Author: Jessica.F

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 31603-77-7 as follows. category: nitriles-buliding-blocks

EXAMPLE 53 (6-Biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 4-biphenylaceto-nitrile (263 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carboxaldehyde (300 mg, 1.24 mmol) was added and the reaction heated at 110 C. for 1 hour, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluding with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 427 mg (83%) of (6-biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 245-249 C. Mass spectrum (CI) 418 (M+). Analysis calculated for C27 H23 N5: C, 77.67; H, 5.55; N, 16.78. Found: C, 76.16; H, 5.54; N, 16.36.

According to the analysis of related databases, 31603-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US5945422; (1999); A;,
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Reference of 55984-93-5, 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. 55984-93-5, name is 2-Methylterephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methylterephthalonitrile (1.42 g, 1.0 mmol) and t-butoxybis(dimethylamine)methane (3.5 g, 2.0 mmol) were heated with 15 mL of DML at 75 ¡ãC for 12 h under N2. The DMF was removed and hexane was added. The precipitate formed was filtered and dried to give 1.85 g of the desired product. MS: 504.4, (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, 2-Methylterephthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123050; (2005); A2;,
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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. 13989-82-7, name is 4-(Dimethylamino)butanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Dimethylamino)butanenitrile

To a suspension of lithium aluminum hydride (LAH) (4.74 g, 120.90 mmol) in dry ether (100 ml) was added dropwise a solution of N-(3-cyanopropyl)-N,N-dimethylamine 321 (4.10 g, 36.61 mmol) in dry ether (50 ml) at 0 C. After complete addition, the reaction mixture was stirred for two hours while allowing the temperature to raise from 0 C. to room temperature. The reaction mixture was quenched with 2N NaOH at 0 C. and the resulting white suspension was filtered through Celite and washed with ether. The ether filtrate was dried over K2 CO3, filtered and concentrated in vacuo, yielding N,N-dimethyl-1,4-diaminobutane 322 as a colorless oil (2.5 g, 60% yield). 1 H NMR (400 MHz, CDCl3) delta: 1.43 (4H, m, –CH2 –CH2 –CH2 –CH2 –), 1.93 (2H, br s, –NH2), 2.16 (6H, s, –N(CH3)2), 2.21 (2H, t, –CH2 CH2 N), 2.66 (2H, t, –CH2 CH2 NH2).

According to the analysis of related databases, 13989-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Magainin Pharmaceuticals, Inc.; US5637691; (1997); A;,
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51655-39-1, name is 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile, 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. Quality Control of 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile

Example 7 3-(ETHOXY-HYDROXY-METHYLENE)-5,6-DIMETHOXY-3H-INDENE-1-CARBONITRILE, SODIUM SALT A solution of tricyclohexylphosphine (82.0 mg, 0.293 mmol) in ethylene glycol dimethyl ether (10 mL) under nitrogen was charged with palladium (II) acetate (43.7 mg, 0.195 mmol). The reaction was stirred at room temperature until the solution was homogeneous (approx. 15 minutes) and stirred an additional 5 minutes before cooling to 0 C. and charging with sodium tert-butoxide (996 mg, 9.75 mmol). After 5 minutes a solution of 2-bromo-4,5-dimethoxyphenylacetonitrile (1.00 g, 3.90 mmol) and ethyl-3-ethoxyacrylate (0.564 ml, 3.90 mmol) in ethylene glycol dimethyl ether (5 ml) was added dropwise over 10 minutes. Upon complete addition the reaction mixture was warmed to room temperature and then heated to 85 C. for 16 hours. The reaction was cooled to room temperature then diluted with methyl tert-butyl ether (50 mL) and poured into aqueous potassium dihydrogenphosphate (0.25 M, 100 mL). The aqueous layer was separated and solid sodium chloride was added to the aqueous layer until saturated. The aqueous layer was extracted with ethyl acetate (1*125 mL) and this organic layer was washed with aqueous saturated sodium chloride 12*35 ml), dried over sodium sulfate, filtered and concentrated in vacuo affording 3-(ethoxy-hydroxy-methylene)-5,6-dimethoxy-3H-indene-1-carbonitrile, sodium salt, as a dark brown oil (906 mg, 3.3 mmol, 85 %) which crystallized on standing. 1H NMR (400 MHz, d4-MeOH) delta7.64 (s, 1H), 7.46 (s, 1H), 6.99 (s, 1H), 4.56 (q, 2H, J=7.1), 3.86 (s, 6H), 1.38 (t, 3H, J=7.05); 13C NMR (100 MHz,d4-MeOH) delta167.8, 145.0, 144.5, 130.2, 129.4, 126.4, 123.3, 112.5, 104.0, 102.6, 100.7, 79.0, 58.4, 55.6, 14.1; IR (ATR, neat) 3499, 2164, 1629, 1482, 1449, 1282, 1207, 1157, 1124, 1076, 845, 769 cm-1.

The synthetic route of 51655-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singer, Robert A.; US2003/60624; (2003); A1;,
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Reference of 2112-22-3,Some common heterocyclic compound, 2112-22-3, name is 2,3-Dichloro-6-nitrobenzonitrile, molecular formula is C7H2Cl2N2O2, 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.

2,3-dichloro-6-nitrobenzonitrile, 500 gm, was dissolved in 7500 ml of THF in a clean dry RB flask maintaining a nitrogen blanket. 139.3 am of sodium borohydride was added at 25-30 C. The suspension was cooled to 15-20 C. 653 gms of Borontrifluoride etherate was added to the reaction mixture over a period of about 2 hours while maintaining the temperature between 15-30 C. After the addition was complete, the temperature was raised about 65 C. and maintained at reflux for 2 hours. The reaction mixture was cooled to about 0-5 C. A mixture of 2.0 liter water and 200 ml concentrated HCl was slowly added to the reaction mixture while maintaining the temperature below 20 C. After the addition was complete, THF was distilled from the reaction mixture under vacuum maintaining temperature below 50 C. The reaction mixture was cooled to about 10-15 C. and 2.0 liter ethylacetate was added. The pH of reaction mixture was adjusted to 10-11 using 25% aqueous sodium hydroxide solution while maintaining the temperature below 15 C. The ethylacetate layer was separated and concentrated to about half the original volume. The reaction mixture was cooled to 15-20 C. and 500 ml IPA-HC1 was added slowly, maintaining temperature below 30 C. After cooling to about 0-5 C., the solids obtained were filtered and washed with 500 ml chilled ethylacetate. The solids were dried to obtain 2,3-dichloro-6-nitrobenzyl amine hydrochloride (450 gms),

The synthetic route of 2112-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2010/305318; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 590-17-0, name is 2-Bromoacetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 590-17-0, category: nitriles-buliding-blocks

Screening of A3a in existing CWR protocols – standard room temperature conditions: Scheme A52. Screening of A3a in RT-CWR conditions.Benzaldehyde (100 iL, 1.0 mmol, 1.0 equiv.), bromoacetonitrile (86 iL, 1.3 mmol, 1.3 equiv.), phenylsilane (172 iL, 1.3 mmol, 1.3 equiv.) and DIPEA (244 pL, 1.4 mmol, 1.4 equiv.) were reacted using A3a (23 mg, 0.1 mmol, 10 mol %) and 4-nitrobenzoic acid (17 mg, 0.1 mmol, 10 mol %) in ethyl acetate (0.33 mL) at RTfor24 h (Scheme S2). The crude product was analyzed by 1H NMR spectroscopy, which showed 100%conversion to product and an E/Z ratio of 93:7.The crude product was purified via flash column chromatography to afford pure product as a colorless oil (126 mg, 98%, E/Z93:7).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DUBLIN CITY UNIVERSITY; O’BRIEN, Christopher; WO2014/140353; (2014); A1;,
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Reference of 72635-78-0,Some common heterocyclic compound, 72635-78-0, name is 3-Amino-4-bromobenzonitrile, molecular formula is C7H5BrN2, 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 following intermediates as shown in Table 48 are synthesized in a similar fashion from the appropriate intermediatesStep 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-bromobenzonitrile, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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Related Products of 331-62-4, 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 331-62-4 as follows.

BBr3 (20 mL, 0.211 mol) was added to 3-fluoro-4-methoxybenzonitrile (15.6 g, 0.103 mol) in dichloromethane (100 mL) at 0 ¡ãC. The mixture was refluxed for 3 days under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure gave 13.3 g (94percent) of the product as a gray solid. :H NMR (400 MHz, CDC13) delta 7.38-7.42 (m, 2H), 7.09 (dd, J= 8.8 Hz, 8.4 Hz, 1H), 5.68 (s, 1H).

According to the analysis of related databases, 331-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Li; HU, Yuandong; YU, Rong; HU, Wei; ZHAO, Na; PENG, Yong; LUO, Hong; HAN, Yongxin; WO2013/97773; (2013); A1;,
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These common heterocyclic compound, 13989-82-7, name is 4-(Dimethylamino)butanenitrile, 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. SDS of cas: 13989-82-7

4-(Dimethylamino)butyronitrile (4.4 g) was dissolved in tetrahydrofuran (40 mL), and a 1 mol/L borane/tetrahydrofuran solution (40 mL) was added dropwise under ice-cooling. After the completion of the reaction, water was added to the reaction solution. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography. A hexane:ethyl acetate=1:1 effluent fraction was concentrated to give (4-(dimethylamino)butyronitrile-N1)trihydroboron (2.8 g). The reaction was carried out in the same manner as in Example 82 using N,N-dimethyl-2,3-dimethylbenzamide (3.9 g) and (4-(dimethylamino)butyronitrile-N1)trihydroboron to give (3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g). (3-(3-(Dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g) was dissolved in acetone (20 mL), and conc. hydrochloric acid (1 mL) was added at room temperature. After the completion of the reaction, the solvent was concentrated. Toluene was added to the obtained residue, and the mixture was extracted with water. Potassium carbonate was added to basify the aqueous layer, and the mixture was extracted with chloroform and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography (NH silica gel, Fuji Silysia Chemical Ltd.). A chloroform effluent fraction was concentrated, and diisopropyl ether was added to the obtained residue. The precipitated crystals were collected by filtration to give 3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one (1.5 g). melting point: 105-106C.1H-NMR(CDCl3) delta: 1.79-1.89(2H,m), 2.34(6H,s), 2.39(2H,t,J=6Hz), 2.49(3H,s), 2.69(2H,t,J=6Hz), 6.34(1H,s), 7.31(1H,t,J=8Hz), 7.42(1H,dd,J=1Hz,7Hz), 8.23(1H,d,J=8Hz), 11.37(1H,brs).

The synthetic route of 4-(Dimethylamino)butanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1396488; (2004); A1;,
Nitrile – Wikipedia,
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Electric Literature of 76574-39-5, 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. 76574-39-5, name is 2-(2-Bromo-6-chlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(2-Bromo-.6-chlorophenyl)acetonitrile (450 mg, 2.0 mmol) (43-1), 3- pyridylboronic acid (251 mg, 2.1 mmol) (43-2), potassium fluoride (230 mg, 3.9 inmol), 1,4- dioxane (12 mL), methanol (3.6 rnL), Pd2(dba)3 (71 rng, 0.080 mrnol) and dicyciohexyl-12-(2,6- dimethoxyphenyl)phenyi]phosphane (32 Ing, 0.080 mmol) were combined under an atmosphere of nitrogen and the resulting mixture was heated at 80 C After 16 h, the reaction was filtered and concentrated under reduced pressure. The resulting oil was dissolved in DCM and purified by silica gel chromatography eluting with methanol/dichloromethane to afford 317 mg (71%) 2- [2.-chloro-6-(-pyridyl)phenyllacetonitriie (43-3). LCMS (ESI): [M+Hf = 229.1

The synthetic route of 2-(2-Bromo-6-chlorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); A1;,
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