Tag: M.W=100-200

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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

1-chloro-3,5-dimethoxybenzene (10.0 g, 58 mmol) and N-bromosuccinimide (10.3 g, 58 mmol)In 1,2-diethylene chloride (200 ml)After melting, the mixture is stirred at room temperature for 24 hours.After the reaction, the solvent was removed from the reaction solution through a rotary evaporator,After extraction with methylene chloride / distilled water, column chromatography was carried out using a methylene chloride / hexane mixed solvent as a developing solvent to obtain 13.3 g of intermediate 1

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; LG Chem, Ltd.; Dankook University Cheonan Campus Industry-Academic Cooperation Foundation; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Kim Gong-gyeom; Lee U-cheol; Lee Chil-won; Cha Jae-ryeong; Joo Yun-seok; (37 pag.)KR2019/109846; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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 B: Preparation of l-Chloro-3-fluoro-2-isothiocyanatobenzene To a solution of 2-chloro-6-fluorobenzenamine (5.0 g, 34 mmol) in chlorobenzene (52 mL) was added carbonothioic dichloride (thiophosgene) (5.1 g, 45 mmol) and DMF (0.27 mL). The reaction mixture was refluxed for 2 h and then concentrated to leave the title compound as a brown oil (6.15 g), which was used in Step C without further purification. H NMR 5 7.18 (m, 2H), 7.07 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluoroaniline, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; TAGGI, Andrew, Edmund; LONG, Jeffrey, Keith; BEREZNAK, James, Francis; WO2013/116251; (2013); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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. Quality Control of 1-(2-Chloroethyl)azepane hydrochloride

Example 7 1-(2-(1-Perhydroazepinyl)ethyl)-3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine A solution of 1-(2-chloroethyl)perhydroazepine hydrochloride (42 mg, 0.21 mmol) in N,N-dimethylformamide (1 mL) was treated with triethylamine (30 muL, 0.22 mmol) then transferred to a flask containing 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 45 mg, 0.176 mmol) in N,N-dimethylformamide (2 mL). Sodium iodide (32 mg, 0.21 mmol) and sodium hydrogencarbonate (18 mg, 0.21 mmol) were added and the resultant mixture was heated at 60¡ã C. overnight. The solvent was then removed in vacuo and the residue was partitioned between saturated aqueous sodium hydrogencarbonate solution (5 mL) and dichloromethane (5 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2*5 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by reversed phase preparative HPLC (condition 2) to give the acetate salt of the title compound. The free base was obtained by treating with dilute aqueous ammonia solution (2 mL) and extracting with ether (4*3 mL). Drying over Na2SO4, filtering and evaporation to dryness gave the title compound as a white solid (16 mg, 24percent). NMR (CDCl3, selected data for the free base): 0.8 (d, 3H), 1.35 (s, 3H), 1.6-1.8 (m, 9H), 2.10 (m, 1H), 2.4-2.5 (m, 2H), 2.6-3.0 (m, 11H), 7.25 (d, 1H), 7.35 (t, 1H), 7.55 (d, 1H), 7.85 (s, 1H), 7.95 (s, 1H). MS (thermospray): M/Z (MH+) 382.6; C23H35N5+H requires 382.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Reference:
Patent; Gibson, Stephen Paul; Tommasini, Ivan; Verrier, Kimberley; Dutton, Christopher James; Gethin, David Morris; Critcher, Douglas James; Armer, Richard Edward; US2003/4340; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference 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 33786-89-9, 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. 33786-89-9 name is 5-Chloro-m-phenylenediamine, 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.

EXAMPLE 1 In an autoclave, 3.3 g. of 3,5-diaminochlorobenzene, 0.2 g. of cuprous chloride and 10 g. of liquid ammonia were charged to react them at 170 to 175 C. for 5 hours. After the reaction, the unreacted ammonia was discharged and a greyish black crystal was obtained. The product was purified by a silica gel column chromatography to obtain 1.7 g. of 1,3,5-triaminobenzene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-m-phenylenediamine, and friends who are interested can also refer to it.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4380670; (1983); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2401-24-3, These common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-methoxyaniline, 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 113 4-(2-Chloro-5-methoxyanilino)-2,6-di(2-pyridinyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2,6-di(2-pyridinyl)pyrimidine (25 mg, 0.093 mmol) and 2-chloro-5-methoxyaniline (27 mg, 0.140 mmol) similar to Example 111 and isolated as a white solid (20 mg, 55%). 1H NMR (CDCl3): 8.87-8.82 (m, 1H), 8.72-8.64 (m, 3H), 8.08 (d, J=2.7 Hz, 1H), 7.92 (s, 1H), 7.90-7.86 (m, 2H), 7.45-7.38 (m, 3H), 7.33 (d, J=8.7 Hz, 1H), 6.67 (dd, J=3.0, 9.0 Hz, 1H), 3.91 (s, 3H).

The synthetic route of 2401-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoroaniline

[446] 2-chloro-4-fluoroaniline (1 g, 7 mmol) was added to concentrated sulfuric acid (15 mL) at Q0 C, followed by the addition of guanidine nitrate (875 mg, 7 mmol). The mixture was warmed to it and stirred for 2 h. Subsequently, the mixture was poured onto ice and neutralized with aqueous sodium hydroxide (4N) until the pH was 9. The mixture was diluted with EtOAc and water, the organic phase was isolated and the aqueous phase was extracted with additional EtOAc (2x). The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (0% – 10% EtOAc/heptane) to afford 2-chloro- 4-fluoro-5-nitroaniline (A2) as light brown solid.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; HUANG, Wei-Sheng; LI, Feng; DALGARNO, David, C.; GONG, Yongjin; ISHCHENKO, Alexey, V.; KOHLMANN, Anna; SHAKESPEARE, William, C.; WEST, Angela, V.; XU, Yongjin; YOUNGSAYE, Willmen; ZHANG, Yun; ZHOU, Tianjun; ZHU, Xiaotian; (444 pag.)WO2015/175632; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 108-37-2,Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, 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.

Under similar experimental conditions and reagent amounts in 2.2., the mixture was dissolved in 0.02 mL of IL and 1 mL of DMF. The organic phase was passed through silica gel in order to retain the IL and analyzed by GC and the isolated products characterized by 1H NMR, GC-MS, IR, and mp.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chlorobenzene, its application will become more common.

Reference:
Article; Cardenas, Juan C.; Fadini, Luca; Sierra, Cesar A.; Tetrahedron Letters; vol. 51; 52; (2010); p. 6867 – 6870;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 108-37-2,Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, 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 2-bromo-6-chlorobenzaldehyde (i-5b). To a solution of l-bromo-3-chlorobenzene (i-5a) (5 g, 26. mmol) in THF (50 mL) was added LDA (1 M, 31.3 mL, 8.7 mmol) dropwise via an addition funnel at -70 C. The mixture was stirred at -70 C for 1 h. DMF (2.87 mL, 39.1 mmol, 227 mmol) in THF (20 mL) was added dropwise maintaining the internal temperature below -70 C. The reaction was stirred vigorously at -70 C for 1 h. Warmed to -30 C, the reaction was poured into 1 M HCl (100 mL) partitioned between water (10 mL) and DCM (30 mL). The aqueous layer was extracted with DCM (20 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to afford the title compound (3.6 g, yield: 59 %). LCMS (ESI) calc’d for C7H4BrC10 [M+H]+: 219, found: 219.

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28591; (2014); A2;,
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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

To a mixture of tert-butyl (S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (149 mg, 344 mumol) and 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (48 mg, 286.40 mumol) in t-AmOH (3 mL) was added 2.0M t-BuONa in THF (286 muL, 572 mumol) and tBuXPhos-Pd-G3 (23 mg, 29 mumol) and the resulting mixture was heated to 100 C. for 15 h. The reaction mixture was cooled to rt and then concentrated in vacuo to give a (S)-tert-butyl 4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=566.5 (M+H)+, which was used without further purification. Of the butanoate intermediate, 80 mg, 141 mumol, was taken up in DCM (1 mL) and TFA (400 muL) and the resulting mixture was stirred at rt for 6 h and then concentrated in vacuo. The crude residue was purified by chiral SFC to give a first fraction containing the title compound. LCMS (ESI+): m/z=510.3 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.18 (s, 1H) 7.19 (d, J=7.28 Hz, 1H) 7.08 (d, J=3.53 Hz, 1H) 6.59 (d, J=3.53 Hz, 1H) 6.40 (d, J=7.28 Hz, 1H) 4.61 (t, J=6.17 Hz, 1H) 3.76 (s, 4H) 3.34-3.40 (m, 3H) 3.33 (s, 3H) 3.22-3.29 (m, 1H) 2.99-3.19 (m, 4H) 2.69 (t, J=6.17 Hz, 2H) 2.58 (br s, 2H) 2.32-2.43 (m, 1H) 2.11-2.21 (m, 1H) 1.86 (dt, J=11.52, 6.04 Hz, 2H) 1.74 (br s, 4H) 1.16 (d, J=5.95 Hz, 3H).

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; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics