Tag: M.W=100-200

Related Products of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a refluxing slurry of disodium carbonate (0.9 g. 0.01 mol) in 10 mL MeOH wasadded simultaneously a solution of 1,5-dichloropentan-3-one (0.93 mL, 0.01 mol) in 5 mL MeOH and a solution of 4-chloro-3-methylaniline (1 g, 0.01 mol) in 5 mL MeOH dropwise over 10 mins. The reaction was allowed to reflux for a further 2.5 h, then allowed to cool and concentrated, poured into water (10 mL), and extracted with DCM (2 x lOmL). The combined organics were dried over MgSO4 and concentrated to yield 1.38 g free flowing orange/brown oil. The crude product was purified using column chromatography (Biotage, 50 g SNAP KP-SIL, 10 -80percent EtOAc in heptane, 10 CV) to yield the title compound as a light yellow free-flowing liquid (890 mg, 86percent purity, 48percent).1H NMR (500 MHz, Chloroform-d) delta 7.22 (d, J = 8.7 Hz, 1 H), 6.83 (d, J = 2.9 Hz, 1H), 6.74 (dd, J = 8.7, 3.0 Hz, lH), 3.56 (t, J = 6.1 Hz, 4H), 2.55 (t, J = 6.1 Hz, 4H), 2.35 (s, 3H). LCMS Method D: rt 1.33 min, 91 percent; m/z 223.95 (MH+)

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

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
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Reference of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

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;,
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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. 348-59-4, name is 2,5-Dichlorofluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 348-59-4

[ETHYL 4-[(4-HYDROXY-1-PIPERIDINYL)METHYL]-?-PHENYL-1-PIPERIDINEACETATE ] (0.135 g) was dissolved in NMP (3 mL). 1, 4-Dichloro-2-fluorobenzene (0.2 mL) and potassium t- butoxide (56 mg) were added and the solution was heated to [50 C] for 40 h. The solution was cooled to ambient temperature and few drops of aqueous sodium hydroxide solution were added. The mixture was stirred for 60 h, then acetic acid (few drops) was added and the solvent was distilled. The residue was purified by HPLC (0.2% aqueous ammonia: acetonitrile; gradient 95: 5 to 50: 50) to give the title compound (21 mg). MS [[M+H] +] (ES+) 477/479 [IH] NMR [8 (CD30D)] 1.45 (1H, q), 1.68-1. 96 (9H, m), 2.16-2. 21 (2H, m), 2.25-2. 34 (2H, m), 2.57-2. 65 (3H, m), 2.80-2. 93 (2H, m), 4.29-4. 36 [(1H,] m), 4.38-4. 44 [(1H,] m), 6.83 [(1H,] dd), 7.02 (1H, d), 7.23 (1H, d), 7.32-7. 36 (3H, m), 7.44-7. 49 (2H, m)

The synthetic route of 348-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/29041; (2004); A1;,
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Synthetic Route of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-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.

To a suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (24.5 g, 125 mmol) in Et20 (300 ml) at -10 C under N2 was added TFAA (12.23 ml, 88 mmol) dropwise. The mixture was allowed to warm to rt for 18 h. The reaction mixturewas diluted with hexane (300 ml), and filtered. The filtrate was washed with ice-water,10% aq NaHCO3, and brine, dried over Na2SO4, and concentrated. A pale yellow solid obtained as N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96 % yield). MS (ESI) m/z: 242.1 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
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Reference 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;,
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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;,
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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. Recommanded Product: 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;,
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These common heterocyclic compound, 67952-93-6, name is 3-Chloro-4-methylbenzylamine, 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: C8H10ClN

General procedure: A mixture of 2-amino-3-nitrobenzoic acid (5.0 mmol), EDCI (6.0 mmol),and HOBt (0.6 mmol) in DCM (30 mL) was stirred at room temperature for 5 mins. Then, amines (6.0 mmol) were added and the reaction was stirred at room temperature overnight. After completion, the mixture was diluted with DCM, washed with water twice, dried over anhydrous Na2SO4, evaporated, and chromatographed (EtOAc – petroleum ether) to afford the compounds 2a-k.

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

Reference:
Article; Chen, Yinbo; Le, Vanminh; Xu, Xiaoyong; Shao, Xusheng; Liu, Jianwen; Li, Zhong; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3948 – 3951;,
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Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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

To stirred solution of pyridin-4-ylmethanamine (0.086 g, 0.798 mmol) in dioxane (5 mL) was dropwise added DIPEA (0.279 mL, 1.596 mmol) and stirred for 15 mm at room temperature. To the resulting reaction mixture was added 2,4-dichloropyrrolo[2,1- J][1,2,4]triazine (0.15 g, 0.798 mmol) stirred at room temperature for 1 h. The reactionwas monitored by LC-MS. The reaction mixture was concentrated under reduced pressure. To the residue was added water (50 mL) and extracted with ethyl acetate (3×80 mL). The combined organic phase was dried over anhydrous sodium sulfate filteredevaporated. The resulting crude product was purified by silica gel flash chromatography (ethyl acetate/petroleum ether) to get 2-chloro-N-(pyridin-4-ylmethyl)pyrrolo[2, 1-J][1,2,4]triazin-4-amine (0.14 g, 0.5 18 mmol, 64.9 % yield) as a brown solid. LCMS260.0 (M+H); rt 1.8 mm; Conditions E. ?HNMR: (300 MHz, DMSO-d6) oe 9.37-9.28 (m, 1H), 8.58-8.48 (m, 2H), 7.70 (dd, J2.6, 1.5 Hz, 1H), 7.38-7.30 (m, 2H), 7.03 (dd, J4.5, 1.5 Hz, 1H), 6.67 (dd, J4.2, 2.6 Hz, 1H), 4.75 (d, J6.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1939-99-7, name is Phenylmethanesulfonyl chloride, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1939-99-7, HPLC of Formula: C7H7ClO2S

K2CO3 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0 C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2SO4, filtered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200-300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound N-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) delta 7.40 (m, 5H), 4.58 (m, 1H), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Genentech, Inc.; Fauber, Benjamin; Gobbi, Alberto; Rene, Olivier; Bodil van Niel, Monique; Gancia, Emanuela; Gaines, Simon; Laddywahetty, Tammy; Vesey, David; Ward, Stuart; Winship, Paul; US2015/197529; (2015); A1;,
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