Tag: M.W=100-200

Electric Literature of 37045-73-1, These common heterocyclic compound, 37045-73-1, name is 3-(Methylsulfonamido)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.

Intermediate 6 (41 mg, 0.121 mmol), N-(3-amino-phenyl)-methane sulfonamide (68 mg, 0.365 mmol), glacial acetic acid (8 mul, 0.121 mmol) and n-butanol (1.3 ml) were combined and irradiated at 150 0C for 40 minutes in a Biotage 1-60 microwave reactor. The reaction mixture was evaporated and then purified by preparative LCMS (low pH buffer) to give a white solid (42 mg, 57%). 1H nuMR (400 MHz, DMSO-Cf6) delta ppm 0.53 – 0.61 (m, 2 H), 0.86 – 0.93 (m, 2 H), 1.49 – 1.57 (m, 1 H), 1.80 – 1.89 (m, 2 H), 3.00 (s, 3 H), 3.27 – 3.35 (m, 2 H), 3.53 – 3.61 (m, 2 H), 6.92 – 6.97 (m, 1 H), 7.13 (dd, 7=4.8, 3.9 Hz, 1 H), 7.27 – 7.34 (m, 1 H), 7.36 – 7.42 (m, 2 H), 7.58 (s, 1 H), 7.68 – 7.76 (m, 2 H), 8.46 – 8.60 (m, 2 H), 9.86 (s, 1 H), 10.20 (br. s, 1 H); m/z (ES+APCI)+: 487 [M+H]+.

The synthetic route of 37045-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL; WO2009/122180; (2009); A1;,
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4141-08-6, name is 2-Amino-N-methylbenzamide, belongs to amides-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. Computed Properties of C8H10N2O

Step 2: Preparation of 2-((2,5-dichloropyrimidin-4-yl)amino)-N-methylbenzamide (3); 2-Arrdno-N-iTiethylbenzarnide (2, 9 g, 60 mmol) and potassium carbonate ( 16.5 g, 120 mmol) were taken up in dimethylformamide (DMF )( 100 mL) to form a mixture and the mixture was stirred for 10 min. 2,4,5-trichloropyrimidine ( 1 1 g, 60 mmol) was added drop wise to the mixture and the mixture was stirred at 80 C for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled and filtered through a Buckner funnel. The filtered solid was washed with water and dried to afford 2-((2,5-dichloropyrimidin-4-yl)amino)-N-methylbenzamide as a light yellow solid (3, 15.2 g, 85.8%). NMR (DMSO-i/6): delta 8.90 (bs, 1 H), 8.60-8.40 (m, 1 H), 7.80-7.60 (d, 1 H), 7.70-7.50 (t, 1 H), 7.30-7.20 (t, 1 H), 2.80 (s, 3H).

The synthetic route of 4141-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GATEKEEPER PHARMACEUTICALS, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/140338; (2011); A1;,
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711007-44-2, name is 2,3-Diaminobenzamide, belongs to amides-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. Quality Control of 2,3-Diaminobenzamide

A mixture of 2,3-diamino-benzamide (1,51 g, 10.0 mmoles) or a 2, 3-DIAMINO- (N-SUBSTITUTED)-BENZAMIDE (10.0 mmoles) and a suitable paramagnetic aldehyde (of general formula V) or dia- magnetic aldehyde (of general formula VI) (10.0 mol), and toluene-p-sulphonic acid monohydrate (95 mg, 0.5 mmoles) is refluxed in toluene (40 mL) or in an other appropriate solvent till all the starting compounds are consumed (4-6 hours) under Dean and Stark apparatus. Then the solvent is evaporated in vacuo, the residue dissolved in CHC13 (50 mL) or in some other halogenated solvent, and an appropriate oxidant such as acti- vated Mn02 (4.30 g, 50.0 mmoles) is added and the mixture is stirred and refluxed for about 6 hours. The mixture was fil- tered through Cellite, evaporated and the residue was purified by flash column chromatography (CHCl3/Et2O or CHC13/MEOH) or crystallization to give compound la or Ib (yield: 39-73 %)

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HIDEG, Kalman; KALAI, Tamas; SUeMEGI, Balazs; WO2004/96793; (2004); A1;,
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Reference of 673-66-5, 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. 673-66-5, name is Azocan-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Dimethyl sulfate (1.42 mL, 15 mmol) and 2-azacyclooctanone (1.91 g, 15 mmol) were added to a dried, argon flushed 2-necked round bottomed flask and the mixture was heated at 60 0C for 23 h. The mixture was then cooled to r.t. and added to a saturated aq. solution of Na2CO3 (100 mL). This solution was extracted with ether, dried over Na2SO4, filtrated and evaporated to give a brownish oil of the title compound (1.71 g, 81%). 1H NMR (CDCl3) delta: 3.62 (s, 3H); 3.44-3.40 (m, 2H); 2.34-2.30 (m, 2H); 1-71-1.65 (m, 2H); 1.64-1.58 (m, 2H); 1.50-1.44 (m, 2H); 1.42-1.35 (m, 2H).

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

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; WO2008/64136; (2008); A2;,
Amide – Wikipedia,
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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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 16982-21-1

4-Chloromethyl-thiazole-2-carboxylic acid ethyl ester was prepared according to Summers, J. B., Jr. et al. (U.S. Pat. No. 5,486,525): A mixture of ethyl thiooxamate (7.0 g, 52.6 mmol) and 1,3-dichloroacetone (7.0 g, 55.1 mmol) in ethanol (300 mL) was heated at reflux overnight. The solvent was evaporated under reduced pressure, and the crude material was partitioned between methylene chloride and aqueous sodium hydrogen carbonate. The organic layer was dried (magnesium sulfate), filtered, evaporated and purified by chromatography on flash silica gel, eluting with 15% ethyl acetate/hexane to give 4-chloromethyl-thiazole-2-carboxylic acid ethyl ester (4.0 g, 37%) as an orange oil. 1HNMR (CDCl3): 6 7.64 (s, 1H), 4.78 (s, 2H), 4.51 (q, J=7.0 Hz, 2H), 1.46 (t, J=7.0 Hz, 3H). MS (APCI+): 206 (100).

The synthetic route of 16982-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
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Electric Literature of 758-96-3, 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 758-96-3 as follows.

General procedure: To a solution of 5-chloro-N-cyanothiophene-2-carboximidamide in CH3CN was added N,N-dimethylacetamide and POCl3. The mixture was stirred at 70 C overnight under N2. TLC showed starting material was consumed. The mixture was then poured into NaHCO3 (aq) carefully and the precipitate collected. The dried compound was taken to the next step without further purification.

According to the analysis of related databases, 758-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hagen, Timothy J.; Mo, Xuesheng; Burgin, Alex B.; Fox III, David; Zhang, Zheng; Gurney, Mark E.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 4031 – 4034;,
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Electric Literature of 122334-37-6, A common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, molecular formula is C9H10ClNO2, 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.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-4-(tert-butoxy)quinazoline (2.5 g, 8.89 mmol, 1.00 equiv) in tetrahydrofuran (100 mL). This was followed by the addition of n-BuLi (4.25 mL, 1.20 equiv) dropwise with stirring at -78 C. After 40 mins, to the mixture was added a solution of 4-chloro-N-methoxy-N-methylbenzamide (2.17 g, 10.87 mmol, 1.20 equiv) in tetrahydrofuran (20 mL). The resulting solution was stirred for another 30 min at 0 C. in a water/ice bath. The reaction was then quenched by the addition of water (10 mL), and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5), to yield of 4-(tert-butoxy)-6-[(4-chlorophenyl)carbonyl]quinazoline as a white solid.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Macielag, Mark Joseph; Zhang, Yue-Mei; DeCorte, Bart L.; Greco, Michael N.; (118 pag.)US2016/68512; (2016); A1;,
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Reference of 6973-09-7, 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. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, 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.

To a mixture of 5-amino-2-methylbenzenesulfonamide (20 gm) in ethanol (208 ml) and tetrahydrofuran (52 ml) was added 2,4-dichloropryrimidine (44 gm) and sodium bicarbonate (36 gm) at room temperature. The contents were heated to 70 to 75¡ã C. and maintained for 13 hours. The reaction mass was then cooled to 10¡ã C. and maintained for 2 hours. The reaction mass was filtered and the solvent was distilled off under vacuum at below 50 to 55¡ã C. to obtain a residual mass. To the residual mass was added ethyl acetate (100 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 15.5 gm of 5-(4-chloropyrimidin-2ylamino)-2-methylbenzenesulfonamide

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; HETERO RESEARCH FOUNDATION; Reddy, Bandi Parthasaradhi; Reddy, Kura Rathnakar; Reddy, Dasari Muralidhara; Rao, Thungathurthy Srinivasa; Krishna, Bandi Vamsi; US2013/245262; (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. 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., name: 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Intermediate 1 Preparation of 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoic acid To a solution of 2-chlorobenzoic acid (930.0 gm,5.96 mol) in cone, sulphuric acid (5580 ml), 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (930.0 gm ,6.0 mol) was added at 20 C and the reaction mixture was stirred for 15.0 h at 25-30 C. After the completion of the reaction, the reaction was slowly quenched with cold water (37.0 lit) at 10-15 C. The precipitated product was filtered and dried. The obtained product was purified using mixture of toluene and methylethylketone (7:1 x 4 times) to obtain 580.0 gm of the tittle compound having chemical purity of 98.0%, determined by HPLC.

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 50667-69-1.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; MUTHUKAMAN, Nagarajan; GHARAT, Laxmikant Atmaram; KADAM, Suresh Mahadev; GAVHANE, Sachin; KHANDAGALE, Sandeep Bandu; NIRGUDE, Sunil Pandurang; (59 pag.)WO2016/199104; (2016); 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. 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, A new synthetic method of this compound is introduced below., name: 4-Amino-2-fluoro-N-methylbenzamide

The mixture of 4-amino-2-fluoro-Nmethylbenzamide(22) (1.68 g, 10 mmol) [35], H2SO4 (0.68 mL) andwater (13 mL) was gently heated until all the components werecompletely dissolved. The mixture was cooled to 0e5 understirring, then the solution of NaNO2 (0.7 g,10 mmol) inwater (2 mL)was added dropwise. The resulting mixture was stirred at 0e5for 0.5 h and then slowly poured into the solution of KI (5 g) in coldwater (20 mL). The solutionwas then heated up to 80 and stirredfor 0.5 h. After cooling it was treated with 30 mL of chloroform andfiltered. The organic layer was washed with 5% Na2SO3 solution,dried over Na2SO4 and rotovapped. Column chromatography onsilica gel (hexane/EtOAc 6:1) afforded 2.33 g (83%) of 2-fluoro-4-iodo-N-methylbenzamide (37). MS (ESI) [MH] 280. 1H NMR(400 MHz, DMSO-d6) d 8.25 (m, 1H), 7.73 (d, J 10.0 Hz, 1H), 7.65 (d,J 7.8 Hz, 1H), 7.37 (t, J 7.8 Hz, 1H), 2.75 (d, J 4.4 Hz, 3H). Thesolution of compound 37 (9 g, 32 mmol) in DMF (25 mL) was addedto the ice cooled suspension of NaH (1.48 g, 36.8 mmol, 60% in oil,washed with hexane) in DMF (50 mL). The resulting mixture wasvigorously stirred for 0.5 h in an ice bath, then SEM-chloride (6.46 g,39 mmol) was added and the mixture was continuously stirredovernight at the ambient temperature. After the reaction wascompleted, the mixture was poured into water (400 mL) and theobtained product was extracted with benzene (2 200 mL),washed with water, dried over Na2SO4 and then filtered through3 cm layer of silica gel washing with 5:1 hexane/EtOAc. The solventwas evaporated in vacuo providing 11 g (84%) of 2-fluoro-4-iodo-Nmethyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide (40). MS(ESI) [MH] 520. 1H NMR (400 MHz, CDCl3) d 7.58 (m,1H), 7.52 (m,1H), 7.12 (m, 1H), 5.01 (s, 0.8H), 4.58 (s, 1.2H), 3.63 (t, J 8.2 Hz,0.8H), 3.31 (t, J 8.2 Hz, 1.2H), 3.14 (s, 1.8H), 2.92 (d, J 0.8 Hz,1.2H), 0.99 (t, J 8.2 Hz, 0.8H), 0.82 (t, J 8.2 Hz, 1.2H), 0.04 (s,3.6), 0.01 (s, 5.4). The mixture of 6.69 g (51 mmol) of aminoacid(R)-36a or 9.55 g of (R)-36b, 17.4 g (42.5 mmol) of 40, 1.62 g(8.5 mmol) of CuI, 23.5 g (0.17 mol) of K2CO3, 36mL of water,145mLof DMF and 3e5 drops of Et3N was stirred for 10 min, then 6.56 g (46.8 mmol) of 2-acetylcyclohexanone was added and stirringcontinued at 100 for 24 h. After cooling the mixture was rotovapped,the residue was treated with 200mL of water and acidifiedwith hydrochloric acid to 2e3 (~30 mL). Then 200 mL of etherwas added, the mixture was stirred for 0.5 h and the formed precipitatewas filtered off, washed with 50 mL of ether and dried invacuo to give 10.7 g (65%) of (R)-3-(3-fluoro-4-{methyl[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)-tetrahydrofuran-3-carboxylic acid ((R)-41) (55% from ester (R)-36b). MS (ESI)[MH] 413. 1H NMR (400 MHz, DMSO-d6) d 12.97 (brs, 1H), 7.07(m, 2H), 6.31 (brs, 1H), 6.17 (brs, 1H), 4.85 (brs, 0.67H), 4.60 (brs,1.33H), 4.10 (brs, 1H), 3.87 (brs, 3H), 3.51 (brs, 0.67H), 3.24 (brs,1.33H), 2.93 (s, 2H), 2.86 (brs, 1H), 2.56 (brs, 1H), 2.16 (brs, 1H), 0.89(brs, 0.67H), 0.73 (brs, 1.33H), 0.03 (m, 9H). The mixture of 10.7 g(26 mmol) of (R)-41 and 8.9 g (39 mmol) of 4-isothiocyanato-2-(trifluoromethyl)benzonitrile (42) [34] in pyridine (100 mL) wasstirred at 80 for 48 h. The residue formed after cooling androtovapping was then treated with ethyl acetate and filteredthrough 2 cm layer of silica gel. The solvent was removed underreduced pressure and the desired product was crystallized fromethanol to obtain 4.85 g (30%) of 4-{(R)-3-[4-cyano-3-(trifluoromethyl)phenyl]-4-oxo-2-thioxo-7-oxa-1,3-diazaspiro[4.4]non-1-yl}-2-fluoro-N-methyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide ((R)-43). MS (ESI) [MH] 623. 1H NMR (400 MHz,CDCl3) d 8.01 (d, J 8.0 Hz, 1), 7.98 (s, 1), 7.85 (d, J 8.0 Hz, 1),7.57 (m, 1), 7.28 (m, 1), 7.21 (m, 1), 5.06 (s, 0.8), 4.63 (s, 1.2),4.41 (d, J 10.4 Hz, 1), 4.16 (d, J 10.4 Hz, 1), 3.97 (q, J 7.6 Hz,1), 3.78 (m, 1), 3.66 (t, J 8.2 Hz, 0.8), 3.66 (t, J 8.2 Hz, 1.2),3.20 (s, 1.8), 2.99 (s, 0.8), 2.72 (m, 1), 2.47 (m, 1), 1.01 (t,J 8.2 Hz, 0.8), 0.83 (t, J 8.2 Hz, 1.2), 0.06 (s, 3.6), 0.01 (s,5.4). TFA (15 mL) was added to the solution of compound (R)-43(4.8 g, 7.7 mmol) in DCM (30 mL), then the resulting mixture wasstirred for 3 h. The solvent was removed under reduced pressureand the formed residue was subjected to column chromatographyon silica gel (CHCl3/MeOH 60:1) to give 2.96 g (78%) of desiredproduct (R)-6.

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:
Article; Ivachtchenko, Alexandre V.; Ivanenkov, Yan A.; Mitkin, Oleg D.; Vorobiev, Anton A.; Kuznetsova, Irina V.; Shevkun, Natalia A.; Koryakova, Angela G.; Karapetian, Ruben N.; Trifelenkov, Andrey S.; Kravchenko, Dmitry V.; Veselov, Mark S.; Chufarova, Nina V.; European Journal of Medicinal Chemistry; vol. 99; (2015); p. 51 – 66;,
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