Tag: M.W=100-200

Application of 402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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 13; 4-Fluoro-{N-4-[N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino]- benzoyl} benzenesulfonamide; A mixture of 4- [N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoic acid (50 mg, 0.14 mmol), 4-fluorobenzenesulfonamide (49 mg, 0. 28 mmol), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (54 mg, 0.28 mmol), and dimethylaminopyridine (35 mg, 0.28 mmol) was taken up in dichloromethane (1 mL) and stirred for 18h. The mixture was partitioned between EtOAc (50 mL) and 20% aqueous NH40Ac. The EtOAc was separated, washed with brine, dried (MgS04) and concentrated. The residue was purified by column chromatography (silica gel) eluting with 100% EtOAc to give 38 mg of 4-fluoro-f N 4- [N (3-fluoro-4- methoxyphenyl)-pyridin-3-ylmethylamino]-benzoyl} benzenesulfonamide as a white solid. IH NMR (300 MHz, CDC13) 6 8.5-8. 4 (m, 2H), 8. 11 (m, 2H), 7.7-7. 5 (m, 3H), 7.25 (m, 1H), 7.16 (m, 2H), 7.0-6. 8 (m, 3H), 6.63 (d, J=9.0, 2H), 4.92 (s, 2H), 3.89 (s, 3H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/61458; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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. Safety of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 C) and stirred for 30 min. The reaction mixture was warmed to 0 C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74%) of compound 1. 1H-NMR (300MHz, CDC13): delta = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57561-39-4, its application will become more common. Reference:
Patent; SYNTARGA B.V.; BEUSKER, Patrick, Henry; COUMANS, Rudy, Gerardus, Elisabeth; ELGERSMA, Ronald, Christiaan; MENGE, Wiro, Michael, Petrus, Bernardus; JOOSTEN, Johannes, Albertus, Frederikus; SPIJKER, Henri, Johannes; DE GROOT, Franciscus, Marinus, Hendrikus; WO2011/133039; (2011); A2;,
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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. 70-55-3, name is 4-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methylbenzenesulfonamide

Example 3 p-Aminosulfonyl-benzoic Acid To the solution of 17.1 g (0.1 mol) of p-toluenesulfonamide prepared in Example 1, 20 g (0.5 mol) of sodium hydroxide in 300 ml of water was added in portions 20 g (0.13 mol) of potassium permanganate. The temperature raised to 70 C. spontaneously, keep the reaction mixture in 90 C. for 2 h. The mixture was then cooled and filtered, and the filtrate was acidified with HCl. The resulting precipitate was filtered, and washed with water, dried in vacuo to give the title compound (18.1 g) as white powder, yield 90%, m.p. 291-292 C.

The synthetic route of 70-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Zongru; Cheng, Guifang; Chu, Fengming; US2004/58977; (2004); A1;,
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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. 6873-44-5, name is 4-Chloro-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6873-44-5

EXAMPLE IV N-Methyl 4-Chlorobenzimidoyl Chloride N-Methyl 4-chlorobenzamide (42.6 g, 251 mmole) and thionyl chloride (153.3 g, 1.28 mole) were reacted as in Example I to yield 39.3 g (83.4%) of the title compound, b.p. 125 C. (15 mm Hg).

The synthetic route of 6873-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US4528382; (1985); A;,
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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. 156731-40-7, name is 1-(Boc-amino)-3-butene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(Boc-amino)-3-butene

Freshly distilled acrolein (2.5ml, 2.1g, 38mmol) and CSA (175mg, 0.752mmol) were added to an ice-cooled solution of N-Boc-butenylamine 25 (644mg, 3.76mmol) in CH2Cl2 (8ml). The resulting solution was stirred at 0C for 15min and at ambient temperature for 45min. The mixture was then washed with satd NaHCO3 solution (10ml) and the organic layer dried (MgSO4). After filtration, the solvent was removed and the residue purified by chromatography on SiO2 (hexane/MTBE 1:1, Rf=0.36) to yield title compound 26 (684mg, 3.01mmol, 80%) as a colorless oil. 1H NMR (500MHz, CDCl3): delta=1.40 (s, 9H), 2.18-2.27 (m, 2H), 2.62-2.70 (m, 2H), 3.17-3.26 (m, 2H), 3.42-3.51 (m, 2H), 4.95-5.06 (m, 2H), 5.66-5.78 (m, 1H), 9.75 (t, J=1.6Hz, 1H)ppm. 13C{1H} NMR (125MHz, CDCl3): delta=28.27 (3CH3), 32.68 (CH2), 33.28 (CH2), 41.24 (CH2), 43.27 (CH2), 43.68 (CH2), 47.02 (CH2), 47.52 (CH2), 79.68 (C), 116.68 (CH2), 135.18 (CH), 154.99 (C), 155.34 (C), 200.72 (CH), 201.03 (CH)ppm. IR (ATR): 3077 (w), 2976 (m), 2930 (w), 1688 (vs), 1478 (m), 1415 (s), 1366 (s), 1249 (m), 1167 (vs), 1064 (m), 913 (m), 773 (m)cm-1. HRMS (CI, isobutane): calcd 228.1600 (for C12H22NO3), found 228.1603 [M+H+]. C12H21NO3 227.30.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wuerdemann, Martina; Christoffers, Jens; Tetrahedron; vol. 70; 31; (2014); p. 4640 – 4644;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

78191-00-1, name is N-Methoxy-N-methylacetamide, 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. Application In Synthesis of N-Methoxy-N-methylacetamide

Toluene-4-sulfonic acid 6-bromo-pyridin-3-yl ester (XVI) (980 mg, 2.99 mmol) was dissolved in tetrahydrofuran (THF) (3 mL) and the resulting solution was cooled to -78 C. 2.0 M lithium diisopropylamide (LDA) (2.24 mL, 4.48 mmol) dissolved in tetrahydrofuran was slowly added dropwise to the solution and the solution was stirred at -78 C for 3 hrs. And then, N-methoxy-N-methyl acetamide (609.77 muL, 5.97 mmol) was slowly added dropwise to the solution and the solution was stirred for 2 hrs. Saturated sodium hydrogen carbonate (NaHCO3) solution was added dropwise to the solution and the solution was diluted with ethylacetate (EA). Then, the organic solvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated under reduced pressure to concentrate. The resulting residue was isolated and purified by silica gel column chromatography (n-Hex/EA = 4/1) to give the title compound (570 mg, 52 %). 1H NMR (400 MHz, CDCl3) delta 7.97 (s, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 8.0 Hz, 2H), 2.58 (s, 3H), 2.49 (s, 3H).

The synthetic route of 78191-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
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Electric Literature of 193751-54-1, 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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

6.63 g of mCPBA (70%) was added at 0C to a solution of 4.7 g of N-Boc-cyclopent-3-enyl amine in 80 mL of DCM. The solution obtained was stirred at rt for 1.5 h, charged with 20 mL of 20% sodium thiosulfate, stirred for 10 min, DCM was added, phases obtained were separated and the organic layer obtained was washed with saturated NaHC03 solution. The aqueous layer obtained was extracted twice with DCM, the combined organic layers obtained were dried over magnesium sulfate and solvent was evaporated. 5.2 g of the crude product was obtained which was recrystallized twice from heptane. 917 mg of syn epoxide was obtained in the form of white needles. The mother liquors obtained were subjected to chromatography (silica, toluene/EtOAc = 9: 1 – 7: 1). 3.51 g of anti epoxide in the form of a white amorphous solid was obtained.Syn epoxide: NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.36 (s, 9H), 6.79 (d, 1H, J=8Hz), 1.47 (dd, 1H, J=8Hz and 14Hz), 2.17 (dd, 1H, J=8Hz and 14Hz), 3.44 (s, 2H), 3.54 (m, 1H). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.4.Anti epoxide: 1H NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.35 (s, 9H), 1.78 (d, 2H, J=15Hz), 1.98 (dd, 1H, J=8Hz and 15Hz), 3.51 (s, 2H), 3.89 (q, 1H, J=8 and 16Hz), 5.70 (d, 1H, J=8Hz). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3: 1, Rf = 0.45.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl cyclopent-3-en-1-ylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NABRIVA THERAPEUTICS AG; RIEDL, Rosemarie; THIRRING, Klaus; HEILMAYER, Werner; WO2012/31307; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, name is 4-Fluorobenzenesulfonamide, 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. HPLC of Formula: C6H6FNO2S

To a solution of 4-fluorobenzenesulfonamide (1 .02 g, 5.71 mmol) in H20 (10 mL) was added piperazine (2.46 g, 28.55 mmol). The reaction mixture was stirred at 100 00 overnight. The mixture was cooled to room temperature and filtered. The filtration cake was washed with H20 (20 mL), toluene(30 mL) and ether (30 mL) to give 26.1 (401 mg, 29% yield). MS (ESI) m/z = 242.0 [M¡ÂH]. 1H NMR (400 M, DMSO-c), oe 7.60 (d, J = 8.8 Hz, 2H), 7.05 (m, 2H), 7.00 (d, J = 8.8 Hz, 2H), 3.17 (m, 4H), 2.80 (m, 4H), 2.33 (m, 1H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNITY BIOTECHNOLOGY, INC.; BACKES, Bradley; W. VON GELDERN, Thomas; CHEN, Bing; (121 pag.)WO2017/101851; (2017); A1;,
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Amide – an overview | ScienceDirect Topics

Reference of 21744-84-3, 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. 21744-84-3, name is 4-Methyl-2H-1,4-Benzoxazin-3-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (2-chloro-5-methoxy-phenyl)-acetic acid (1 g) in tetrahydrofuran (20 ml) were added N,N-dimethylformamide (2 drops) and oxalylchloride (1.03 g). The mixture was stirred overnight at room temperature. The solvent was evaporated; toluene was added and again evaporated. The residue was dried under high vacuum to give the crude acid chloride. To a cooled solution (ice bath) of 4-methyl-2H-1,4-benzoxazin-3(4H)-one (830 mg) in 1,2-dichloroethane (5 ml) was added AlCl3 (1.99 g). The mixture was stirred for 10 min and a solution of the acid chloride in 1,2-dichloroethane (5 ml) was added dropwise. The mixture was stirred at 0 C. for 4.5 h. The mixture was poured into ice water and hydrochloric acid and extracted with dichloromethane. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1_0=>0:1) to give the title compound (1.6 g) as an off-white solid. MS (m/e)=346.1 [M+H-].

The synthetic route of 4-Methyl-2H-1,4-Benzoxazin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one, belongs to amides-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 89976-75-0, Quality Control of 6-Amino-2H-1,4-benzoxazin-3(4H)-one

Ci 6-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]- 4H-benzo[l, 4] oxazin-3-one:To a solution of ter.pound.-butyl-dimethyl-((5)-l-oxiranylmethoxy)-silane (commercial; 10.0 g, 53 mmol) in MeCN (16O mL) was added LiClO4 (16.9 g, 159 mmol). 6-amino- 4H-benzo[l,4]oxazin-3-one (commercial; 8.72 g, 53.1 mmol) was added and the mixture was stirred at 500C for 6 h. The solvent was removed in vacuo and the residue was purified by CC (DCM/MeOeta/Neta4Oeta 1000:25:2 -> 1000: 100:2) to afford the title compound as a pale brown foam (10.24 g, 55percent yield). MS (ESI, m/z): 353.3 [M+H+].

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-Amino-2H-1,4-benzoxazin-3(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/104159; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics