Category: chlorides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 1205-71-6, name is 4-Chloro-N-phenylaniline, 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 1205-71-6, Formula: C12H10ClN

Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyc.ohexyl)methyl 4- chlorophenyl(phenyl)carbamate.4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), NN-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 C overnight. HPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (40 C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by HPLC peak area. LCMS m/z = 374.3 [M+H]+; NMR (400 MHz, DMSO-i/6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 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, 4-Chloro-N-phenylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; BLACKBURN, Anthony C.; SHAKYA, Sagar Raj; DEMATTEI, John A.; CHUANG, Tsung-Hsun; WO2011/37613; (2011); A1;,
Chloride – Wikipedia,
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Electric Literature of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

C. 2-Trichloromethyl-5-(2-trifluoromethoxy-phenyl)-lH-benzimidazole(3-tert-Butoxycarbonylamino-2′-trifluoromethoxy-biphenyl-4-yl)-carbamic acid tert-butyl ester (573 mg, 1.22 mmol, as prepared in the previous step) was placed in a 40 mL vial equipped with a magnetic stir bar. DCM (10 mL) and TFA (5 mL) were added, and the mixture stirred at rt for 12 h. The solvent was removed under reduced pressure, and the residue was dissolved in DCM and washed with 2M aq NaOH. The organic extract was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in AcOH (5 mL) and placed in an 8 mL vial equipped with a magnetic stir bar. The mixture was cooled to 0 0C, treated with methyl-2,2,2-trichloroacetimidate (0.167 mL, 1.35 mmol) via syringe, and stirred at rt for 3 days. The solvent was removed under reduced pressure. The crude product was purified by column chromatography using a 12-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 2:5, v/v over 30 min, yielding 409 mg (85 %) of the desired compound. 1H-NMR (400 MHz, d4-MeOH) delta: 7.71 – 7.77 (m, 2H), 7.52 – 7.57 (m, IH), 7.39 – 7.51 (m, 4H).

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PLAYER, Mark, R.; PARKS, Daniel, J.; PARSONS, William; MEEGALLA, Sanath, K; ILLIG, Carl, R.; BALLENTINE, Shelley, K.; WO2010/45166; (2010); A1;,
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Some common heterocyclic compound, 63857-00-1, name is N-((2-Chloro-3-((phenylimino)methyl)cyclohex-2-en-1-ylidene)methyl)aniline hydrochloride, molecular formula is C20H20Cl2N2, 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: N-((2-Chloro-3-((phenylimino)methyl)cyclohex-2-en-1-ylidene)methyl)aniline hydrochloride

3.6 g 4-dimethylaminopyridine and 11. 8 g dye A (both available from Aldrich) were added under stirring to 60 ml Downanol PM in a 0. 5 1 three-necked flask equipped with a stirrer and a reflux condenser. Then 11.8 g 2-methylene-1, 3,3-trimethylindoline (Fischer base, available from Aldrich) was added under stirring for one minute to this suspension. The reaction mixture was heated to 80C for 2 hours. Then the reaction mixture was left to cool to room temperature and 200 ml of a 1 wt. -% hydrochloric acid were added. After the reaction mixture had cooled to room temperature, the insoluble portion was separated by filtration and washed with 0.5 1 of water. Then the product was dried for one day at 50C in a circulating air oven. Yield: 15.6 g (81.0 % based on dye A). The dried product was suspended in 150 ml methyl ethyl ketone and heated to 80C for one hour. Subsequently, the solution with a temperature of about 40C was filtered and the solid portion was washed with ethyl acetate. The product was air-dried. The yield after clean-up WAS 78 WT. -%; UV/VIS SPECTRUM IN METHANOL : 786 NM, EXTINCTION COEFFICIENT E = 381 1/G X CM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 63857-00-1, its application will become more common.

Reference:
Patent; KODAK POLYCHROME GRAPHICS GMBH; WO2004/52995; (2004); A1;,
Chloride – Wikipedia,
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Related Products of 96558-78-0, 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. 96558-78-0, name is 3-Bromo-5-chlorophenylamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-5-chloro-aniline (280 mg, 1.36 mmol) in l,4-dioxane (5 ml) and H20 (0.5 ml) was added 4,4,5,5-tetramethyl-2- [ 1 -methylprop- 1 -enyl]- 1 ,3 ,2-dioxaborolane (296 mg, 1.63 mmol), Pd(dppf)Cl2 (99 mg, 0.14 mmol) and Cs2C03 (1.33 g, 4.07 mmol) under N2. The mixture was heated at 130 C for 12 h under N2. The solution was filtered and concentrated in vacuo. The residue was purified by FCC (25 % EtOAc in petroleum ether) to give the title compound as a green oil (Y = 81 %). LC- MS (ESI): m/z: [M+H]+ = 182.1

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-chlorophenylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Recommanded Product: 13745-86-3

The typical procedure for the iron-catalyzed cross-coupling reaction of imidoyl chlorides with alkylmagnesium halide was applied to form the title compound and the following reagents were employed: ll-chloro-dibenzo[b,fj[l,4]thiazepine ( 49 mg, 0.20 mmol), Fe(acac)3 (3.53 mg, 0.001 mmol), THF (2 mL) and N-methylpyrrolidone (0.2 mL), cyclohexyl magnesium chloride (2 M in Et2O, 0.20 mL, 0.40 mmol). Purification by flash chromatography (ethyl acetate/heptane 1:4) afforded 51.9 mg (89%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): delta 7.45-7.43 (IH, m), 7.04-7.36 (2H, m), 7.33-7.21 (4H, m), 7.16 (IH, d, J = 8.0, 1.6Hz), 7.02-6.98 (IH, m), 2.86 (IH, tt, J = 11.2, 3.2Hz), 2.19-2.15 (IH, m), 1.96-1.92 (IH, m), 1.86-1.70 (4H, m), 1.45-1.26 (4H, m).I3C NMR (100 MHz, CDCl3): delta 176.7, 149.0, 141.2, 139.4, 132.4, 131.8, 130.2, 129.1, 128.9, 128.5, 127.4, 125.4, 125.1, 49.1, 32.6, 30.2, 27.0, 26.4, 26.2.

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; ACADIA PHARMACEUTICALS INC.; WO2007/47776; (2007); A1;,
Chloride – Wikipedia,
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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 10061-02-6 as follows. SDS of cas: 10061-02-6

Example 15: N-((S)-2-Amino-l-hydroxycarbamoyl-2-methyl-propyl)-4-((E)-7-hydroxy- hept-2-en-4-ynyIoxy)-benzamide (Compound 15); 15Step 15-A:To a solution of trans- 1,3 -dichloropropene (2.19 g, 19.7 mmol), potassium carbonate (3.63 g, 26.3 mmol), and potassium iodide (0.109 g, 0.657 mmol) in acetonitrile (200 mL) was added methyl-4-hydroxybenzoate (2.0 g, 13.2 mmol). The reaction was stirred at 80 0C for 4 hr after which it is quenched with brine, extracted with ethyl acetate, and washed with water. Organic phase dried with anhydrous magnesium sulfate, filtered, concentrated followed by purification with silica-gel chromatography (0-50% Ethyl Acetate/Heptane) to afford 15b (2.77 g). Found m/z ES+ = 227.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; DOBLER, Markus, Rolf; LENOIR, Francois; PARKER, David, Thomas; PENG, Yunshan; PIIZZI, Grazia; WATTANASIN, Sompong; WO2010/31750; (2010); A1;,
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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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6BrClO

Step 2 Preparation of 3-chloro-4-methoxyphenylboronic acid Following the general procedure outlined in Synthetic Scheme I, 10.2 g (46.2 mmol) of 4-bromo-2-chloroanisole (Step 1) was converted to 3-chloro-4-methoxyphenylboronic acid: NMR (CDCl3) delta 3.83 (s, 3H), 6.57 (s, 2H), 6.83 (d, J=8 Hz, 1H), 7.64 (dd, J=1.5, 8 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H).

According to the analysis of related databases, 50638-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; G.D. Searle & Co.; US5739166; (1998); A;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

EXAMPLE 1N2-((15)-l-cyclohexylethyl)-N4-(3-cyclopropyl-/H-pyrazol-5-yl)pyrrolo[2,l-J] [l,2,4]triazine-2,4-diamineIA. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo[l,2- f [l,2,4]triazin-4-amine[0078] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in z-PrOeta (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold /-PrOH and dried under vacuum to afford IA as a solid (1.3 g, 90%). HPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37 ‘. EXAMPLE 43 2-((4-((3-cyclopropyl-lH-pyrazol-5-yl)amino)pyrrolo[2,l-/| [l,2,4]triazin-2- yl)amino)-N-l,3-thiazol-2-ylacetamide43 A. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo [1,2- /][l,2,4]triazin-4-amine [0085] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOeta and dried under vacuum to afford 43A as a solid (1.3 g, 90%). etaPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/21859; (2008); A1;,
Chloride – Wikipedia,
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Related Products of 104-11-0, The chemical industry reduces the impact on the environment during synthesis 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 22 (0.80 g, 5.13 mmol) and K2CO3 (0.95 g, 6.85 mmol) in anhydrous acetonitrile (200 mL) at 0 C, was added crude 21(m) (0.77 g, 3.43 mmol), and the reaction heated and allowed to progress under reflux for 6 h. Acetonitrile was then removed under reduced pressure and the reaction mixture worked up with ethyl acetate (100 mL) and saturated aqueous Na2CO3 (3 × 50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography using mixtures of ethyl acetate:hexane (5:95) to (20:80) as eluent to give12(m)a as a yellow oil (0.63 g, 61%); 1H NMR (CDCl3, 300 MHz) delta 7.36-7.31 (7H, m, ArH), 7.22 (1H, m, H-3), 4.35 (1H, s, H-1), 3.54 (2H, s, H-8), 3.50 (2H, s, H-10), 2.19 (3H, s, N-CH3); 13C NMR (CDCl3, 75 MHz) delta 139.4 (Arqu), 137.7 (Arqu), 135.3 (Arqu), 132.6 (Arqu), 130.1 (C-12/16), 128.8 (C-13/15), 128.7 (ArC-H), 128.6 (ArC-H), 128.3 (ArC-H), 126.9 (ArC-H), 61.5 (C-8), 61.0 (C-10), 54.7 (C-1), 42.1 (N-CH3); HRMS (ES): Found 301.1221 (M + H)+: C16H18ClN4 (M + H)+ requires 301.1215.

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, 1-(4-Chlorophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zishiri, Vincent K.; Hunter, Roger; Smith, Peter J.; Taylor, Dale; Summers, Robert; Kirk, Kiaran; Martin, Rowena E.; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1729 – 1742;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 115843-99-7, name is 4-Bromo-3-chloro-2-fluoroaniline, molecular formula is C6H4BrClFN, 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. Safety of 4-Bromo-3-chloro-2-fluoroaniline

To a solution of 4-bromo-3-chloro-2-fluoroaniline (25 g, 111 mmol) and di-iso-propylethylamine (48.5 ml, 278 mmol) in DCM (250 mL) cooled in an ice bath was added acetic anhydride (11 .05 ml, 117 mmol)over 1.5 h. The reaction was warmed to RT and stirred for 24 h. The reaction was washed with HCI (1 M, 250 mL), NaHCO3 (150 mL) and water (100 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient elution, 0-40% EtOAc/petrol) to give the title compound (23.8 g). 1H NMR (500 MHz, DMSO-de) 9.97 (5, 1H), 7.95-7.77 (m, 1H), 7.56 (dd, 1H), 2.10 (5, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 115843-99-7, its application will become more common.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; TAIHO PHARMACEUTICAL CO., LTD.; JOHNSON, Christopher Norbert; BUCK, Ildiko Maria; CHESSARI, Gianni; DAY, James Edward Harvey; FUJIWARA, Hideto; HAMLETT, Christopher Charles Frederick; HISCOCK, Steven Douglas; HOLVEY, Rhian Sara; HOWARD, Steven; LIEBESCHUETZ, John Walter; PALMER, Nicholas John; ST DENIS, Jeffrey David; TWIGG, David Geoffrey; WOODHEAD, Andrew James; (377 pag.)WO2019/167000; (2019); A1;,
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