously for 15 min . The organic phase was separated, washed with sat. aq sodium bicarbonate and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by FCC( EtO Ac-Hex: 60-80%) to yield the desired product(67.0 mg, 68.5 %). MS (m/z) 474.4 (M+H+).

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:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); 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. 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C5H7NO

In a 250 mL RBR at 0 C, 1-(hydroxymethyl)cyclopropanecarbonitrile (400 mg, 4.12 mmol) was dissolved in methylene chloride (15 mL) and triethylamine (1.148 mL, 8.24 mmol). Reaction was treated drop wise with methanesulfonyl chloride (0.353 mL, 4.53 mmol) and reaction stirred at 0 C for 2 hr. Reaction was quenched with 20 mL of saturated aqueous Na2C03 solution. Reaction mixture was diluted with Et20 and stirred vigorously for 30 minutes. Organics were isolated, dried (MgS04), filtered and concentrated under reduced pressure providing the title compound as a yellow oil which was used without further purification (622 mg).

The synthetic route of 98730-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; LIN, Xiaodong; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101065; (2012); A2;,
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Synthetic Route of 6011-14-9, 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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of Compound (I-1-2) (1.33 g, 3.79 mmol) in dimethylformamide were successively added 2-aminoacetonitrile hydrochloride (0.525 g, 5.68 mmol), HATU (2.159 g, 5.68 mmol) and Et3N (1.049 mL, 7.57 mmol) with ice-cooling, then the reaction mixture was stirred at room temperature for 3 hours. To the reaction solution were added 0.1M hydrochloric acid and ethyl acetate, then the reaction solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound (I-1-3) (1.23 g, 83%) as a yellow solid.Compound (I-1-3); 1H-NMR (CDCl3) delta: 3.97 (s, 2H), 4.24 (d, J=5.6 Hz, 2H), 4.76 (s, 2H), 7.39 (t, J=7.4 Hz, 1H), 7.48 (t, J=7.4 Hz, 2H), 7.63 (d, J=7.1 Hz, 2H), 7.74 (dd, J=8.6, 1.5 Hz, 1H), 8.02-8.07 (m, 3H).

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

Reference:
Patent; Shionogi & Co., Ltd.; US2012/253040; (2012); A1;,
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Electric Literature of 6011-14-9, A common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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.

(a) 4-t-Butoxycarbonylamino-2-methylpyrrole-3-carboxylic acid ethyl ester ; Triethylamine (8.25 mL, 59.17 mmol) was added to a solution of amino acetonitrile hydrochloride (7.00 g, 53.79 mmol) in ethanol (23 mL), and the obtained mixture was then stirred at room temperature for 10 minutes. Thereafter, ethyl acetoacetate (5.47 g, 59.17 mmol) was added to the reaction solution, and the obtained mixture was then stirred at 70C for 1 hour. Thereafter, the solvent was distilled away, and ice water (50 mL) was then added to the reaction solution, followed by stirring at 0C. The generated precipitate was collected by filtration to obtain an enamine compound (7.35 g, yield: 81%) in the form of a colorless powder. The obtained enamine compound (7.35 g, 43.7 mmol) was added to a solution of sodium ethoxide in ethanol prepared from sodium metal (1.11 g, 48.1 mmol), and the obtained mixture was then stirred at room temperature for 18 hours. Thereafter, a 4 M-hydrochloric acid-ethyl acetate solution was added to the reaction solution to neutralize it (pH = 6), and the solvent was then distilled away. The generated precipitate was collected by filtration to obtain an aminopyrrole compound in the form of a brown solid. Triethylamine (4.74 mL, 34.0 mmol), Boc2O (7.42 g, 34.0 mmol), and DMAP (3.12 g, 25.5 mmol) were added to a solution of the obtained aminopyrrole compound in dichloromethane (150 mL). The obtained mixture was stirred at room temperature for 4 hours. Thereafter, water was added to the reaction solution, and it was then extracted with ethyl acetate twice, washed with a saturated saline, and then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the title compound (1.84 g, yield in two steps: 20%) in the form of a colorless oily substance. 1H NMR (400 MHz, CDCl3): delta (ppm) = 8.49 (1H, brs), 7.90 (1H, brs), 7.01 (1H, d, J = 1.9 Hz), 4.31 (2H, q, J = 7.2 Hz), 2.45 (3H, s), 1.49 (9H, s), 1.37 (3H, t, J = 7.2 Hz).

The synthetic route of 6011-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2308838; (2011); A1;,
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