Month: May 2021

51762-67-5, name is 3-Nitrophthalonitrile, 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. category: nitriles-buliding-blocks

4-(methylthio)phenol (0.809 g, 5.78 mmol) was dissolved in10 cm3 dry DMF and thenfinely dried K2CO3 (~2.00 g, excess) wasadded to this mixture. Then 3-nitrophthalonitrile (1.00 g,5.78 mmol) was added to this mixture dropwise by stirringeffectively at 40 C under the N2 atmosphere. The reaction mixturewas kept for 3 day at this temperature under N2 atmosphere. Afterthe reaction mixture was cooled to room temperature, it waspoured into ca. 200 cm3 ice-water media. The occured precipitatewasfiltered and then washed with ca. 100 cm3 water up to thewashings became neutral. The occured precipitate wasfiltered anddissolved in CHCl3 and washed with%5 NaHCO3 to eliminate thebeginning residual compounds. The creamy solution was thentreated with anhydrous Na2SO4 until become dry andfiltered. Itwas purified by chromatography over a silica gel column by using aeluent that is a mix of CHCl3: MeOH (100/5), giving white powder,(1). Finally, the pure powder was dried in a vacuo. Yield of (1): 1.28 g (83%); m.p. = 119 C; Anal. Calcd forC15H10N2OS (266 g mol1C, 67.65; H, 3.78; N, 10.52 Found: C,67.58; H, 3.52; N, 10.30. FT-IR (cm1); 3068 (w, Ar-CH), 2922 (w,Alip-CH), 2228 (CRN, st), 1610(CC), 1567 (CN), 1484(st), 1273(Ar-S-Alip-CH), 1088, 1009, 985, 847, 795. 1H NMR (DMSO-d6) delta:8.11 (t, 1H, meta to Ar-O-Ar and CN), 7.88 (d, 1H, ortho to Ar-O-Ar),7.52 (d,1H, ortho to CN), 7,367.01 (m, 4H, O-Ar-S) 2.23(s, 3H, CH3-S-Ar). 13C NMR (DMSO-d6) delta: 165.4, 156.7, 141.4, 141.1, 133.5, 133.4,127.1, 126.3, 121.2, 121.1, 118.8, 110.2, 20.4. EI/MS m/z: 266.12 [M]+.

The synthetic route of 51762-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guensel, Arma?an; Guezel, Emre; Bilgicli, Ahmet T.; ?i?man, ?lkay; Yarasir, M. Niluefer; Journal of Photochemistry and Photobiology A: Chemistry; vol. 348; (2017); p. 57 – 67;,
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21524-39-0, name is 2,3-Difluorobenzonitrile, 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. Formula: C7H3F2N

Potassium nitrate (404 mg, 4.0 mmol) to a solution of 2,3- difluorobenzonitrile (278 mg, 2.0 mmol) in sulfuric acid (2 mL) at 00C. After stirring at 00C for 2 h the reaction was quenched with ice water (5 mL). The mixture was extracted with ethyl acetate (3×10 mL). The organic layer was dried and concentrated to give the crude product which was purified by silica gel (PE : EA = 40 : 1) to give the title compound as a yellow solid. (40 mg, 11%). 1H NMR (400 MHz, CDCl3): delta 8. 25-8.22 (m, IH), 7.69-7.63 (m, IH). LC/MS: m/e = 185 (M+H)+.

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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Electric Literature of 149793-69-1, These common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, 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: General procedure for nucleophilic substitution: A solution of 3-fluoro-5-trifluoromethyl-benzonitrile (1 eq) and the corresponding amine (3eq) in DMA was stirred at 145C during 3h. NaCl(aq) was added. The product was taken off into ethyl acetate. The organic layer was washed two times with water then dried over Na2S04 and evaporated under reduced pressure to give the intermediate compounds.

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIBASE PHARMA; CHEVE, Gwenael; DAYDE-CAZALS, Benedicte; FAUVEL, Benedicte; BORIES, Cedric; YASRI, Abdelaziz; WO2014/102377; (2014); A1;,
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Reference of 6136-93-2, 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 6136-93-2 as follows.

(iii) 2.2-Diethoxyethanethioamide(See, for example, Inami, K., Shiba, T., Bull. Chem. Soc. Jpn., 1985, 58, 352.) Diethoxyacetonitrile (0.050 g, 0.5 mmol; see step (ii) above) was placed in a 10 mL microwavable vial, methanol (5 mL) and (NEU)2S (54 muL, 0.5 mmol (40% wt solution in water)) was then added. The vial was then heated to 8O0C at IOOW for 15 min and the reaction then allowed to cool to RT. The solvent was then removed under reduced pressure and the residue dissolved in ethyl acetate (15 mL) and extracted with water (2 x 10 mL) and brine (2 x 5 mL). The organic layer was then dried (MgSO4), filtered and concentrated under reduced pressure to yield the sub-title compound as a white/off- white solid (0.081 g, 99%). m.p. = 92-94C. V1113x KBr/cm”1: 3335, 3171 upsilon(N-H), 2976, 2885 upsilon(C-H), 2247 upsilon(N?C), 1645, 1449 upsilon(C=S), 1019 delta(C-O). deltaH 1H(CDCl3): 1.26 (6H5 1, 2(CH3) (J=8.0Hz)), 3.71 (4H, m, 2(CH2)), 5.05 (IH, s, C-H), 7.70 (2H, d, N-H).

According to the analysis of related databases, 6136-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF STRATHCLYDE; WO2008/38018; (2008); A1;,
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Application of 5332-06-9, 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. 5332-06-9, name is 4-Bromobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 2-(benzylamino)acetate (50 g, 258.7 mmol) and K2C03 (71.5 g, 517.5 mmol) in MeCN (500 mL) was added 4-bromobutyronitrile (28.7 mL, 284.6 mmol)dropwise. The mixture was heated to 80 C for 12 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 5 : 1) to give the title compound (56 g, 83%) as light yellow oil. ?H NMR (400 IVIFIz, CDC13) 7.37 – 7.28 (m, 5H),4.18 (q, J 7.2 Hz, 2H), 3.80 (s, 2H), 3.32 (s, 2H), 2.80 (t, J= 6.4 Hz, 2H), 2.47 (t, J= 7.2 Hz,2H), 1.87 – 1.77 (m, 2H), 1.29 (t, J= 7.2 Hz, 3H).

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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120315-65-3, name is 4-Bromo-3-methoxybenzonitrile, 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: 120315-65-3

Step 1: tert-Butyl (1-(4-((4-cyano-2-methoxyphenyl)ethynyl)phenyl)cyclobutyl)carbamate: To a solution of 4-bromo-3-methoxybenzonitrile (1.92 g, 7.075 mmol) in anhydrous triethylamine (8 mL) and 1 ,4-dioxane (8 mL) was added bis(tert- butylphosphine)palladium(O) (0.144g, 0.283mmol) and copper(l) iodide (13 mg,0.094mmol). The reaction mixture was then degassed with N2 for 10 minutes before being cooled to 0C. A solution of ferf-butyl 1 -(4-ethynylphenyl)cyclobutylcarbamate (1.00 g, 4.72 mmol) in TEA (8 mL) was added dropwise to the cooled reaction mixture. The reaction was allowed to warm to RT and stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue diluted with DCM (20 mL) and filtered through Celite. The resulting filtrate was concentrated in vacuo to afford a brown oil that was purified by silica gel chromatography (ethyl acetate/hexane gradient, 0?50%) yielding the title compound as an off-white solid (890 mg, 47%). 1H NMR (500 MHz, CDCI3): delta 7.55-7.53 (m, 3H), 7.43 (d, 2H), 7.23 (d, 1 H), 7.12 (s, 1 H), 5.25 (s, 1 H), 3.94 (s, 3H), 2.54-2.51 (m, 4H), 2.1 1-2.13 (m, 1 H), 1.90-1.86 (m, 1 H), 1.34-1.25 (br s, 9H).

The synthetic route of 120315-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
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14447-18-8, name is Benzyl cyanoacetate, 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 C10H9NO2

A. 2-Cyano-4-ethyl-hex-2-enoic acid benzyl ester To a mixture of 2-ethylbutyraldehyde (2.0 mL, 16.2 mmol) and benzyl cyanoacetate (2.85 g, 16.2 mmol) at 0 C. was added acetic acid (0.1 mL, 1.62 mmol), then piperidine (0.16 mL, 1.62 mmol) dropwise. The ice bath was removed, and stirring continued for 10 minutes. Additional acetic acid (0.1 mL) and piperidine (0.16 mL) were added, followed by the additional of oven-dried 4A molecular sieves such that stirring was not impeded. The mixture was stirred 1.5 h, then partitioned between EtOAc and sat. NaHCO3 (aq). The phases were separated, and the organic phase washed with brine, dried (MgSO4), and concentrated to provide 3.96 g (95%) of 2-cyano-4-ethyl-hex-2-enoic acid benzyl ester as a colorless oil. 1H NMR (CDCl3) delta 7.39 (m, 6H), 5.28 (s, 2H), 2.60 (m, 1H), 1.62 (m, 2H), 1.40 (m, 2H), 0.88 (t, J=7.6 Hz, 6H). 13C NMR delta 168.69, 161.40, 135.01, 128.90, 128.82, 128.50, 114.11, 109.94, 68.07, 46.35, 27.30, 11.95. IR (neat) 2233, 1729 cm-1. LRMS: m/z 256.1 (M-1). Anal. Calcd for C16H19NO2: C, 74.68; H, 7.44; N, 5.44. Found: C, 74.75; H, 7.52; N, 5.50.

The synthetic route of 14447-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schwarz, Jacob Bradley; Wustrow, David Juergen; US2004/147608; (2004); A1;,
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Reference of 94088-46-7, A common heterocyclic compound, 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, molecular formula is C8H6FNO, 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.

Step 1 : A solution of 2-fluoro-6-methoxybenzonitrile (10 g, 66.2 mmol) in (0490) trifluoromethanesulfonic acid (100 mL) at 0C was treated with N-bromosuccinimide (12.4 g, 69.5 mmol) and the mixture was allowed to warm to RT and was stirred for 3 days. The reaction mixture was cooled to 0 C, quenched with ice, and made basic with 6 M KOH, and the resulting solid was collected by filtration. The filter cake was dissolved in ethyl acetate and dried over sodium sulfate, and the mixture was filtered. The filtrate was concentrated to afford an approximately 1 :1 mixture of 3-bromo-6-fluoro-2-methoxybenzonitrile and 3-bromo-2-fluoro- 6-methoxybenzonitrile, which was used in the next step without purification or analysis.

The synthetic route of 94088-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BURSULAYA, Badry; FISCH, Andreas; LAJINESS, James Paul; MACHAUER, Rainer; MALEKAR, Swapnil; PETRASSI, Hank Michael James; RAMAZANI, Farshad; REMOND, Anne-Catherine; ULLRICH, Thomas; USSELMANN, Peggy; VANGREVELINGHE, Eric; (145 pag.)WO2018/55550; (2018); A1;,
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Electric Literature of 873-74-5, These common heterocyclic compound, 873-74-5, name is 4-Aminobenzonitrile, 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: All acyl chloride solutions were freshly prepared in acetonitrile (ACN) at 1 mg/mL. All amine solutions were freshly prepared in water (H2O) at 1mg/mL. A portion of each acyl chloride solution was mixed with an amine solution with an equal volume and the mixture was allowed to stand for about 10 min. Each mixture was diluted with ACN 10-fold for analysis.

The synthetic route of 873-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zu, Chengli; Mukhopadhyay, Sukrit; Hanley, Patrick S.; Xia, Shijing; Bell, Bruce M.; Grigg, David; Gilbert, Jeffrey R.; O?Brien, John P.; Journal of the American Society for Mass Spectrometry; vol. 27; 5; (2016); p. 917 – 926;,
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Adding a certain compound to certain chemical reactions, such as: 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, 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 50594-78-0, COA of Formula: C7H3FN2O2

To a solution of 5-fluoro-2-nitrobenzonitrile (1 g, 6 mmol) and 3,5- difluorobenzenethiol (1.03 g, 7.05 mmol) in DIVIF (20 mL), was added K2C03 (2.5 g, 18 mmol). The reaction was stirred at 80 C for 1.5 hrs. The residue was poured into H20 (20 mL) and the aqueous phase was extracted with EA (30 mL x2). The organic layer was washed with brine (25 mL), dried over Na2SO4 and concentrated. The residue was purified by silica gel column (PE/EA = 3/1) to give 5-((3,5-difluorophenyl)thio)-2-nitrobenzonitrile (1.4 g, yield: 90%) as a yellow 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, 5-Fluoro-2-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
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