Amides-buliding-blocks

Synthetic Route of 14062-80-7,Some common heterocyclic compound, 14062-80-7, name is 4-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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.

N’-cyanobenzimidamide (16.8 g, 115 mmol),Compound A-2 (21 g, 115 mmol) andPhosphorus oxychloride (12 mL, 128 mmol) was added to a solution ofAnd the mixture was added to 500 mL of acetonitrile, followed by stirring and refluxing for 1 hour. After cooling to room temperature, the resulting solid was filtered, washed with water and ethanol, and dried to give Compound A (27.6 g, yield 80%).

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-N,N-dimethylbenzamide, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Kang Min-yeong; Park Tae-yun; Cho Seong-mi; Moon Jeong-uk; Jeong Min-u; Lee Jeong-ha; Chae Mi-yeong; (30 pag.)KR2019/9211; (2019); A;,
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Application of 21440-97-1, The chemical industry reduces the impact on the environment during synthesis 21440-97-1, name is 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, I believe this compound will play a more active role in future production and life.

With a thermometer,Add 40g compound 17, to the 1L three-neck bottle of the condenser28.7 g carbazole, 32.3 g K2CO3, 0.62 g 1,10-Phenanthroline,Then 450 ml of DMF was added.Replace the air in the reaction system with nitrogen,Add 0.45 g of CuBr under nitrogen protection.Heat to 120 C for 10 h,After the TLC was monitored, the starting material was completely reacted and the stirring was stopped and lowered to room temperature.The reaction system is added to 3 volumes of water,The product was precipitated by stirring and filtered.The filter cake was completely dissolved in 500 ml of dichloromethane (DCM) and washed 3 times with water.150ml each time. The organic phase is dried and concentrated.The crude product was passed through a silica gel column to give compound 18 as a white solid, 43.1 g, yield 80.6%.

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, 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Yan; Yang Dandan; Gao Renxiao; (34 pag.)CN108912138; (2018); A;,
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Related Products of 14437-03-7, A common heterocyclic compound, 14437-03-7, name is Methyl tosylcarbamate, molecular formula is C9H11NO4S, 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: The 4-substituted methyl (phenylsulfonyl)carbamate was dissolved in the chosen alcohol (2 mL) in a microwave vial, which was closed using an aluminum open-top seal with PTFE-faced septum. The reaction mixture was heated under microwave irradiation at 100-120 oC for 20-60 min. The crude reaction mixture was concentrated under reduced pressure and the residue was purified using silica gel column chromatography to yield the desired (aryl)carbamate.

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; Isaksson, Rebecka; Kumpi?a, Ilze; Larhed, Mats; Wannberg, Johan; Tetrahedron Letters; vol. 57; 13; (2016); p. 1476 – 1478;,
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Reference of 83922-54-7, A common heterocyclic compound, 83922-54-7, name is 4-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, 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 the compound prepared in Reference Example 2 (100 mg) in dimethyl formamide (3 mL) was added acetic acid (16 muL) (or triethylamine (40 muL)). To the reaction mixture was added N-(4-formylphenyl)methanesulfonamide (56 mg) and sodium triacetoxyborohydride (82 mg). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, the obtained residue was purified by column chromatography on silica gel (ethyl acetate : methanol = 20 : 1-10 : 1) and 4N hydrogen chloride / ethyl acetate solution was added thereto. The reaction mixture was concentrated to give the compound of the present invention (72 mg) having the following physical data. TLC: Rf 0.67 (dichloromethane:methanol=5:1); NMR(CD3OD): delta 7.53, 7.34, 4.32, 4.15, 3.99, 3.74, 3.54-3.42, 3.33-3.16, 3.01, 2.49-2.24, 2.14- 1.91, 1.80-1.60, 1.40-1.15, 1.00-0.87.

The synthetic route of 83922-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1541574; (2005); A1;,
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Electric Literature of 2360-20-5, A common heterocyclic compound, 2360-20-5, name is 3,4-Diaminobenzenesulfonamide, molecular formula is C6H9N3O2S, 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 91 2-[4-(3-Chloro-4-fluoro-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-sulfonic Acid Amide. This compound was prepared according to the methods described in Example 22 and Scheme 3, substituting 4-(3-chloro-4-fluoro-phenylsulfanyl)-benzaldehyde for 4-(4-fluoro-phenoxy)-benzaldehyde, and 3,4-diamino-benzenesulfonamide for 3,4-diaminobenzamide. HPLC: Rt=8.57. MS (ESI+): mass calculated for C19H13ClFN3O2S2, 433.01; m/z found, 434.0 [M+H]+, 436.0 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.23 (d, J=1.6, 1H), 8.05 (d, J=8.7, 2H), 7.96-7.94 (dd, J=8.6, 1.6, 1H), 7.81 (d, J=8.5, 1H), 7.67-7.65 (dd, J=6.9, 2.3, 1H), 7.52-7.46 (m, 1H), 7.45 (d, J=8.7, 2H), 7.35 (t, J=8.8, 1H).

The synthetic route of 2360-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arienti, Kristen L.; Axe, Frank U.; Breitenbucher, J. Guy; Huang, Liming; Lee, Alice; McClure, Kelly J.; US2003/176438; (2003); A1;,
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Application of 112101-81-2, A common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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 4:Preparation of By-Product (5-((R)-2-{Bis-[2-(2-ethoxy phenoxy)ethyI]amino}-propyl)-2-methoxy benzene sulfonamide)This example demonstrates how by-product 5-((R)-2-{Bis-[2-(2-ethoxyphenoxy) ethyl]amino}-propyl)-2-methoxybenzenesulfonamide is prepared by reacting the (R)- enantiomer of reactant-V according to prior processes. A round-bottomed flask is charged with 4.0 g (16.37 mmol) of (R)-reactant-V, 3.47 g (32.74 mmol) OfNa2CO4, 8.01 g (32.65 mmol) of the bromide form of reactant-VI, and 24 mL of N,N-dimethylformamide. Notably, alkyl phosphite solvent was not used in this example. The mixture is heated up to 80 C, and is stirred overnight at 80 C, and then the mixture is cooled down to about 20-25 C. EPO At this point, 40 mL of water and 40 mL of AcOEt are charged into the flask and the resulting mixture is then stirred for 30 minutes and left to decant. The organic phase is separated and then charged again into the flask, is reintroduced in the flask and washed with slightly acidic water (pH 5). The mixture is let to decant and the organic phase is dried with Na2SO4 and the solvent evaporated to obtain 8.96 g of crude 5-((R)-2-{Bis-[2-(2- ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzene sulfonamide. The crude product was purified by silica gel column chromatography (AcOEt as eluent) to obtain 6.29 g of 5- ((R)-2- {Bis-2-(2-ethoxyphenoxy)ethyl]amino } -propyl)-2-methoxybenzenesulfonamide, which still was unpurified and contained unused reactant-VI. A second silica gel column chromatography (CHCI3 as eluent) was performed to obtain 6.00 g of purified 5-((R)-2-{Bis- [2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide (yield 64%).Prior to purification by gel column chromotography, the crude product has approximately 9% (area) tamsulosin free base and approximately 73.3% (area) of the byproduct. Following purification by gel column chromotography, tamsulosin free base is not detected according to HPLC method 1 analysis.The 1H-NMR pMSO-d6, 300 MHz), delta (ppm) of the byproduct is characterized as follows: 0.94 (d, 3H, NCHCH3); 1.24 (t, 6H, OCH2CH3); 2.49 (m (overlapped with DMSO-d5), IH, Ar- CHA); 2.84 (dd, IH, Ar-CHB); 2.89-3.05 (complex signal , 5H, N(CH2-)2 and NH-CHCH3); 3.83 (s, 3H, OCH3); 3.78-4.01 (complex signal, 8H52 OCH2CH3 and 2 NHCH2CH2O); 6.79-6.94 (complex signal, 8H, Ar-H of Ar-OEt); 6.97 (broad s, 2H SO2NH2); 7.00, (d, IH, 3-H (Ar- SO2NH2)); 7.41 (dd, IH, 4-H (Ar-SO2NH2); 7.57 (d, IH, 6-H (Ar-SO2NH2));The 13C NMR (DMSO-d6, 300 MHz), delta (ppm) of the byproduct is characterized as follows: 14.9 (2CH3, 2 OCH2CH3); 15.3 (CH3, CHCH3); 38.3 (CH2 , ArCH2); 50.1 (2 CH2, 2 OCH2CH2N); 56.1 (CH3, OCH3); 59.2 (CH, CHCH3); 63.9 (2 CH2, 2OCH2CH3); 68.6 (2 CH2, 2 OCH2CH2N); 112.4 (CH, C3 (Ar-SO2NH2)); 113.6 , 113.7 and 120.9 (2 x 4CH (Ar-OEt)); 128.1 (CH, C6 (Ar-SO2NH2); 130.9 and 132.3 (2 x C, Ci and C5 (Ar-SO2NH2)); 134.3 (CH, C4 (Ar-SO2NH2); 148.4 and 148.5 2 X 2C (Ar-OEt); 154.2 (C, C2 (Ar-SO2NH2).

