Category: 69411-05-8

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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 69411-05-8

Intermediate B (200 mg, 0.41 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (80 mg, 0.41 mmol) and DIEA (106 mg, 2 mmol) were dissolved in THF (20 ml_). The reaction mixture was heated to 85C for 18 hours. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent DCM:methanol 100. to 98:2) to followed by pre-HPLC to give the titled compound (14 mg, 5.8%) as a white solid. LCMS (method B): 2.66 min [MH]+=592.2. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.45 (s, 3 H) 5.81(d, J= 6.4 Hz, 1 H) 7.30 (m, 4 H) 7.43 (m, 3 H) 7.61 (d, J=8.8, 2 H) 7.90 (m, 4 H) 8.55 (s, 1 H) 9.18 (s, 1 H) 9.39 (s, 1 H) 9.57 (s, 1 H).

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 69411-05-8, 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

The synthetic route of 3-Chloro-5-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, belongs to chlorides-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. HPLC of Formula: C7H5ClF3N

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H5ClF3N

A 1.0 M solution of lithium bis(trimethyldisilyl)amide in THF (i3 mL, i2 mmol, 2.0 equiv) was added through an addition funnel at 10-i5 C to a solution of 3-chloro-5-(trifluoromethyl)aniline (i5 g, 78 mmol, i.2 equiv) in THF (i3 mL). The mixture was allowed to stir at room temperature for 20 mm and a solution of crude trans-i ?-tert-butyl-4?-ethyl-3 -iodo-2-oxo-[ i ,3 ?-bipiperidine]- i ?,4?- dicarboxylate 9 (3.7 g, 65 mmol, i.0 equiv) in THF (i3 mL) was added through an addition funnel at iO-i5 C over 30 mm. After addition, the reaction was allowed to stir at the temperature for 30 mm. Upon completion, the reaction was cooled to 5 C and quenched slowly with water (iO mL), keeping the temperature below 20 C. The quenched reaction was extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with saturated brine (30 mL), dried (Na2504), filtered, and concentrated in vacuo. The resulting crude product was purified over silica gel eluting with a gradient of iO% to 75% of EtOAc in heptanes to give the desire product iO. ESIMS (M+H-56): 463.i. ?H NMR (400 MHz, CDC13) 5. 6.92 (s, iH), 6.7i-6.69 (m, 2H), 4.i7- 4.06 (m, 4H), 3.78-3.68 (m, 2H), 3.46-3.36 (m, 3H), 3.23-3.07 (m, 2H), 2.73-2.65 (m, iH), 2.44-2.37 (m, iH), 2.03-i.85 (m, 3H), i.7i-i.6i (m, 2H), i.46 (s, 9H), i.27-i.i9 (m, 3H).

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; MACPHEE, J. Michael; NEUMAN, Linda L.; (89 pag.)WO2018/17153; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8,Some common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, molecular formula is C7H5ClF3N, 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: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-trifluoromethylaniline, its application will become more common.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, belongs to chlorides-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 69411-05-8, Quality Control of 3-Chloro-5-trifluoromethylaniline

To a stirred mixture of Preparation 65A (2.51 g, 12.9 mmoL) in EtOH (130 mL) was added acetic anhydride (15.0 mL, 159 mmoL). The mixture was stirred at room temperature for 17 h. The mixture was then poured into a mixture of 40 mL of ice, 10 mL of saturated NaHCCh solution and 60 mL of EtOAc. The aqueous layer was separated and extracted with EtOAc (1 x 60 mL). The combined EtOAc layers were washed with brine (Ix 20 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2.88 g of Preparation 65B in 94% yield. [00497] HPLC: 2.84 min (RT)(Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=238 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.4 (s, IH, NH) 7.96 (s, IH) 7.91 (s,l H) 7.50 (s, IH), 2.09 (s, 3H).

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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/3077; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, A common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, molecular formula is C7H5ClF3N, 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.

To a cold (0C) suspension of 3-chloro-5-(trifluoromethyl)aniline (1 g, 5.11 mmol, Eq: 1.00) and calcium carbonate (1.02 g, 10.2 mmol, Eq: 2) in water (11.1 ml) and dichloromethane (11.1 ml) was added thiophosgene (647 mg, 430 mu, 5.62 mmol, Eq: 1.1). The biphasic reaction mixture was allowed to warm to room temperature and was vigorously stirred for 16h. IN HC1 (10 mL) was added and the reaction mixture was pardoned between water and EtOAc. The organic layer was washed with water and brine, adsorbed unto silica (3g), and purified on silica gel (column 40 g, hexane/AcOEt 1:0 to 85: 15) to give 880 mg (72%) of the desired product as a colorless oil.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 69411-05-8, 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1 3-Chloro-5-(trifluoromethyl)benzenesulfonyl chloride [0115] [0116] A solution of NaNO2 (6.50 g) was added to a suspension of 3-chloro-5-(trifluoromethyl)aniline (18.44 g) in concentrated HCl/acetic acid (83 mL/30 mL) at 0 C. and the mixture stirred for one hour. The diazonium salt formed was transferred into a saturated solution of sulfur dioxide in glacial acetic acid (350 mL) at 0 C. and the mixture was warmed up to room temperature for one hour. The mixture was poured onto ice-water and extracted with diethyl ether. The combined organic layers were washed with sodium hydrogen carbonate, dried over sodium sulphate, concentrated and purified by silica chromatography eluting with ethyl actetate/hexane to yield 3-chloro-5-(trifluoromethyl)benzenesulfonyl chloride (22 g, 84%). [0117] 1H NMR (400 MHz, Chloroform-D) d ppm 8.0 (m, 1H) 8.2 (m, 1H) 8.2 (t, J=1.9 Hz, 1H).

The synthetic route of 3-Chloro-5-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMTED; Gleave, Robert James; Hachisu, Shuji; Page, Lee William; US2013/116270; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, These common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, 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.

Example 13 1-(5-Chloro-3-trifluormethyl-anilino)-4-(4-pyridyl-methyl)-phthalazine A suspension of 27.9 g (109 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 21.4 g (109 mMol) of 5-amino-3-chloro-benzotrifluoride (Example 5b) in 500 ml of ethanol and 27.4 ml of 4 N HCl/dioxane is stirred during 3 h a 80 C. After cooling down, the reaction mixture is diluted with 0.3 l of ether, filtrated, and washed with ether. The remaining solid is then taken up in water and EtOAc, brought to alkaline pH by means of NH3 solution, stirred for 15 min at room temperature and then filtered and washed with ether (?raw product). The water layer is removed from the filtrate and extracted twice with ethyl acetate. The organic layers are washed with water and brine, dried over Na2SO4 and evaporated. The residue is combined with the raw product mentioned above, and the solid is dissolved in ethyl acetate and methanol. About 100 g SiO2 are added, followed by evaporation, and the powder is applied onto a silica gel column and eluted with ethyl acetate and subsequently with a mixture of ethyl acetate and methanol (98:2?95:5, v/v). Solving the obtained fractions in ethyl acetate/methanol, partial evaporation and crystallization by addition of ether/hexane leads to the title compound: m.p. 231-232 C.; An. calc. (C21H14N4ClF3) C, 60.81%; H, 3.40%; N, 13.51%; Cl, 8.55%; F, 13.74%; An meas. C, 60.8%; H, 3.4%; N, 13.5%; Cl, 8.5%; F, 13.8%; 1H-NMR (DMSO-d6) 9.63 (s, HN), 8.60 (d, 1H), 8.56 (s, 1H), 8.44 (d, 2H), 8.39 (s, 1H), 8.16 (d, 1H), 8.03 (t, 1H), 7.97 (t, 1H), 7.43 (s, 1H), 7.32 (d, 2H), 4.63 (s, 2H); FAB-MS (M+H)+=415.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bold, Guido; Dawson King, Janet; Frei, Jorg; Heng, Richard; Manley, Paul William; Wietfeld, Bernhard; Wood, Jeanette Marjorie; US2003/13718; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 69411-05-8 as follows. Quality Control of 3-Chloro-5-trifluoromethylaniline

Intermediate E (120 mg, 0.25 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (49 mg, 0.27 mmol) and DMAP (16 mg, 0.125 mmol) were dissolved in THF (15 mL). The reaction mixture was heated to 85 C for 16 hours. The solvent was removed and the crude product was purified by column chromatography (DCM: methanol 100/0 to 98/2) to give 5-((4-((4-(3-(3-chloro-5- (trifluoromethyl)phenyl)ureido)phenyl)(methyl)amino)pyrimidin-2-yl) amino)-N,2- dimethylbenzamide (38 mg, 26%) as a white solid. LCMS (method B): 2.74 min [MH]+=584.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.23 (s, 3 H) 2.74 (d, J=4.8 Hz, 3 H) 3.41 (s, 3 H) 5.77 (d, J= 7.0 Hz, 1 H) 7.07 (d, J= 8.4 Hz, 1 H) 7.28 (d, J= 8.8 Hz, 2 H) 7.43 (s, 1 H) 7.59 (d, J= 8.8 Hz, 2 H) 7.67 (dd, J=8.4 2.0 Hz, 1 H) 7.87 (m, 4 H) 8.11 (m, 1 H) 9.15 (s, 1 H) 9.19 (s, 1 H) 9.37( s, 1 H).

According to the analysis of related databases, 69411-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics