Month: June 2021

Related Products of 918538-05-3, 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.

To a solution of compound [1] (1g, 5.31 mmol, 1 eq) in ACN (10 ml) was added successively DIPEA (685 mg, 5.31 mmol, 1 eq) and morpholine (462 mg, 5.31 mmol, 1 eq). The reaction mass was stirred at room temperature for 1 hr. Excess of solvent was evaporated to obtain a yellow solid. Purification of solid residue was done by column chromatography with silica gel (100: 200 mesh) in solvent system 10 % EtOAc in cyclohexane to get compound [2] as an off-white solid (1.1 g, 87%).1H NMR (CDCl3, 300 MHz): d ppm 7.58 (1H,d), 6.74 (1H, dd, J= 4.5,1.2 Hz),6.63 (1H, m), 4.05 (4H, t, J= 4.8Hz), 3.85 (4H, t, J= 4.8 Hz); ESIMS: 238 (M+ + 1).

Statistics shows that 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine is playing an increasingly important role. we look forward to future research findings about 918538-05-3.

Reference:
Article; Dugar, Sundeep; Hollinger, Frank P.; Kuila, Bilash; Arora, Reena; Sen, Somdutta; Mahajan, Dinesh; Bioorganic and Medicinal Chemistry Letters; vol. 25; 16; (2015); p. 3142 – 3146;,
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These common heterocyclic compound, 6306-61-2, name is N-(2-Chloroethyl)propan-2-amine hydrochloride, 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. Formula: C5H13Cl2N

In anhydrous conditions under argon atmosphere, NaH (60% in mineral oil, 0.232 g, 5.8 mmol) was added slowly to a suspension of intermediate 9 (0.35 g, 0.97 mmol) in N,N- dimethylformamide (10 ml) at 0C and the mixture was stirred at 0C for 10 minutes. Isopropylaminoethyl chloride hydrochloride (0.459 g, 2.9 mmol) was added portionwise and the reaction mixture was stirred at room temperature for 48 h ours. The reaction mixture was quenched with a saturated solution of ammonium chloride (15 ml) and the mixture was extracted with ethyl acetate (3 x 50 ml). The combined organic layers were washed with a saturated solution of sodium chloride (2 x 50 ml), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified bychromatography over silica gel (mobile phase, gradient from 95% DCM, 5%MeOH to 90% DCM, 10%). The fractions were collected and the solvent was evaporated yielding 0.22g of fraction 2 composed of a mixture of compound 4 and compound 6..Fraction 1 and Fraction 2 were combined and purified by achiral SFC (mobile phase, 0.3% isopropylamine, 86% C02, 14% MeOH). The desired fractions were collected and concentrated, yielding 17 mg of compound 5, 168 mg of compound 4 and 60 mg of product fraction 3 containing compound 4 and compound 6..Compound 4 was converted into the HCI salt (3eq. 1 M solution in water) in Et20 and triturated . The precipitate was filtered off, washed with Et20 and dried under vacuum, yielding 153 mg of compound 4 (mp = 175C Kofler).Product fraction 3 was purified by chiral SFC on (5muiotaeta mobile phase, 0.3%isopropylamine, 85% C02, 15% MeOH), yielding 22mg of compound 6.

The synthetic route of N-(2-Chloroethyl)propan-2-amine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; OBRINGER, Michel; MARIN, Julien Jeremie Joseph; JEANTY, Matthieu; WO2013/61077; (2013); 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. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39065-95-7

To a solution of (R)-7-bromo-2-(difluoromethyl)-1-(1-hydroxypropan-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid (5c, 100 mg, 0.286 mmol, 1 eq) and 4-(chlorodifluoromethoxy)aniline (1h, 66.54 mg, 0.344 mmol, 1.2 eq) in DMF (2 mL) was added HATU (130.69 mg, 0.344 mmol, 1.2 eq) and DIEA (148.08 mg, 1.15 mmol, 199.56 uL, 4 eq). The mixture was stirred at 15 C. for 12 hr. LCMS showed 5c was consumed completely and desired MS was detected. The mixture was diluted with water (5 mL) and extracted with EtOAc (10 mL*3). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to afford 5e as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 10.56 (s, 1H), 8.49 (s, 1H), 8.21 (s, 1H), 7.93 (d, J=9.3 Hz, 2H), 7.43-7.71 (m, 1H), 7.38 (br d, J=9.0 Hz, 2H), 6.02 (br d, J=6.2 Hz, 1H), 5.23-5.45 (m, 1H), 3.72-3.93 (m, 2H), 1.60 (br d, J=6.8 Hz, 3H).

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 39065-95-7.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
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Reference of 33863-76-2, A common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Preparation 32 1-Bromo-3-chloro-5-methoxybenzene Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2*20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluding with cyclohexane to provide the title compound (302 mg) as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.77 (s, 3H), 6.82 (s, 1H), 6.94 (s, 1H), 7.09 (s, 1H). Microanalysis: Found: C, 37.94; H, 2.75. C7H6BrClO requires C, 37.96; H, 2.73%.

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
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4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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. COA of Formula: C5H10ClO3P

In a reflux condenser, thermometer, stirrer,Constant pressure dropping funnel 2000mL four-necked flask was added 74g of cyclic phosphorus oxychloride,8 g of anhydrous aluminum trichloride and 800 mL of toluene were added to dissolve them with stirring.Under stirring at 10 C,22.8gBetween cyclohexane diamine four-necked flask,After the addition of cyclohexane diamine is completed,The temperature was raised to 80 C,And the reaction at this temperature 6h, after the reaction was recovered by vacuum distillation solvent,The residue was washed three times with deionized water to give a white solid powder,After drying at 60 C for 10 h, 73.3 g of a product was obtained in a yield of 89.8% by weight.

The synthetic route of 4090-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sinopec Corporation; Sinopec Corporation Fushun Petrochemical Institute; Zhao Wei; Wang Xiaolin; Li Ming; Liu Mingrui; Xue Qian; (8 pag.)CN104558039; (2017); B;,
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Reference of 29882-07-3, These common heterocyclic compound, 29882-07-3, name is 4-Chloro-1,1-dimethoxybutane, 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.

2. 2-(5-Cyanomethyl-1H-indol-3-yl)ethylamine. Hydrochloride 4-Chlorobutanal dimethylacetal (37.07 g, 0.24 mol) was added to a stirred solution of 4-hydrazinobenzyl cyanide hydrochloride (47.0 g, 0.26 mol) in EtOH/H2 O (5:1; 21) and refluxed for 4.5 h. The reaction mixture was evaporated to dryness under vacuum, MeOH (150 ml) added, and the mixture left at 0° C. for 10 h. The resultant pale yellow precipitate was filtered under vacuum, washed with Et2 O/MeOH (5:1; 2*100 ml) and dried. The product was used without further purification (24.1 g, 40percent), m.p. 239°-241° C.; Rf 0.4 in CH2 Cl2 /EtOH/NH3 (40:8:1); 1 H NMR (360 MHz, D2 O) 3.18 (2H, t, J=7.1 Hz, CH2); 3.36 (2H, t, J=7.1 Hz, CH2); 4.02 (2H, s, CH2); 7.22 (1H, dd, J=1.5and 8.4 Hz, Ar-H); 7.36 (1H, s, Ar-H); 7.56 (1H, d, J=8.4 Hz, Ar-H); 7.66 (1H, s, Ar-H).

Statistics shows that 4-Chloro-1,1-dimethoxybutane is playing an increasingly important role. we look forward to future research findings about 29882-07-3.

Reference:
Patent; Merck Sharp & Dohme Limited; US5298520; (1994); A;,
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Related Products of 2533-69-9,Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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 solution of 3-bromo-4-chlorobenzene-1,2-diamine (4 g, 18 mmol) in AcOH ( 30 mL) was added methyl 2,2,2-trichloroacetimidate (3.5 g, 20 mmol) drop wise at 0 C. Then the reaction mixture was stirred at room temperature overnight. The mixture was poured into water (200 mL), and precipitate was collected and dried to give 4-bromo-5-chloro-2-(trichloromethyl)-1H-benzo[djimidazole (5.5 g, 80%) as a white solid. HPLC/UV purity: 95%; LC-MS (ESI): 349.1 (M + 1).

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

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
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Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4.1.1 Ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate (6a) To a stirred solution of 3-fluoroaniline (1.11 g, 10.0 mmol) in CHCl3 (30.0 mL) was added dropwise N-chlorosuccinimide (NCS) in CHCl3 (20.0 mL) at 0 C. The mixture was stirred at 0 C for 42 h. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in Et2O. The mixture was washed with water, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel with EtOAc/n-hexane gave 4-chloro-3-fluoroaniline (259.4 g, 18% yield) as crystalline solids. To a stirred solution of the above aniline (259.4 mg, 1.78 mmol) in THF (8.9 mL) were added at 0 C ethyl chloroglyoxylate (237.3 muL, 2.14 mmol) and Et3N (296.6 muL, 2.14 mmol). The mixture was stirred at room temperature for 12 h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0 M HCl, saturated NaHCO3 and brine, then dried over MgSO4. Concentration under reduced pressure to provide the title compound 6a (435.2 mg, 99% yield) as brown crystals, which was used without further purification. 1H NMR (500 MHz, CDCl3) delta 1.44 (t, J = 7.50 Hz, 3H), 4.43 (q, J = 7.50 Hz, 2H), 7.24-7.25 (m, 1H), 7.35-7.40 (m, 1H), 7.70-7.75 (m, 1H), 8.93 (br, 1H); 13C NMR (125 MHz, CDCl3) delta 13.0, 64.1, 108.5 (d, J = 26.3 Hz), 115.9 (d, J = 3.75 Hz), 117.3 (d, J = 18.8 Hz), 130.9 (d, J = 10.0 Hz), 135.9, 153.9, 158.1 (d, J = 246.3 Hz), 160.5; HRMS (ESI), m/z calcd for C10H10ClFNO3 (MH-) 244.0182, found 244.0183.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Narumi, Tetsuo; Arai, Hiroshi; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Hirota, Yuki; Ohashi, Nami; Hashimoto, Chie; Nomura, Wataru; Matsushita, Shuzo; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 21; 9; (2013); p. 2518 – 2526;,
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Application of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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 suspension of sodium hydride (purity> 55%, 11.4 g) in N, N-dimethylformamide (150 mL),Under ice cooling, add 3-chloro-2-chloromethyl-1-propene (12.7 mL, CAS number: 1871-57-4),After stirring for 10 minutes at the same temperature,2- (tert-Butoxycarbonylamino) -1-ethanolA solution of (19.3 g, CAS number: 26690-80-2) in tetrahydrofuran (150 mL) was added dropwise over one and a half hours, and the mixture was stirred at room temperature for two and a half hours.The reaction solution was ice-cooled, water was added, and the mixture was extracted 3 times with diethyl ether,The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.After filtration and concentration under reduced pressure, the obtained residue is purified by silica gel column chromatography (n-hexane / ethyl acetate) to give the title compound.(16.0 g) was obtained as an oil.

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Healthcare Co Ltd; Naito, Hiroyuki; Suzuki, Takayuki; Murata, Takeshi; Kawai, Junya; Higuchi, Saito; (99 pag.)JP2020/45306; (2020); A;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

(iii) Preparation of N-[3-chIoro-4-[(3-fluorobenzyIoxy)phenyl]-6-iodo- quinazolin amine (3) Into a one liter four-necked round bottomed flask, 500mL of acetic acid, 50.0 g of N’- (2-cyano-4-iodo-phenyl)-N, N-dimethyl formamidine of the formula-(8) obtained according to the process given in the above step (ii) 51.0 g 3-chloro-4-(3′- fluorobenzyloxy)aniline were charged . The reaction mass was maintained at 115- 120 C for about 2 Hrs., the cooled to 25-35 C and quenched into ice cold water. The pH of the reaction mass was adjusted to basic by slow addition of aqueous ammonia solution and the reaction mass was filtered and dried at 70-75 C.Dry weight: 93.0 gPurity: 83.64% by HPLCThe purity of the product is enhanced by adopting the following procedure.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
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