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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7ClFN

The compound of intermediate 2 (122 mg, 535 mumomicronIota) was provided in DMF (1.5 mL). N,N-diisopropylethylamine (280 mu, 1.6 mmol), propane phosphonic acid anhydride (T3P, 470 mu, 50% in DMF, 800 mumomicronIota) and 1-(3-chloro-5-fluorophenyl)methanamine (128 mg, 802 mumomicronIota) were added, and the mixture was stirred at room temperature for 4 days. After concentration, the remaining material was triturated with ethanol and water and the mixture was stirred for 15 minutes. The precipitate was collected by filtration, and was dried under reduced pressure. 156 mg (76% of theory) of the title compound were obtained. LC-MS (method 2): Rt = 1.12 min; MS (ESIpos): m/z = 370 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 2.323 (0.77), 2.327 (1.12), 2.332 (0.77), 2.523 (2.87), 2.665 (0.83), 2.669 (1.10), 2.674 (0.79), 2.729 (1.58), 2.889 (2.01), 4.481 (9.75), 4.496 (9.57), 7.167 (2.39), 7.174 (3.41), 7.177 (2.74), 7.191 (2.58), 7.195 (3.49), 7.198 (3.56), 7.201 (3.44), 7.205 (1.69), 7.219 (5.21), 7.224 (8.57), 7.233 (8.41), 7.242 (9.14), 7.247 (5.78), 7.260 (2.05), 7.272 (4.61), 7.277 (8.15), 7.280 (5.04), 7.313 (2.86), 7.318 (4.09), 7.324 (2.31), 7.335 (2.91), 7.341 (4.03), 7.346 (2.29), 7.457 (0.65), 7.466 (4.06), 7.470 (3.35), 7.476 (2.58), 7.483 (3.11), 7.489 (3.27), 7.500 (0.48), 7.597 (0.57), 7.607 (3.75), 7.613 (3.15), 7.620 (2.44), 7.626 (2.94), 7.630 (3.32), 7.638 (0.53), 7.823 (0.57), 8.306 (16.00), 8.986 (2.34), 9.001 (4.83), 9.015 (2.25), 9.138 (15.50), 13.287 (5.95).

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; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; ZORN, Ludwig; STEIGEMANN, Patrick; GRUeNEWALD, Sylvia; ALGIRE, Carolyn; NEUHAUS, Roland; CHRISTIAN, Sven; GUeNTHER, Judith; KOPPITZ, Marcus; SCHWEDE, Wolfgang; (78 pag.)WO2016/202756; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 90390-33-3,Some common heterocyclic compound, 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, molecular formula is C7H7ClFN, 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.

3.2 1 -l3enzyl-3-hydroxypyrrolidine-3-carboxylic acid (100mg) and 3-chloro-5-fluorobenzylamine (79 mg) are dissolved in one millilitre of dried DM50 and cooled to 0C. o-(7-Azabenzotrial-l -yl)-N,N,N?,N?-tetramethyluroniumhexafluorophosphate (206 mg) and 4-methylmorpholine (0.124 ml) are then added. The batch is stirred at 25 C. for 2 hours and then immediately purified by chromatography, giving N-(3-chloro-5-fluorobenzyl)-l -benzyl-3-hydroxypyrro- lidine-3-carboxamide (37 mg) as colourless amorphous solid.

The synthetic route of 90390-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4261-67-0, 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. 4261-67-0 name is 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, 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 3 Cis(+)-3-acetyloxy-2,3-dihydro-5-(2-methyl-3-dimethylaminopropyl)-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one oxalate (diastereoisomer B) 5 g cis(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one, 2.9 g 2-methyl-3-dimethylaminopropylchloride hydrochloride, 5.7 g K2 CO3, 1.4 ml H2 O were reacted in 75 ml acetone, according to the procedure as in Example 1 (a), then reacted with 70 ml acetic anhydride, (see Example 1 (b)). The crude was treated with ethyl ether and the so obtained solid is filtered off and the solution was evaporated to dryness. This procedure was repeated. 4.3 g residue were dissolved in isopropyl alcohol and treated with 1.2 g oxalic acid. A solid, which was crystallized from acetone-ethyl ether, was obtained; m.p. 84¡ã-89¡ã C.; [alpha]D20 =119.3 (H2 O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Istituto Luso Farmaco d’Italia S.p.A.; US5571807; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924818-16-6, name is (5-Chloro-2,4-difluorophenyl)methanamine, 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 924818-16-6, Product Details of 924818-16-6

N-(5-Chloro-2,4-difluorobenzyl)-2,2-dimethoxyacetamide; A mixture of methyl dimethoxyacetate (1.45 g, 10.7 mmol) and 5-chloro-2,4-difluorobenzylamine (1.78 g, 10.0 mmol) in a sealed tube was heated at 80¡ã C. for 20 h. After that time, the mixture was diluted with EtOAc (20 ml), washed with HCl (2 N, 10 ml), saturated Na2CO3 (10 ml), H2O (10 ml) and brine (10 ml), and dried over MgSO4. After concentrated in vacuo, the title compound was obtained as a brown oil. 1H NMR (400 MHz, CDCl3): delta=3.41 (s, 6 H), 4.46 (d, J=6.4 Hz, 2H), 4.74 (s, 1H), 6.92 (t, J=8.8 Hz, 1H), 6.93 (brs, 1H), 7.41 (t, J=8.0 Hz, 1H). MS(ES+): m/z=280.03/282.01 (95/57) [MH+]. HPLC: tR=3.02 min (polar-5 min, ZQ3).

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; OSI Pharmaceuticals, Inc.; US2009/197862; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 621-62-5, 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. 621-62-5 name is 2-Chloro-1,1-diethoxyethane, 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.

0.95 g (2.5 mmol) of 5-chloro-7-(1,2-dimethylpropylamino)-6-(3-methylthiophen-2-yl)pyrazolo-[1,5-alpha]pyrimidine-3-carboxamide was dissolved in 25 ml of ethanol, and 1.0 g (6.5 mmol) of chloroacetaldehyde diethyl acetal was added. The mixture was stirred for 3 hours at 120 C. and 15 bar in a microwave oven (200 W). The reaction mixture was then concentrated under reduced pressure, and the residue that remained was chromatographed on silica gel using a mixture of cyclohexane:ethyl acetate=1:1. This gave 0.3 g of [5-chloro-6-(3-methylthiophen-2-yl)-3-oxazol-2-yl-pyrazolo[1,5-alpha]pyrimidin-7-yl](1,2-dimethylpropyl)amine (logPs=4.3; content according to HPLC: 98%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1,1-diethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; Gebauer, Olaf; Gayer, Herbert; Heinemann, Ulrich; Herrmann, Stefan; Hillebrand, Stefan; Elbe, Hans-Ludwig; Ebbert, Ronald; Wachendorff-Neumann, Ulrike; Dahmen, Peter; Kuck, Karl-Heinz; US2005/187224; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33050-36-1, These common heterocyclic compound, 33050-36-1, name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, 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 101-(2-Morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]ureaa) The 1-(2-morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]urea can be prepared in the following way:277 mg of n-tributyl phosphine are added to a solution of 462 mg of 1-(2-morpholin-4-ylethyl)-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea in 5.5 cm3 of tetrahydrofuran. This mixture is stirred for 1 h at 20 C. with nitrogen sparging, before the addition of 176 mg of 3-chloro-1,2,4-triazolo[4,3-b]pyridazine, 166 mg of potassium tert-butoxide, 12 mg of tetraphenyldiphosphoxane and 11 cm3 of toluene and stirring for 30 min at 20 C. with nitrogen sparging. 10 mg of tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium(0) are then added to the resulting mixture and the subsequent mixture is brought to reflux for 17 h. The solvent is concentrated under reduced pressure and the residue is then taken up in water and 0.1N hydrochloric acid HCl. The mixture obtained is then extracted with a 90/10 mixture of ethyl acetate/methanol. 632 mg of a yellow oil are obtained, and chromatographed on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 muM), elution being carried out with a gradient of dichloromethane then dichloromethane/methanol: 99/1, 98/2, 97/3, 96/4, 95/6, 92/8, 90/10, 80/20. 75 mg of 1-(2-morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]urea are thus obtained in the form of a beige powder, the characteristics of which are as follows:MELTING POINT: 252 C. (Koefler block)NMR SPECTRUM 1H NMR (400 MHz, d6-DMSO) deltappm: 2.36-2.45 (m, 6H) 3.24-3.36 (m, 2H) 3.55-3.63 (m, 1H)6.78 (br. s., 0H) 7.38-7.48 (m, 0H) 7.57 (d, J=8.5 Hz, 0H) 8.04 (d, J=1.5 Hz, 0H) 8.43 (dd, J=9.5,1.5 Hz, 0H) 8.70 (dd, J=4.5, 1.5 Hz, 0H) 10.85-10.95 (m, 0H)MASS SPECTRUM: UPLC-MS-DAD-ELSD: 457(+)=(M+H)(+).

Statistics shows that 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 33050-36-1.

Reference:
Patent; sanofi-aventis; US2010/298315; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 320-51-4, These common heterocyclic compound, 320-51-4, name is 4-Chloro-3-(trifluoromethyl)aniline, 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 S 1-Chloro-4-fluoro-2-(trifluoromethyl)benzene 4-Chloro-3-(trifluoromethyl)benzenamine (19.5 g, 100 mmoles), water (40 ml) and c.hydrochloric acid (40 ml) were heated with stirring on a steam bath until a white solid formed. The mixture was cooled (ice-salt bath) and a solution of sodium nitrite (7 g, 101 mmoles) in water (15 ml) was added over 15 mins. After stirring for a further hour at 0, tetrafluoroboric acid (30 g of 40% aqueous solution) was added dropwise over 15 minutes. After one hour the solid was filtered off, washed with water (10 ml), methanol (30 ml) and ether (30 ml) and then dried in vacuo. The dry compound was heated at 140-180 until no more fumes were observed. The cooled residue was dissolved in ethyl acetate, washed with 5% aqueous sodium hydroxide, dried Na2 SO4) and the solvent was removed in vacuo. The residue was distilled in vacuo (12 mmHg, oven temperature 50-55) to give the sub-title compound as a colourless oil (7.5 g). M+ 200/198; nmr (CDCl3)delta7.8-7.2 (m).

The synthetic route of 320-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fisons plc; US4607041; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 54730-35-7, The chemical industry reduces the impact on the environment during synthesis 54730-35-7, name is 3,5-Dichloro-4-methylaniline, I believe this compound will play a more active role in future production and life.

To a solution of HBr (40% in water, 3.4 mL) in water (3 mL) was added 3,5-dichloro-4-methylaniline (2.0 g, 11.4 mmol). The suspension was heated to dissolve as much of the solid as possible, then the mixture was cooled to 0 degrees C. and a solution of sodium nitrite (0.83 g, 12.0 mmol) in water (2 mL) was added dropwise (temperature was maintained <5 degrees C.). After 10 min., the diazonium salt mixture was poured into a mixture of CuBr (8.2 g, 57.0 mmol) in 40% aq. HBr (13 mL) at room temperature. The resulting mixture was heated at 50 degrees C. for 45 min., then cooled to room temperature. The mixture was diluted with water and extracted with dichloromethane (3¡Á). The combined organics were filtered through Celite and dried over sodium sulfate, then concentrated in vacuo to provide the product, 5-bromo-1,3-dichloro-2-methylbenzene, as an orange solid. 1H NMR (400 MHz, CDCl3) delta 2.40 (s, 3H), 7.43 (s, 2H). 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, 3,5-Dichloro-4-methylaniline, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

54730-35-7, name is 3,5-Dichloro-4-methylaniline, 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. category: chlorides-buliding-blocks

Transferred 3,5-dichloro-4-methylaniline (0.28 g, 1.59 mmol, Eq: 1.00) to a 50-mL round-bottomed flask using dichoromethane (10 mL). Added Iota,Gamma-thiocarbonyldiimidazole (429 mg, 2.41 mmol, Eq: 1.51) and stirred overnight at room temperature. HPLC showed no starting material remaining. Concentrated the reaction mixture onto silica. Purified using a 12 g silica column on an Intelliflash 280; collected peaks only in 9 mL fraction at 32 mL/min; equilibrated with heptane; dry loaded; eluted 1 min with heptane; increased from 0 – 10%> dichloromethane/heptane over 5 min. Obtained 226 mg (65%) of l,3-dichloro-5-isothiocyanato- 2-methylbenzene as a yellow solid.

The synthetic route of 54730-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); 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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4ClN3

Reference Example 11 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one [Show Image] Diethoxymethyl acetate (15 mL) was added to 2-chloropyridine-3,4-diamine (480 mg) and the resulting mixture was stirred at room temperature for 12 hours. To the mixture was added 1N hydrochloric acid and the precipitate formed was filtered, washed with diethyl ether and then dried to obtain a crude product (400 mg), 4-chloro-1H-imidazo[4,5-c]pyridine as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.45 (s, 1H), 8.51 (d, J = 5.9 Hz, 1H), 7.94 (d, J = 5.9 Hz, 1H). MS (ESI+) 154 (M+ +1, 100%). A hydrochloric acid/methanol solution (25 mL, methanol component 80-90%) was added to this solid (220 mg) and the resulting mixture was heated under reflux for 30 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and dried to obtain a crude product (150 mg), 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.40 (s, 1H), 7.58 (d, J = 7.2 Hz, 1H), 6.87 (d, J = 7.2 Hz, 1H). MS (ESI+) 136 (M++1, 100%). Under a nitrogen atmosphere, sodium hydride (134 mg, a 60% oil dispersion) was added to N,N-dimethylformamide (15 mL) and the resulting suspension was cooled to -15C. To the suspension was added 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (360 mg) and the resulting mixture was stirred at room temperature for 30 minutes. Then, chloro-2-(trimethylsilyl)ethoxymethane (0.550 mL) was added dropwise thereto, followed by stirring at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (developing solvent: chloroform/methanol = 20/1 to 10/1) to obtain 3-{[2-(trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (119 mg) and 1-{[2-(trimethyl-silyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (113 mg) each as a white solid. 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 11.49 (bs, 1H), 8.03 (s, 1H), 7.16 (m, 1H), 6.77 (d, J = 7.0 Hz, 1H), 5.91 (s, 2H), 3.66 (t, J = 8.2 Hz, 2H), 0.93 (t, J = 8.2 Hz, 2H), – 0.04 (s, 9H). MS (ESI+) 266 (M++1, 100%). 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 10.97 (bs, 1H), 7.84 (s, 1H), 7.21 (m, 1H), 6.56 (d, J = 7.1 Hz, 1H), 5.45 (s, 2H), 3.51 (t, J = 8.2Hz, 2H), 0.90 (t, J = 8.2 Hz, 2H), – 0.03 (s, 9H). MS (ESI+) 266 (M++1, 100%).

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 2770-01-6.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1690863; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics