Tag: M.W=200-300

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. 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate

To the solution of 4,6-dichloro-5-iodopyrimidine (5.50 g, 20.00 mmol) (prepared according to the ref of Organic Letters; English; 11; 8; 2009; 1837 – 1840; ) in dioxane (100 mL) was slowly added the solution of tert-butyl l-(4-aminophenyl)cyclobutylcarbamate (5.2 g, 20.00 mmol) in dioxane (20 mL) and Et3N(5 ml). The reaction mixture was stirred at 80C for overnight, lc-ms indicated 4,6-dichloro-5-iodopyrimidine was completed consumed. After removed the excess solvents under the reduced pressure to get a residue, which was dissolved in Ethyl acetate (250 mL) and washed water and brine. The combined organic layer was dried over Na2S04 and then filtered, the filtrate was concentrated to give the crude product, which was further purified by flash chromatography to afford tert-butyl l-(4-(6-chloro-5-iodopyrimidin-4- ylamino)phenyl)cyclobutylcarbamate. (5.00 g 50% yield).LC/MS: (ESI+): 501 [M+l], 523 [M+Na].

The synthetic route of 1259224-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
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Synthetic Route of 67341-01-9, 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. 67341-01-9, name is tert-Butyl (2-hydroxy-1-phenylethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-(2,6-difluoro-benzyl)-5-nitro-1H-pyrimidine-2,4-dione (82 mg, 0.29 mmol), ((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (69 mg, 0.29 mmol), and triphenylphosphine (114 mg, 0.44 mmol) were dissolved in anhydrous tetrahydrofuran (2 mL). To this solution was added diethyl azodicarboxylate (200mu?, 0.44 mmol), followed by stirring at room temperature for 4 hrs. The solution was concentrated, after which the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 3/1/1) and dried in a vacuum to afford 67 mg of the compound as a colorless oil (yield 67%). 1H NMR (300MHz, CDCl3) delta 1.30(9H, s), 3.40(1H, d), 4.50(1H, m), 5.08-5.27(4H, m), 7.02(2H, t), 7.26-7.47(6H, m), 8.78 (1H, s)

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, tert-Butyl (2-hydroxy-1-phenylethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sk Chemicals Co., Ltd.; EP2390250; (2011); A2;,
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Application of 25625-57-4,Some common heterocyclic compound, 25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, molecular formula is C9H7BrF3NO, 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 10a Chiral isomer 12-{3-[4-(4-methyl-1 H-imidazol-1 -yl)phenyl]-2-oxo-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-1 -yl}-N-[3-(trifluoromethyl)phenyl]acetamide hydrochloride 3-[4-(4-Methyl-1 H-imidazol-1 -yl)phenyl]-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D31 a), isomer 1 (94mg) in DMF (6ml) was cooled to ice bath temp and treated with sodium hydride 60% in oil (13mg) under an atmosphere of argon. The mixture was stirred for 20 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (85mg) in DMF (2.5ml) was added over 1.5 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The solvent was partially removed and the residue was purified by low pH MDAP. The fractions were loaded onto SCX and the free base was eluted with 2M methanolic ammonia. The solvent was removed and the residue was dissolved in DCM, treated with HCI-Et2O, solvent removed and a white solid was obtained from ether (78mg).1H NMR (DMSO) delta: 1.75 (2H, m), 2.05-2.35 (obs, m), 2.45 (3H, s), 3.4-3.6 (obs, m), 3.9 (2H, m), 4.98 (2H, m), 7.45 (1 H, m), 7.58 (1 H, m), 7.75 (1 H, m), 7.98 (2H, m), 8.12 (2H, m), 8.58 (2H, m), 9.63 (1 H, s), 10.74 (1 H, s). 19F NMR (DMSO) delta: 61.4 Mass Spectrum (LC/MS): Found 512 (MH+). Ret. time 1.63 min.Example 10b Chiral isomer 2 2-{3-[4-(4-methyl-1 H-imidazol-1 -yl)phenyl]-2-oxo-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en- 1-yl}-N-[3-(trifluoromethyl)phenyl]acetamide-‘J 3-[4-(4-Methyl-1 H-imidazol-1 -yl)phenyl]-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D31 b), isomer 2 (94mg) in DMF (6ml) was cooled to ice bath temp and treated with sodium hydride 60% in oil (12mg) under an atmosphere of argon. The mixture was stirred for 20 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (85mg) in DMF (2.5ml) was added over 1.5 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine and then dried with hydromatrix and the solvent was removed to give the title compound (104mg). 1H NMR (CDCI3) delta: 1.7 (obs, m), 2.0 (2H, m), 2.15-2.4 (2H, m), 3.31 (3H, m), 3.71 (1 H, m), 3.85 (2H, m), 4.05 (1 H, m), 4.45 (2H, m), 7.10 (1 H, s), 7.3-7.5 (4H, m), 7.68 (1 H, m), 7.84 (1 H, m), 7.94 (1 H, m), 8.60 (2H, m), 9.09 (1 H, s). 19F NMR (DMSO) delta: 62.7 Mass Spectrum (LC/MS): Found 512 (MH+). Ret. time 1.62 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Amide – Wikipedia,
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Electric Literature of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl-N-(tert-butoxycarbonyloxy) carbamate (224 mg, 0.96 mmol) in DMF (2 [MNo.) ] was reacted with sodium hydride (38 mg, 0.96 mmol) at [0 C] and stirred for 20 mins at room temperature. The reaction mixture was treated by dropwise addition of benzyl [N- [4- (BROMOMETHYL)-2-FLUOROPHENYL]] carbamate compound 52 (250 mg, 0.74 mmol) and stirred for 1 hour. After concentrating, residual mixture was purified by column chromatography on Silica gel with EtOAc/hexanes (1: 5) solvent mixture as an eluant to give 355 mg of yellow oil of tert-butyl [N-[(TERT-BUTOXYVARBONYL) OXY]-N-{4-] [[(BENZYLOXY) CARBONYLAMINO]-3-FLUOROBENZYL} CARBAMATE] compound 53 (yield: [98%).] 1H-NMR [(CDC13)] 8 : 8.06 (bt, 1 H), 7.35-7. 45 (m, 5 H, Ph), 7.05-7. 12 (m, 2 H), 6.89 (bs, 1 H, NH), 5.22 (s, 2 H, [OCH2PH),] 4.68 (s, 2 H, CH2NO), 1.48 (s, 9 H, C [(CH3)] 3), 1.47 (s, 9 H, [ C (CH3) 3)]

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Digital Biotech Co., Ltd.; WO2004/35533; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53844-02-3,Some common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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.

Treat a -78 C solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, drop-wise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to -30 C for 0.5 h, re-cool to -78C and treat drop-wise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at -78C for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at – 78C for 1 h, then warm to RT and stir overnight. Treat the mixture with H20, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2S04, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21 % yield). MS (m/z): 247.2 (M+l).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; ELI LILLY AND COMPANY; FLYNN, Daniel L.; KAUFMAN, Michael D.; VOGETI, Lakshminarayana; WISE, Scott C.; LU, Wei-Ping; SMITH, Bryan D.; CALDWELL, Timothy M.; PATT, William C.; HENRY, James Robert; HIPSKIND, Philip Arthur; PENG, Sheng-Bin; WO2013/134298; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27466-83-7, name is 4-Bromo-N-methylbenzamide, 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 27466-83-7, Computed Properties of C8H8BrNO

General procedure: To a dried screw-capped vial were added benzamide 2 (0.10mmol), ethyl acrylate 3 (0.15mmol), 1b (4.8mg, 0.01mmol), AgSbF6 (6.8mg, 0.02mmol), AgOAc (41.7mg, 0.25mmol), and 1,2-dichloroethane (1.0mL) under Ar atmosphere. The vial was capped and the mixture was heated at 60C for 13h with stirring. After the mixture was cooled to room temperature, saturated EDTA·2Na aqwas added following dilution with CH2Cl2. Organic layer was separated and aqueous layer was extracted with CH2Cl2 (×2). Combined organic layers were dried over Na2SO4. After filtration and evaporation, obtained crude mixture was purified by silica gel column chromatography (CH2Cl2/EtOAc) to give product3.4.1.1 _4.1.5 (E)-Ethyl 3-(5-bromo-2-(methylcarbamoyl)phenyl)acrylate (4e) A colorless solid; IR (KBr) nu 3079, 2975, 2935, 1719, 1642, 1561, 1316, 1190, 1032, 979, 862 cm-1; 1H NMR (CDCl3, 400 MHz) delta 1.32 (t, J=7.5 Hz, 3H), 3.00 (d, J=5.2 Hz, 3H), 4.23 (q, J=7.5 Hz, 2H), 5.88 (br s, 1H), 6.36 (d, J=16.0 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.49 (d, J=8.6 Hz, 1H), 7.74 (s, 1H), 7.90 (d, J=16.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 14.4, 27.1, 60.1, 122.1, 124.1, 124.7, 129.3, 130.1, 132.7, 134.9, 135.8, 140.5, 166.2, 168.5; HRMS (ESI): m/z calculated for [M+Na]+: 334.0049, found: 334.0050.

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:
Article; Suzuki, Yudai; Sun, Bo; Yoshino, Tatsuhiko; Kanai, Motomu; Matsunaga, Shigeki; Tetrahedron; vol. 71; 26-27; (2015); p. 4552 – 4556;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, 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. category: amides-buliding-blocks

The Schiff base HL1 was synthesized with a method differentfrom the one in the literature [24], by refluxing sulfacetamide(1 mmol, 0.214 g) and salicylaldehyde (1 mmol, 0.122 g) in about15 ml of methanol for 3 h at ca.70 C, in the presence of 4-5 dropsof conc. H2SO4. The solid product was collected through filtrationand finally air dried. Yield: 58%. M.P. = 215 C. Anal. Calcd. forC15H14N2O4S (%):C, 56.59; H, 4.43; N, 8.80. Found: C, 56.42; H,4.25; N, 8.75. FT-IR (KBr, cm1): mmax cm1 (KBr):1645 (s, CN),1715 (CO), 1575, 1616 (CCaromatic), 1093, 1157 (SO2) 3340(NAH). UV-vis: kmax (nm) (e, M1 cm1) (DMSO-d6): 350(40,000), 320 (41,000). 1H NMR (DMSO-d6, 400 MHz):6-8 (m, 8H), 9 (s, 1H), 10 (s, 1H), 3 (s, 3H), 11 (s, 1H).

The synthetic route of N-((4-Aminophenyl)sulfonyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salehi, Mehdi; Ghasemi, Fateme; Kubicki, Maciej; Asadi, Asadollah; Behzad, Mahdi; Ghasemi, Mohammad Hadi; Gholizadeh, Ahmad; Inorganica Chimica Acta; vol. 453; (2016); p. 238 – 246;,
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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. 2886-65-9, name is 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

EXAMPLE 3 Preparation of 10-chloro-11b-(2-fluorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6-(7H)-one SPC17 To 15 g. (51.9 mmole) of 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 150 ml. of dry benzene, 9 g. (67.7 mmole) of aluminum chloride was added and stirring was continued 15 minutes. The reaction mixture was cooled in an ice bath and 8.8 g. (0.2 mole) of ethylene oxide was added dropwise. After 18 hours of stirring at room temperature, the reaction mixture was heated to 40 for 1 hour and then cooled to room temperature and treated with 5 g. (37.6 mmole) of aluminum chloride, followed by 4.4 g. (0.1 mole) of ethylene oxide. The reaction mixture was heated 4 hours at 45-50 and then evaporated to dryness. ethylene chloride, ice and ammonium hydroxide were added and the solid removed by filtration. The filtrate was separated and the organic phase reduced to dryness in vacuo. The residue was dissolved in dilute hydrochloric acid and the pH of the solution adjusted to 5 with ammonium hydroxide. The acidic solution was washed with ether, made basic and extracted with methylene chloride. The organic phase was washed with brine, dried and evaporated to dryness. Recrystallization from methylene chloride-hexane gave the above-titled product as colorless rods, m.p. 183-184.

The synthetic route of 2886-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US3965151; (1976); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 4943-86-6, These common heterocyclic compound, 4943-86-6, name is 2-Amino-N-(4-chlorophenyl)benzamide, 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 solution of the substituted benzamide (1equiv) and ortho-bromobenzaldehyde(1.41 mmol, 1 equiv) in acetonitrile (5mL) was treated with cyanuric chloride(0.022 mmol, 10 mole %). The reaction mixture was stirred at room temperature for 5-10 min and formed precipitate was filtered and recrystallised with ethanol to obtain the compounds 1, 6a, 6b and 16.

Statistics shows that 2-Amino-N-(4-chlorophenyl)benzamide is playing an increasingly important role. we look forward to future research findings about 4943-86-6.

Reference:
Article; Sharma, Moni; Mahar, Rohit; Shukla, Sanjeev K.; Kant, Ruchir; Chauhan, Prem M.S.; Tetrahedron Letters; vol. 54; 46; (2013); p. 6171 – 6177;,
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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. 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11NO5S

(4) Add 245 g (1.0 mol) of methyl 2-methoxy-5-sulfamoylbenzoate prepared in step (3) and 2772 g of 5% sodium hydroxide solution by weight to the reactor, Stir the reaction for 20 h, and the reaction temperature does not exceed 40 . After the reaction, adjust the pH to 1 with 5% by weight of dilute hydrochloric acid and filter. The resulting filter cake is washed with water, dried, and recrystallized from methanol to produce 209.06 g of 2-methoxy-5-sulfamoylbenzoic acid, yield 90.5%.

According to the analysis of related databases, 33045-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suzhou Chenghe Pharmaceutical And Chemical Co., Ltd.; Chen Xiaoqiang; Fang Huan; (7 pag.)CN111100042; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics