Category: chlorides-buliding-blocks

Reference of 39191-07-6, 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. 39191-07-6 name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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.

Diisopropylethylamine (0.07 mL, 0.40 mmol) was added to a mixture of 4-chloro-3-[(7-oxo-2-piperidin-1-yl-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-benzoic acid (0.05 g, 0.11 mmol) (from Example 61 supra) and HATU (0.076 g, 0.20 mmol) in DMF (2.0 mL). The resulting mixture was stirred at room temperature for 30 minutes. 3-Chloro-N-methylbenzylamine (Aldrich) (0.06 mL, 0.40 mmol) was added. The mixture was stirred for 18 hours and then partitioned between ethyl acetate and water. The precipitate was collected by filtration and washed with methanol and dried in vacuum oven to give 7-oxo-2-piperidin-1-yl-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid {2-chloro-5-[(3-chloro-benzyl)-methyl-carbamoyl]-phenyl}-amide. (Yield 0.040 g, 62.5%).HR-MS (ES+) m/z Calculated for C28H27Cl2N6O3 ([M+H]+): 587.1335. Found: 587.1340.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Chlorophenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 26487-67-2, 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 26487-67-2 as follows.

1-(2-Chloroethyl)azepane hydrochloride (514 mg, 2.59 mmol), 50percent NaOH (10.4 mL,12.97 mmol), and a catalytic amount of benzyltriethylammonium chloride were added to a solution of (2-phenylimidazo[2, 1 -b][1 ,3,4]thiadiazol-6-yl)methanol (120 mg, 0.52 mmol) in toluene (3 mL) under argon atmosphere. The resulting mixture was refluxed for 6 h. The reaction mixture was diluted with water and extracted withEtOAc. The organic extracts were dried with Na2504 and evaporated to dryness. The crude product was purified by silica gel column chromatography (EtOAc:MeOH mixtures of increasing polarity as eluent) to afford the desired product (393 mg, 67percent). The product was converted into the corresponding maleate salt by adding maleic acid (27 mg, 0.23 mmol) in acetone (0.25 mL), followed by filtration of the resulting solid and drying under vacuum.1H-NMR (DMSO-d6, 300 MHz) & 9.24 (s, 1H), 8.27 (s, 1H), 7.94 (m, 2H), 7.62 (m,3H), 6.00 (s, 2H), 4.55 (s, 2H), 3.78 (t, J= 5.1 Hz, 2H), 3.31 (m, 6H), 1.76 (m, 4H),1.59(m, 4H)ppm.ESI(+)-HRMS: 357.1746 [M+H].

According to the analysis of related databases, 26487-67-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; ALCALDE-PAIS, Maria de las Ermitas; DIAZ-FERNANDEZ, Jose-Luis; MESQUIDA-ESTEVEZ, Maria, de les Neus; PALOMA-ROMEU, Laura; WO2014/6130; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. category: chlorides-buliding-blocks

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 16799-05-6, name is 3-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Chlorophenethyl Bromide

The starting material can be manufactured, for example, as follows: 50 ml of ethanol, 50 g of potassium hydroxide and 8.8 ml of water are added to 39.8 g of 1-ethoxycarbonyl-4-[2-(3-chlorophenyl)-ethyl]-piperazine, obtainable by reacting 17.7 g of 1-ethoxycarbonylpiperazine and 24.6 g of 2-(3-chlorophenyl)-ethyl bromide while heating at 120-125 under nitrogen, and the whole is heated under reflux for 3 hours. The whole is then allowed to cool, is diluted with 300 ml of water and 300 ml of toluene and shaken thoroughly, and then the organic phase is separated off, washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. 1-[2-(3-chlorophenyl)-ethyl]piperazine is obtained and can be purified via the hydrochloride (m.p. 260) from which it can then be freed again by treatment with sodium hydroxide solution, separation with diethyl ether and evaporation of the latter.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16799-05-6.

Reference:
Patent; Ciba-Geigy Corporation; US4804661; (1989); A;,
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. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3Cl2F

5.Og (30mmol) of 2, 4-dichloro-l-fluorobenzene was stirred in 40 ml of concentrated sulfuric acid under ice cooling, and 3.1g (30 mmol) of potassium nitrate was added to this stirring solution. The temperature was returned to room temperature, and the mixture was stirred for 12 hours, then, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, then, dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.2 g (yield: 97%) of the aimed compound.

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2007/131680; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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. HPLC of Formula: C3H7ClO

4-( 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 00 mg, 0.52mmol), 1-chloro-2-methoxyethane (0.056 mL, 0.62 mmol) and cesium carbonate (252mg, 0.73 mmol) in DMF (1 mL) were heated in microwave reactor at 160 C for 30 min.The reaction mixture was concentrated under reduced pressure and purified by silica gelchromatography (ISCO, hexanes/ethyl acetate 0-100% over 15 min) to isolate CompoundB162a (130 mg, 100% yield). HPLC: RT = 1.0 min (LCMS Method M). MS (ES): m/z= 253.0 [M+H( 1H NMR (500MHz, CHLOROFORM-d) 8 8.04 (s, 1H), 7.83 (d,J=18.4 Hz, 1H), 4.37 (t, J=5.2 Hz, 1H), 3.78 (t, J=5.2 Hz, 1H), 3.38-3.31 (m, 2H), 2.98(s, 3H), 2.90 (s, 3H), 1.34 (s, 6H), 1.26 (s, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FINLAY, Heather; JIANG, Ji; KIM, Soong-Hoon; PARKHURST, Brandon; QIAO, Jennifer X.; WANG, Tammy C.; PI, Zulan; TORA, George O.; LLOYD, John; JOHNSON, James A.; WO2014/15088; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 53531-69-4, 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 53531-69-4 as follows.

To a stirred mixture of potassium carbonate (74.8 g, 0.542 mol) in DCM (7OmL) andH20 (220 mL) at -10C was added pyrrolidine (21.2 g, 0.298 mol) in portions, and theresulting mixture was stirred for 20 mm. Then (4-bromophenyl)methanesulfonyl chloride (73.0 g,0.27 1 mol) in DCM (400 mL)was added drop-wise. The resultant mixture was stirred for lh at RT. The organic phase was separated, washed with H20, brine, dried over Na2SO4, and concentrated. The residue was recrystallized from 5% EtOAc/petroleum ether to give compound1-74. ?H NMR (300 MHz, CDC13) oe: 7.52 (d, 2H), 7.25 (d, 2H), 4.20 (s,2H), 3.20-3.30 (m, 4H),1.80-1.92 (m, 4H); LRMS found: 328 [M+23].

According to the analysis of related databases, 53531-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew L.; DINSMORE, Christopher; FULLER, Peter H.; GUERIN, David J.; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; KONG, Norman; LIU, Yumei; WO2014/146246; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. HPLC of Formula: C6H3BrClN3

EXAMPLE 41 1 -(4- { 3 – IY 1 S)- 1 -( 6-Chloroimidazo Gamma 1 ,2-blpyridazin-8-ylamino ethyl1 -7-fluoro-8-methyl- quinolin-2-yl)piperazin-l-yl)ethanoneIntermediate 21 (800 mg, 2.42 mmol) and 8-bromo-6-chloroimidazo[l,2- >]- pyridazine (670 mg, 2.8 mmol) in NMP (8 mL) were treated with DIPEA (1.4 g, 11 mmol) and heated at 120C under microwave irradiation for 1 h. The reaction mixture was partitioned between water (25 mL) and EtOAc (150 mL). The organic layer was washed with water (25 mL) and brine (25 mL), then dried (phase separation cartridge) and concentrated in vacuo. Purification by column chromatography (Si02, 20% EtOAc in isohexane) gave the title compound (400 mg, 38%) as a white solid, delta? (CDC13) 8.13 (IH, s), 7.69 (IH, s), 7.52 (IH, dd, J8.92, 6.04 Hz), 7.46 (IH, s), 7.17 (IH, t, J9.01 Hz), 6.48 (IH, d, J6.64 Hz), 6.28 (IH, s), 5.08-5.00 (IH, m), 4.10-4.02 (IH, m), 3.95-3.70 (3H, m), 3.46-3.18 (4H, m), 2.61 (3H, d, J2.34 Hz), 2.21 (3H, s), 1.83 (3H, d, J6.80 Hz). LCMS (ES+) 482/484 (M+H)+, RT 4.22 minutes {Method 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 933190-51-3, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2011/58109; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 6276-54-6,Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8- tetrahydropyrimido[4,5-(i]pyrimidin-4-yl]-4-methyl-N-propylbenzamide (206 mg, 0.4 mmol) in DMF (4 mL) was added (3-chloropropyl)amine hydrochloride (78 mg, 0.6 mmol) and triethylamine (112 uL, 0.8 mmol). The mixture was heated with microwave at 600C for 2 hrs. The mixture was separated by flash chromatography to afford the title compound (100 mg, 47%).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/147109; (2007); 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(2-Chloroethyl)azepane hydrochloride

A solution of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-ol (66 mg, 0.477 mmol), potassium carbonate (264 mg, 1.91 mmol), 2-(hexamethylenimino)ethyl chloride hydrochloride (142 mg, 0.717 mmol) and Nal (catalytic amount) in 3 mL of DMF, was heated to 90 ºC under nitrogen for 18 h. The mixture was allowed to cool to room temperature and evaporated to dryness. The residue was partitioned between water and EtOAc, the organic layer washed with water, dried and concentrated under vacuum to afford a residue of 101 mg that was purified by flash chromatography on silica gel with EtOAc/MeOH eluent mixtures from 90:10 to 60: 40 with 1percent TEA to give 58 mg (46percent) of yellow oil.

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics