Tag: M.W=100-200

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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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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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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Reference of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

General procedure: Distilled H2O in a three-necked roundbottom flask ispurged with nitrogen for 30 minutes. PdCl2 and KCl aresubsequently added to the flask and the solution is stirred atroom temperature for 1 h. Then, optionally substituted(R4)-allyl chloride is added and the resulting reactionmixture is stirred at room temperature overnight (18-20 irs).The reaction is extracted with chloroform, and the aqueouslayer washed with chloroform three times. The organiclayers are combined, dried over MgSO4, filtered and concentrated in vacuo. The crude product is recrystallised fromchloroform and methyl tert-butyl ether, and the resultingsolid is isolated by filtration and dried in vacuo; PdCl2 (590 mg, 3.33 mmol); KCl (473 mg, 6.67 mmol); cinnamyl chloride (1.39 mL, 9.99 mmol); H2O (83 mL). Thedimer is obtained as a yellow solid.

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

Reference:
Patent; Johnson Matthey Public Limited Company; Colacot, Thomas; Jon Deangelis, Andrew; (66 pag.)US9777030; (2017); B2;,
Chloride – Wikipedia,
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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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Chloro-2-methoxyaniline

Example 57; 4-(4-Chloro-2-methoxy-phenyl)-3-(4-ethoxy-phenyl)-5-methyl-4H-[1,2,4]triazole; The products of preparations 4 (1g, 4. 9mmol) and 91 (926mg, 5. 88mmol) were dissolved in xylene (20ml) and the reaction mixture was heated for 10 hours at 150C. Heating was continued for 4.5 hours with portions of para-toluenesulfonic acid (100mg) added to the mixture at regular intervals until tic analysis showed all of the starting material to be consumed. The reaction mixture was then taken up into 2N hydrochloric acid and ethyl acetate and partitioned. The aqueous layer was basified with sodium hydroxide pellets and re-extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate and evaporated to give a dark brown oil. Trituration with diethyl ether formed a dark brown solid that was re-crystallised from ethyl acetate to produce the title compound as a beige solid (340mg). Evaporation of the ethyl acetate gave a further residue that was purified by column chromatography on silica gel, eluting with dichloromethane : methanol : 0.88 ammonia, 98.2 : 0.2, to afford further amounts of product giving a total yield of 37% (629mg). ‘H NMR (CDCI3, 400MHz) d : 1.39 (t, 3H), 2.27 (s, 3H), 3.73 (s, 3H), 3.99 (q, 2H), 6.78 (d, 2H), 7.02-7. 06 (m, 3H), 7.31 (d, 2H). MS APCI+ m/z 344 [MH] +

According to the analysis of related databases, 93-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/82866; (2005); A2;,
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Synthetic Route of 13078-79-0, 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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (153 muL, 1.10 mmol) was added dropwise at 0 C to a stirred suspension of 2-(1H-indol-3-yl)-2-oxoacetyl chloride (5; 208 mg, 1.00 mmol) and 2-(3-chlorophenyl)ethylamine (139 muL, 1.00 mmol) in anhydrous tert-butyl methyl ether (20 mL). The reaction mixture was stirred at 0 C for 15 min and then for 1 h at room temperature, monitoring the reaction by TLC analysis. After completion of the reaction the mixture was washed with a saturated NaHCO3 aqueous solution and water (3 × 20 mL in each case). The organic layer was dried over anhydrous Na2SO4 and evaporated. Recrystallization of the crude product from ethanol 70% yielded colourless crystals (33%).Mp.: 184-186 C; IR (KBr): 3347 cm-1 and 3190 cm-1 (NH), 2938 cm-1 (CH aliph.), 1657 cm-1 (CO); 1H NMR (DMSO-d6, 400.1 MHz): delta (ppm) = 2.88 (t, 2H, J = 7.0 Hz, NHCH2CH2), 3.50 (dt, 2H, J = 6.4/6.8 Hz, NHCH2CH2), 7.21-7.34 (m, 6H, ar-H), 7.52-7.57 (m, 1H, ar-H), 8.21-8.27 (m, 1H, ar-H), 8.67 (s, 1H, ar-H), 8.81 (t, 1H, J = 5.8 Hz, NH), 12.24 (s, 1H, indole-NH); 13C NMR (DMSO-d6, 100.6 MHz): delta (ppm) = 34.2 (CH2), 39.2 (CH2); 112.5, 121.2, 122.5, 123.4, 126.1, 127.5, 128.5, 130.1, 138.4 (tert. C); 112.1, 132.9, 136.3, 141.9, 163.6, 182.1 (quat. C, one signal is missing due to peak overlap); C18H15ClN2O2 (326.78); calcd. C 66.16, H 4.63, N 8.57; found C 65.84, H 4.60, N 8.31; HPLC-purity: 99.3% at 254 nm and 98.9% at 280 nm, tN = 3.38 min, tM = 1.03 min (ACN/H2O; 55:45), lambdamax: 256 nm and 327 nm.

The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Schmidt, Stefanie; Preu, Lutz; Lemcke, Thomas; Totzke, Frank; Schaechtele, Christoph; Kubbutat, Michael H.G.; Kunick, Conrad; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2759 – 2769;,
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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. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5ClFN

To a solution of 4-chloro-3-fluoroaniline (15 g, 103.05 mmol) in dichloromethane (150 mL) was added ICl (25 g, 154.57 mmol) drop wise. The resulting black mixture was stirred at 24-29C for 2h. The mixture was diluted with 100 mL dichloromethane and washed with saturated solution of sodium bicarbonate (200 mL). The organic layer was concentrated to give the crude residue, which was purified by flash column chromatography on silica gel (0 to 0.5%ethyl acetate in Petroleum ether) to afford compound 41a (8 g brown solid and 12 g black solid, 71.5% yield in total). LCMS: R t = 0.974 min in 5-95AB_220&254 chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z = 271.8 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.53 (d, J = 8.0 Hz, 1H), 6.46 (d, J = 10.4 Hz, 1H), 4.12 (s, 2H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
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Synthetic Route of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

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-3-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
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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. 2401-24-3, name is 2-Chloro-5-methoxyaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8ClNO

Preparation of (2-Chloro-5-methoxy-phenyl)-urea (Intermediate 5) A solution of 2-chloro-5-methoxyaniline (5 g, 25.76 mmol) and potassium cyanate (5.22 g, 64.41 mmol) in a mixture of acetic acid (125 mL) and water (12.5 mL) was stirred at room temperature overnight. The solvent was evaporated, and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The layers were separated, the aqueous one being extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography on silica gel (cyclohexane/EtOAc/MeOH: 80/20/2) to give 2.06 g (40%) of intermediate 5. 1H NMR [(CD3)2SO] delta7.97 (br s, 1H, NH), 7.85 (d, J=3.0 Hz, 1H), 7.27 (d, J=9.0 Hz, 1H), 6.54 (dd, J=9.0, 3.0 Hz, 1H), 6.4-(br s, 2H), 3.71 (s, 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; Bernardelli, Patrick; Ducrot, Pierre; Lorthiois, Edwige; Vergne, Fabrice; US2002/198198; (2002); A1;,
Chloride – Wikipedia,
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Reference of 32768-54-0, These common heterocyclic compound, 32768-54-0, name is 2,3-Dichlorotoluene, 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.

General procedure: In a 1L reactor,add 61.5 g of 2,3-dichlorotoluene, 3.075 g of azobisisobutyronitrile (5%), 215.25 g of 2-dichloroethane, heat the mixture at 75 C and add 44 g of bromine drop wise,reflux reaction till red bromine fades , Intermittent drip and 136.2g27.5% hydrogen peroxide continues to react till red bromine no longer generates. Add a 49.2g30% aqueous solution of sodium carbonate to the reaction solution, reflux reaction for 8 h ,at the same time recover1,2-dichloroethane.

Statistics shows that 2,3-Dichlorotoluene is playing an increasingly important role. we look forward to future research findings about 32768-54-0.

Reference:
Patent; Lianyungang Industry Investment Group Co., Ltd.; Jiang Honglai; Jiang Xiao; Han Yong; Zang Han; Zhu Chengjie; Shen Weiwei; (5 pag.)CN107032968; (2017); A;,
Chloride – Wikipedia,
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