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; MEDICHEM, S.A.; WO2007/4077; (2007); A2;,
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Related Products of 885-70-1, 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. 885-70-1, name is 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 20 L-5,11-Dihydro-11-[[6-methyl-2,6-diazabicyclo[3.3.0]oct-2-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one 2.6 g (0.021 mole) of L-2-methyl-2,6-diazabicyclo [3.3.0]octane were added dropwise to a mixture consisting of 11.2 ml of a 20% strength solution of phosgene in toluene, 50 ml of acetonitrile and 2.4 g (0.023 mole) of anhydrous sodium carbonate while externally cooling with ice. After 60 minutes, 4.5 g (0.021 mole) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were added and the mixture was heated under reflux for 4 hours. The hot mixture was filtered, the precipitate was washed three times using 10 ml of hot acetonitrile each time and the combined filtrates were concentrated in vacuo to a total volume of 15 ml. The solution was cooled in an ice bath and the resulting crystal paste was filtered under suction. Recrystallisation from acetonitrile produced 2.1 g (27% of theory) of colourless crystals of m.p. 220-222 C., identical to the preparation made as in Example 6c according to mixed melting point and spectroscopic data. 5,11-Dihydro-11-[[7-methyl-3,7-diazabicyclo[3.3.0]oct-3-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one of m.p. 157-159 C. (acetonitrile) 5,11-dihydro-11-[[10-methyl-4,10-diazatricyclo[5.2.1.02,6 ]dec-4- yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one of m.p. 218-220 C. (ethyl acetate) were obtained in corresponding manner.

The chemical industry reduces the impact on the environment during synthesis 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Rudolf; Klaus; Engel; Wolfhard; Eberlein; Wolfgang; Trummlitz; Gunter; Mihm; Gerhard; Doods; Henri; Mayer; Norbert; US5179090; (1993); A;,
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177210-33-2, name is 5-Hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one, 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 C8H7NO3

[00327] A solution of 5-hydroxy-2H-benzo[b][l,4]oxazin-3(4H)-one (100 mg, 0.604 mmol) and K2C03 (167 mg, 1.21 mmol) in anhydrous DMF (5 mL) was stirred at 27 C for 5 minutes, then ethyl 2-bromoacetate (121 mg, 0.727 mmol) was added. The reaction mixture was stirred at 27 C for 16 h and concentrated. MS (ESf ) e/z: 238.0 [M+l]+.

The synthetic route of 177210-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; WO2014/100734; (2014); A1;,
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Application of 621-38-5, A common heterocyclic compound, 621-38-5, name is 3-Bromoacetanilide, molecular formula is C8H8BrNO, 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: A dry argon-flushed Schlenk flask, equipped with a magnetic stirrer and a septum was charged with asolution of 1-iodo-1-(3′,4′,5′-trimethoxyphenyl)ethylene (48 mg, 0.15 mmol) in 1.5 mL of dry THF.The solution of i-PrMgCl¡¤LiCl (0.17 ml of 0.97 M solution in THF, 0.165 mmol) was added slowly at -20 C, and the reaction mixture was stirred at this temperature for 20 min to complete I/Mg exchange. 1 M solution of ZnCl2 (0.15 ml of 1 M solution in THF, 0.15 mmol) was added dropwise for 1 min at -20 C and the reaction mixture was warmed to room temperature. 3-(Methoxymethoxy)-4-methoxyphenyl iodide (44 mg, 0.15 mmol) was placed in a round bottom flask under argon. Solution of Pd(OAc)2 (1.35 mg, 0.006 mmol) and S-Phos (3.7 mg, 0.009 mmol) in 1 mlof THF was added, followed by dropwise addition of prepared solution of organo zinc reagent (0.15mmol) over a period of 1 min at room temperature. The reaction mixture was stirred at room temperature for 5 h, poured into saturated aq. NH4Cl solution and extracted with EtOAc. The organiclayer was washed with brine, dried over Na2SO4 and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc, 5:1) to give 5a-OMOM (44mg, 0.122 mmol, 81%) as brown oil.

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; Malysheva, Yulia B.; Buchvalova, Svetlana Y.; Svirshchevskaya, Elena V.; Fokin, Valery V.; Fedorov, Alexey Y.; Synlett; vol. 24; 14; (2013); p. 1772 – 1776;,
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Reference of 177210-33-2, These common heterocyclic compound, 177210-33-2, name is 5-Hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one, 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.

A suspension of 11 (2.00 g, 12.1 mmol), benzyl bromide (1.6 mL,13.3 mmol) and K2CO3 (2.35 g, 17.0 mmol) in acetone (60 mL) wasstirred at reflux for3 h.Themixturewascooled toroomtemperature,filteredand the solventwasevaporated.The residuewasdissolved in THF/glacial acetic acid 9:1 (70 mL) and bromine (680 lL, 13.3 mmol)was added dropwise. The reaction was stirred at room temperaturefor 2 h. Then, 1% Na2S2O3 solution (200 mL) was added and the mixturewas kept at 0 C for 18 h. The suspension was filtered and thesolid was dissolved in EtOAc. After the solvent was evaporated, theresidue was purified by flash chromatography (cyclohexane/EtOAc4:1) to give 12 as yellowish solid (2.8 g, 70% yield). IR: 3316, 3132,3079, 2955, 2842, 1660, 1610, 1565, 1485, 1455, 1377, 1266, 1169,835 cm1. 1H NMR (360 MHz, CDCl3) d (ppm) 4.69 (s, 2H), 5.08 (s,2H), 6.55 (d, J = 8.9 Hz, 1H), 7.11 (d, J = 8.9 Hz, 1H), 7.36-7.42 (m,5H), 7.86 (s, 1H). 13C NMR (90 MHz, CDCl3) d (ppm) 67.42, 71.30,102.09, 107.07, 116.86, 126.26, 127.81, 128.27, 128.85, 135.42,140.91, 144.96, 163.48. HR-EIMS calcd. 333.0001; found: 333.001.HPLC: System1: tR = 20.9 min, purity: 96.4%

Statistics shows that 5-Hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one is playing an increasingly important role. we look forward to future research findings about 177210-33-2.

Reference:
Article; Weichert, Dietmar; Stanek, Markus; Huebner, Harald; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2641 – 2653;,
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