Month: February 2021

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. 1000339-52-5, name is 3-Fluoro-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Synthesis of 3-((3,5-dimethylphenyl)amino)-2-nitrobenzonitrile To 3,5-dimethylaniline (3.9 g, 32.2 mmol) in THF (90 mL) was added sodium hydride (95% in mineral oil, 1.23 g, 48.9 mmol) and stirred for 1 hour. 3-Fluoro-2-nitrobenzonitrile (4.3 g, 25.9 mmol) was added and the reaction mixture was heated to reflux for about 16 hours. Reaction mixture cooled to room temperature, then water was added and filtered through silica gel, washed with 5% THF in hexane and concentrated in vacuo. The crude mixture was purified by flash column chromatography with 10% THF in hexane to give orange powder which was recrystallised with 10% 1,2-dimethoxyethane in hexane to give 3-((3,5-dimethylphenyl)amino)-2-nitrobenzonitrile (3.8 g, 55% yield) as an orange powder.

The synthetic route of 1000339-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; KWONG, Raymond; LAM, Sze Kui; LAM, Siu Tung; TSANG, Kit Yee; LEE, Chi Hang; SZIGETHY, Geza; (159 pag.)US2016/218303; (2016); 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

4-Chloro-2-fluoro-benzonitrile (8.0 g, 50.4 mmol), NaHS^FbO (50.4 mmol, 4.006 g) and DMF (30 mL) were stirred on an ice bath for 1 h. The mixture was partitioned between diethyl ether and HC1 (0.5 M), the organic phase was then extracted with NaOH (2 M, 50 ml) and the aqueous phase was concentrated a little, then acidified with HC1 which gave a precipitate that was isolated and dried to afford the title compound (5.1 g, 59 %). ‘H NMR (400 MHz, Chloroform-^) d 7.53 (d, j= 8.4 Hz, 1H), 7.43 (d, j= 1.7 Hz, 1H), 7.22 (dd, j= 8.4, 1.8 Hz, 1H), 4.15 (s, 1H).

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; (118 pag.)WO2019/137971; (2019); A1;,
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Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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: 2-Fluoro-5-nitrobenzonitrile (1.4g, 1.0 eq, 8.4 mmol) was taken in annhydrous DMF (10 mL). Secondary amine (1.2 eq, 10.12 mmol) was added to the above solution followed by the addition of K2C03 (3.5g, 3.0eq, 25.3 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL) and partitioned with water (100 mL). Organic layers were separated and the aqueous layers were washed with EtOAc (1 x 50 mL). The combined oragnic layers were washed with aqueous staurated NaHC03 solution (100 mL) and dried over Na2S04. Organic layers were concentrated under reduced pressure to leave a crude mixture. The mixture was purified by column chromatography on silica gel (ISCO System) using EtOAc / Hexane (gradient system from 0: 1 to 2:8) as eluent to give the product as a solid. 2-(4-(Methylsulfonyl)piperazin-l-yl)-5-nitrobenzonitrile: Synthesized as described in Step-1. Yield = 73%, 1H NMR (300 MHz, CDC13) delta 8.43 (d, J = 2.1 Hz, 1H), 8.27 (dd, J = 9.3, 2.7 Hz, 1H), 6.98 (d, J = 9.3 Hz, 1H), 3.59 – 3.48 (m, 4H), 2.68 – 2.57 (m, 4H), 2.38 (s, 3H); LCMS (m z): 311 (M+H)+.

Statistics shows that 2-Fluoro-5-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17417-09-3.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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Application of 33279-01-5, 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. 33279-01-5, name is 3-Oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of 3-ethyl-l-(3-methylpyridm-2-ylHH-pyrazol-5-amine; EPO 3-Oxo-pentanenitrile (4.87 g, 26.10 mmol) and diphenylmethanone (3-methyl pyridin-2-yl)hydrazone (5.00 g, 17.40 mmol) were dissolved in anhydrous EtOH (150 mL). TsOH (3.31 g, 17.4 mmol) and cone. HCl (14.29 mL, 174.0 mmol) were added to the solution. The mixture was heated at reflux overnight. Additional 3-oxo-pentanenitrile (4.87 g, 26.10 mmol) was added. The mixture was refluxed another 24 h. EtOAc was added. The resulting mixture was basified by slow addition of sat. Na2CO3. The organic layer was dried over MgSO4 and then concentrated. Column chromatography purification (25% EtOAc/ hexane) afforded the title compound as a light yellow oil (1.5 g, 42.6%). 1H NMR (400 MHz, DMSO-d6) delta 8.35-8.34 (IH, d, J = 2.8 Hz), 7.86-7.84 (IH, d, J = 9.6 Hz), 7.39-7.36 (IH, t, J =4.5 Hz), 5.46 (IH, S), 2.58-2.52 (2H, q, J = 6.0 Hz), 2.30 (3H, s), 1.26-1.23 (3H, t, J = 4.2 Hz); LC-MS m/z 203.1 (MH+), HPLC RT (min) 1.07 {method (A)}.

The chemical industry reduces the impact on the environment during synthesis 3-Oxopentanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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These common heterocyclic compound, 72115-09-4, name is 5-Amino-2-bromobenzonitrile, 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. Formula: C7H5BrN2

5-amino-2-bromobenzonitriie (5.0 g, 25.4 mmoi), cyciopropyiboronic acid (4.36 g, 50.8 mmoi), cs2co3 (49.62 g, 152.3 mmoi), and tricyciohexyiphosphine (2.85 g, 10.2 mmoi) were weighed out and added to a large reaction tube with magnetic stir bar. Toiuene (120 mL) and water (40 mL) were added, and the reaction was subjected to yigorous sub-surface nitrogen sparging. Pd(OAc)2 (1.14 g, 5.1 mmoi) was weighed out and added, the tube was sealed under nitrogen, and the reaction was heated oyernight at 110 c. This was then filtered with water and ethyi acetate washings. The combined washings were treated with saturated aqueous NaHcO3 and the iayers were separated. The aqueous was extracted 4 more times with ethyi acetate, and the combined organie iayer was washed twice with brine and dried oyer sodium suifate. After filtration, concentration, and drying on the high yacuum, 7.65 g was obtained of 5-amino-2- cyciopropyibenzonitriie containing tricyciohexyiphosphine deriyed byproducts. This was used without further purification.

The synthetic route of 5-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; MCMURTRIE, Darren; KOLLURI, Rao; MASUDA, Esteban; TSO, Kin; ALVAREZ, Salvador; HECKRODT, Thilo; HOLLAND, Sacha; KELLEY, Ryan; DUNCTON, Matthew; SINGH, Rajinder; WO2014/89112; (2014); A1;,
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Related Products of 1897-52-5, These common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, 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.

Synthesis of compound 2.2. Compound 2.1 (5 g, 35.97 mmol, 1.00 eq), NH4C1 (2.11 g, 39.56 mmol, 1.1 eq) were suspended in toluene (100ml). A solution of trimethylaluminium (2.0 M, 19.5 ml, 39.56 mmol, 1.1 eq) was added dropwise to the above reaction mixture at room temperature. The mixture was stirred for one hour at ambient temperature and subsequently refluxed for 16 hours. After completion of the reaction, toluene was evaporated and residue was diluted with 10% methanol in CH2C12 (lOOmL). Silica gel (5.0 g) was added mixture and stirred for 30 minutes at ambient temperature. After 30 minutes, slurry was filtered and washed with CH2Cl2/methanol. The filtrate was concentrated under vacuum at 45 C to afford the crude material which was purified using trituration with 20% ethyl acetate in hexane (50ml). The solid obtained was filtered off and dried under vacuum to afforded pure compound 2.2 (4.5 g, 80.35 %). LCMS: 99.27%. MS (ES): m/z 157.0 (M+H)+.

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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Synthetic Route of 1021871-35-1, A common heterocyclic compound, 1021871-35-1, name is 3-Chloro-5-(hydroxymethyl)benzonitrile, molecular formula is C8H6ClNO, 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 4: 3-Chloro-5-cyanobenzyl carbonochloridate 3-Chloro-5-(hydroxymethyl)benzonitrile (25 g, 145 mmol) was dissolved in THF (200 mL). The resulting yellow solution was cooled to 10¡ã C. in an ice bath and treated dropwise with phosgene in toluene (152 mL, 289 mmol). The reaction mixture was stirred at ambient temperature for 16 hrs. The mixture was concentrated under reduced pressure and the crude material was diluted with toluene (200 ml) and re-concentrated under reduced pressure. The residue was purified by chromatography on silica (Redisep 340 g column on a Biotage system), eluting with EtOAc/iso-hexane to give 3-chloro-5-cyanobenzyl carbonochloridate as an oil. 1H NMR (600 MHz, CDCl3) delta 7.70 (1H, s), 7.66 (1H, s), 7.62 (1H, s), 5.32 (2H, s).

The synthetic route of 1021871-35-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Legrand, Darren Mark; Furminger, Vikki; Thomson, Christopher; Hughes, Owen Rhys; Stanley, Emily; US2014/171403; (2014); A1;,
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Synthetic Route of 874-89-5, These common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)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.

Preparation of Intermediate 2 (Int.2); N’-Hydroxy-4-(hydroxymethyl)benzimidamide; [00110] A solution of 4-(hydroxymethyl)benzonitrile (22.43g, 0.1685g), hydroxylamine hydrochloride (18.67g, 0.2689 mol) and NaHCO3 (45.22g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ~75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N’-hydroxy-4- (hydroxymethyl)benzimidamide (28.5g) as a white solid. The material was used without further purification. The compound had an HPLC retention time = 0.232 min. – Column: CHROMOLITH SpeedROD 4.6 x 50 mm (4 min.); Solvent A = 10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B = 90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1 = 167.3

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric, J.; PITTS, William, J.; WATTERSON, Scott, Hunter; WO2010/85584; (2010); A1;,
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Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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. Recommanded Product: 17626-40-3

Intermediate 44: (Trans)-N-(2-amino-5-cvanophenyl)-2-oxo-3-(2-pyridinyl)-1-oxa-3- azaspiro[4.51decane-8-carboxamide; To a shaken mixture of (trans)-2-oxo-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decane-8- carboxylic acid (Intermediate 45, 1 10 mg, 0.398 mmol) and 3,4-diaminobenzonitrile (commercially available, 80 mg, 0.597 mmol) in anhydrous pyridine (1.6 ml) was added EDCHCI (153 mg, 0.796 mmol) and the reaction mixture was shaken at room temperature for 1 hour. The mixture was concentrated under vacuum and the residue was partitioned between saturated sodium bicarbonate solution and EtOAc (2×10 ml). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give a residue which was purified by silica gel chromatography eluting with 40% Et2ODCM, Et2O 100% then 10% MeOHDCM to afford the title compound as solid (155 mg, 85%). 1 H-NMR (400 MHz, DMSO-d6): delta 1.59-1.79 (m, 4H), 1.93-2.02 (m, 2H), 2.03-2.10 (m, 2H), 4.03-4.07 (s, 2H), 5.92 (br s., 2H), 6.77 (d, 1 H), 7.13-7.18 (m, 1 H), 7.29 (d, 1 H), 7.62 (s, 1 H), 7.82-7.88 (m, 1 H), 8.1 1 (d, 1 H), 8.39 (d, 1 H), 9.09-9.16 (s, 1 H); UPLC-MS: 0.60 min, m/z 392 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17626-40-3, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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

General procedure: To the solution of NaOH (5.93 g, 0.15 mol) in water (20 mL) and ethanol (120 mL), hydroxylamine hydrochloride (10.33 g, 0.15 mol) was added in one portion at room temperature. The resulting mixture was then stirred for 10 min, followed by the addition of 4-substituted cyanobenzene (1, 0.12 mol) and then heated to reflux for 4 h. After cooled to room temperature, the reaction mixture was evaporated in vacuo to remove ethanol. The obtained slurry was dissolved in ethyl acetate and filtered. The filtrate was collected, dried over anhydrous Na2SO4, and then concentrated to give corresponding compound 2, which was used in next step without any purification.

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Hong; Chen, Jia; Li, Gang; Ge, Shushan; Shi, Yujun; Fang, Yuan; Ling, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 950 – 953;,
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