Month: September 2021

Synthetic Route of 67952-93-6,Some common heterocyclic compound, 67952-93-6, name is 3-Chloro-4-methylbenzylamine, molecular formula is C8H10ClN, 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.

1,4-Dichlorophthalazine-6-carbonitrile and 3-chloro-4-methylbenzylamine were stirred at room temperature in 1-methyl-2-pyrrolidinone in the presence of DBU, whereby the title compound was obtained as a less polar compound. 1H-NMR (400 MHz, DMSO-d6) delta; 2.29 (3H, s), 4.73 (2H, d, J=5.2 Hz), 7.28-7.32 (2H, m), 7.45 (1H, d, J=0.8 Hz), 8.20 (1H, dd, J=8.4, 0.4 Hz), 8.34 (1H, d, J=8.4, 1.6 Hz), 8.52 (1H, t, J=5.2 Hz), 9.00 (1H, m).

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-4-methylbenzylamine, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US6498159; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 5719-08-4, 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. 5719-08-4, name is 4-Chloro-9H-pyrimido[4,5-b]indole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8/V-methyl-4-(4-morpholinyl)-3-(1 H-pyrimido[4,5-6]indol-4-ylamino)bentrifluoroacetate?TFA4-Chloro-1 H-pyrimido[4,5-6]indole (0.080 g, 0.393 mmol), 3-amino-/v-methyl-4-(4- morpholinyl)benzenesulfonamide (0.128 g, 0.471 mmol), silver tnfluoromethanesulfonate (0.151 g, 0.589 mmol) and A/-Methyl-2-pyrrolidone (NMP) (1.0 mL) were combined in a microwave vessel and heated in the microwave at 180 C for 40 minutes. The reaction was filtered and purified via reverse phase HPLC (Waters Sunfire, 30x100mm column, 26-60% Acetonitrile/Water with 0.1 % TFA) to afford A/-methyl-4-(4-morpholinyl)-3-(1 H- pyrimido[4,5-6]indol-4-ylamino)benzenesulfonamide (0.049 g, 28% yield).

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-9H-pyrimido[4,5-b]indole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; ZHAO, Yongdong; WO2011/56739; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1005-56-7, A common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

6b (100 mg, 0.30 mmol) was dissolved in 5 mL of acetonitrile,4-Dimethylaminopyridine (162 mg, 1.33 mmol) andThiocarbazoformate (0.1 mL),After stirring at 0-60 C for 2-12 hours, the reaction solution was filtered,Concentrated, separated by column (n-hexane / ethyl acetate: 20/1)To give colorless oil 9 (122 mg, 0.26 mmol, 86%).

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Xie Weijia; Zhang Chenxi; Wang Zihao; Wu Xiaoming; Xu Jinyi; Yao Hequan; Lin Aijun; (12 pag.)CN107043403; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2613-34-5, name is 3-Chloro-2,4-difluoroaniline, 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. Quality Control of 3-Chloro-2,4-difluoroaniline

Et3N (0.19 mL, 1.35 mmol) was added to 3-fluoro-1-methyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid (146 mg, 0.46 mmol), HATU (218 mg, 0.57 mmol)2,4-difluoroaniline (119.8 mg, 0.92 mmol) in DMF (1 mL, 12.92 mmol) and stirred at 65Covernight. The solution was directly charged on a silica gel column and purified by column chromatography using a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and the residue was crystallised from methanol (10 mL) upon addition of water. The white crystals were filtered off and dried at 50C overnight, resulting in compound 312 (105 mg). Method D: Rt: 1.88 mm mlz: 428.0 (M-H) Exact mass: 429.1. Differentialscanning calorimetry: From 30 to 300 C at 10C/mm: peak at 179.4C.?H NMR (400 MHz, DMSO-d6) oe ppm 1.18 (d, J=7.0 Hz, 3 H), 3.81 (s, 3 H), 3.91 – 4.03 (m, 1 H), 7.07 – 7.14 (m, 1 H), 7.31 – 7.39 (m, 1 H), 7.54 (d, J=4.6 Hz, 1 H), 7.63 – 7.72 (m, 1 H), 8.59 (d, J=8.8 Hz, 1 H), 9.69 (s, 1 H).

The synthetic route of 2613-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-02-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2106-02-7 name is 2-Chloro-4-fluoroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Concentrated nitric acid (8.8 g, 91 mmol) was added drop wise over 30 min to a stirred solution of 2-chloro-4-fluoro-phenylamine (12 g, 82.3 mmol) in cone H2SO4 acid (100 mL) at -10 0C. The mixture was stirred at that temperature for 10 min. Then the reaction mixture was poured into cooled EtOAc, and ice water was added. The organic layer was separated and washed with brine and saturated NaHCO3 solution, dried (MgSO4) and concentrated in vacuo. Recrystallization (ethyl ether) provided 2-chloro-4-fluoro-5-nitroaniline (5.0 g, 32% yield). 1H NMR (400 MHz, DMSO-rftf): (57.59 (d, J= 11.2 Hz, 1 H)5 7.48 (d, J= 7.2 Hz, 1 H), 5.84 (s, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2008/33999; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13078-79-0,Some common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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.

Methyl (3-chlorophenethyl)carbamate (I-45) The title compound was prepared according to the general procedure C using 2-(3-chlorophenyl)ethan-1-amine (70 muL, 0.40 mmol, 1 eq), methylchloroformate (58 muL, 0.75 mmol, 1.5 eq) and DiPEA (174 muL, 2.0 mmol, 2 eq). Column chromatography (20% -> 40% EtOAc/pentane) afforded the product (67 mg, 0.31 mmol, 77%). TLC: Rf = 0.7 (30% EtOAc/pentane). 1H NMR (400 MHz, CDCl3) delta 7.25 – 7.15 (m, 3H), 7.11 – 7.03 (m, 1H), 4.89 (br s, 1H), 3.65 (s, 3H), 3.41 (q, J = 6.8 Hz, 2H), 2.78 (t, J = 7.1 Hz, 2H). 13C NMR (101 MHz, CDCl3) delta 157.05, 140.94, 134.37, 129.90, 128.93, 127.04, 126.75, 52.15, 42.04, 35.90. HRMS [C10H12ClNO2 + H]+ : 214.0629 calculated, 214.0630 found (Delta = 0.14 ppm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Chlorophenyl)ethanamine, its application will become more common.

Reference:
Patent; Universiteit Leiden; The designation of the inventor has not yet been filed; EP3575287; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 328-84-7, 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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a. 1,3-Bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene A solution of potassium hydroxide (3.26 g. 0.05 mole, 85%) in water (~3 g.) is added slowly dropwise to a solution of resorcinol (2.75 g. 0.025 mole) and 3,4-dichloro-alpha,alpha,alpha-trifluorotoluene (10.75 g. 0.05 mole) in sulfolane (125 ml) at 150-160 C., with stirring. When the addition is complete, the strongly colored reaction mixture is stirred at 150-160 C. overnight, then cooled, diluted with benzene (200 ml), and washed cautiously with water (700 ml). Hexane (200 ml) is added and the mixture washed with water (600 ml), dilute sulfuric acid (600 ml), dilute sodium hydroxide solution (600 ml), and water (600 ml), dried, and the solvent removed to give 1,3-bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene (8.6 g 65%) b.p. 160-70 C./0.1 mm.

The synthetic route of 3,4-Dichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US4046798; (1977); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Difluorobenzene-1-sulfonyl chloride

Into a microwave reaction vessel were combined (3-Amino-2,6-difluoro-phenyl)-(5-chloro- lH-pyrrolo[2,3-b]pyridin-3-yl) -methanone (P-1801, 50 mg, 0.16 mmol, prepared as described in Example ???), 3,5-difluorobenzenesulfonyl chloride (610, 103 mg, 0.49 mmol), pyridine (0.5 mL, 6.1820 mol) and tetrahydrofuran (3.0 mL,). The reaction was warmed in the CEM microwave at 300 watts, 130 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The compound (P- 1841) was isolated using column chromatography (silica, hexane:ethyl acetate 70:30) to obtain 36 mg (46%) compound. MS = 482.0.

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; PLEXXIKON, INC.; WO2007/2325; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-44-5,Some common heterocyclic compound, 1435-44-5, name is 1-Chloro-2,4-difluorobenzene, molecular formula is C6H3ClF2, 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.

(3-Chloro-2,6-difluoro-phenyl)-methanol (G=Cl, G’=H. G”=F) The title compound was prepared from 1-chloro-2,4-difluoro-benzene by a procedure analogous to that for (2,6-difluoro-4-methyl-phenyl)-methanol, above. 1H NMR (400 MHz, CDCl3) delta1.90 (t, J=6.4 Hz, 1H), 4.78 (d, J=6.4 Hz, 2H), 6.87 (app. dt, J=1.8, 8.9 Hz, 1H), 7.32 (app. dt, J=5.8, 2.8 Hz, 1H) ppm.

The synthetic route of 1435-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US6235764; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-3-methoxyaniline

Step 1(4-Chloro-3-methoxy-phenyl)-methyl-amineIn a 50 mL flask are added 4-Chloro-3-methoxy-phenylamine (907 mg), sodium methoxide (1.56 g), 10 mL anhydrous methanol, and paraformaldehyde (690 mg). Reaction mixture is then stirred overnight at room temperature. Then, paraformaldehyde (173 mg) and sodium methoxyde (311 mg) are added, and reaction mixture is heated at reflux for 1 hour. Sodium borohydride (436 mg) is then added, and reaction mixture is stirred at reflux for 4 hours. Once back at room temperature, mixture is partially evaporated, and KOH aq 1M (50 mL) is then added. The obtained suspension is extracted by Et20, organic phase is dried over Na2S04 and evaporated. The obtained residue is purified by flash chromatography (cHex to cHex/EtOAc 8/2) to give 650 mg of the expected product (66 %).MS [M+H]+ m/z = 171.9 1H-NMR (DMSO- 6) : delta (ppm) 2.66 (d, J = 4.9 Hz, 3H) ; 3.77 (s, 3H) ; 5.80 (q, J = 4.9 Hz, 1H) ; 6.09 (dd, J = 2.5 Hz, J = 8.7 Hz, 1H) ; 6.25 (d, J = 2.4 Hz, 1H) ; 7.04 (d, J = 8.7 Hz, 1H).

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; LASSALLE, Manuel; DUBANCHET, Barbara; WO2015/189330; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics