Tag: M.W=300-400

Reference of 1195768-19-4, A common heterocyclic compound, 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, molecular formula is C14H10F3NO4S, 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.

Step B: N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6- difluorobenzenesulfonamide Methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (490 g, 1 equiv.), prepared generally in accordance with Step A, above, was dissolved in THF (2.45 L, 5 vols) and stirred and cooled to 0-3 C. 1M lithium bis(trimethylsilyl)amide in THF (5.25 L, 3.7 equiv.) solution was charged to the reaction mixture followed addition of 2- chloro-4-methylpyrimidine (238 g, 1.3 equiv.) in THF (2.45 L, 5 vols). The reaction was then stirred for 1 hr. The reaction was quenched with 4.5M HC1 (3.92 L, 8 vols). The aqueous layer (bootom layer) was removed and discarded. The organic layer was concentrated under reduced pressure to ~2L. IP AC (isopropyl acetate) (2.45L) was added to the reaction mixture which was then concentrated to ~2L. IP AC (0.5L) and MTBE (2.45 L) was added and stirred overnight under N2. The solids were filtered. The solids and mother filtrate added back together and stirred for several hours. The solids were filtered and washed with MTBE (~5 vol). The solids were placed in vacuum oven at 50 C overnight. The solids were dried in vacuum oven at 30 C over weekend to obtain N-{3- [(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (479 g, 72%).

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; GRESHOCK, Joel David; HOOS, Axel; WO2015/87279; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1195768-19-4,Some common heterocyclic compound, 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, molecular formula is C14H10F3NO4S, 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.

Step D: N-{3-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; In a 1000 mL flask was placed methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (9.64 g, 27.9 mmol) and THF (200 mL) was added. The flask was placed in an ice/water bath and LiHMDS (90 mL, 90 mmol) was added. 2-Chloro-4-methylpyrimidine (4.5 g, 35.0 mmol) in THF (60 mL) was added dropwise via addition funnel. After the addition was complete, the reaction was allowed to warm to 20 C. over 1 h. The THF volume was reduced to half under reduced pressure and then treated with 6 N HCl. EtOAc was added and the layers were separated. The aqueous layer was extracted twice with EtOAc and the combined organic layer was washed once with brine, dried over NaSO4, and concentrated. The residue was triturated with EtOAc/ether to afford 8.71 g (71%) of the title compound of Step D. MS (ESI): 442 [M+H]+.

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1280210-80-1, The chemical industry reduces the impact on the environment during synthesis 1280210-80-1, name is MK-3102 interMediate3, I believe this compound will play a more active role in future production and life.

Step A: tert-Butyl { (2R.3S,5R)-2-(2,5-difluorophenyl)-5- [2-(methylsulfonyl)-2,6- dihydropyrrolo [3 ,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl } carbamateA vessel was charged with N,N-dimethylacetamide (520.6 kg), 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate (intermediate 2, 30.0 kg, 86.8 mol), and tert-butyl [(2R,35)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3 -yl]carbamate (intermediate 1, 31.2 kg, 95.3 mol). After dissolving at room temperature, the solution was cooled to 0-10 C and sodium triacetoxyborohydride (24 kg, 113 mol) was added in four equalportions every 40 mm. The reaction was then allowed to warm to room temperature and stirred an additional 5h. The solution was then cooled to 5-15 C and water (672 kg) was added over 1- 2h. The resulting slurry was filtered and the cake washed sequentially with N,Ndimethylacetamide, twice with water, and then n-heptane. The solids were dried under vacuum at 40-60 C to give tert-butyl { (2R,3S,5R)-2-(2,5-difluorophenyl)-5 – [2-(methylsulfonyl)-2,6-dihydropyrrolo [3 ,4-cjpyrazol-5(41])-yljtetrahydro-2H-pyran-3-yl } carbamate.

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, MK-3102 interMediate3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARROYO, Itzia; KRUEGER, Davida; CHEN, Ping; MOMENT, Aaron; BIFTU, Tesfaye; SHEEN, Faye; ZHANG, Yanfeng; MERCK SHARPE & DOHME LTD.; WO2013/3249; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 340187-12-4, These common heterocyclic compound, 340187-12-4, name is (9H-Fluoren-9-yl)methyl (2-bromoethyl)carbamate, 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 mixture of Example 123 (21 mg, 0.05 mmol), (9H-fluoren-9-yl)methyl2- bromoethylcarbamate (36 mg, 0.1 mmol) and K2CO3 (20 mg, 0.15 mmol) in DMF (1 mL) was stirred stirred at rt overnight. Piperidine (0.5 mL) was added and the mixture was stirred for another hour. The reaction mixture was purified by etaPLC to afford the product as a white solid. 1H-NMR (400 MHz, CD3CN) delta = 7.97 (br s, 2H), 7.04 (d, J = 8.1 Hz, IH), 6.76 (dd, J = 2.8, 8.4 Hz, IH), 6.72 (d, J = 2.4 Hz, IH), 4.75 (t, J = 5.6 Hz, 2H), 4.31 (s, 2H), 4.02 (m, 2H), 3.95 (t, J = 6.4 Hz, 2H), 3.49 (t, J = 5.6 Hz, 2H), 3.45 (t, 7 = 6.0 Hz, 2H), 2.93-2.86 (m, 4H), 2.80 (s, 3H), 1.80-1.76 (m, 4H), 1.53 (m, IH), 1.43- 1.38 (m, 2H), 1.24 (ddd, J = 4.0, 12.4, 24.2 Hz, 2H); MS calcd. for [M+H]+ C2iH34N7O3S: 464.2; found: 464.2.

The synthetic route of 340187-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/97428; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 340187-12-4, These common heterocyclic compound, 340187-12-4, name is (9H-Fluoren-9-yl)methyl (2-bromoethyl)carbamate, 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 mixture of Example 123 (21 mg, 0.05 mmol), (9H-fluoren-9-yl)methyl2- bromoethylcarbamate (36 mg, 0.1 mmol) and K2CO3 (20 mg, 0.15 mmol) in DMF (1 mL) was stirred stirred at rt overnight. Piperidine (0.5 mL) was added and the mixture was stirred for another hour. The reaction mixture was purified by etaPLC to afford the product as a white solid. 1H-NMR (400 MHz, CD3CN) delta = 7.97 (br s, 2H), 7.04 (d, J = 8.1 Hz, IH), 6.76 (dd, J = 2.8, 8.4 Hz, IH), 6.72 (d, J = 2.4 Hz, IH), 4.75 (t, J = 5.6 Hz, 2H), 4.31 (s, 2H), 4.02 (m, 2H), 3.95 (t, J = 6.4 Hz, 2H), 3.49 (t, J = 5.6 Hz, 2H), 3.45 (t, 7 = 6.0 Hz, 2H), 2.93-2.86 (m, 4H), 2.80 (s, 3H), 1.80-1.76 (m, 4H), 1.53 (m, IH), 1.43- 1.38 (m, 2H), 1.24 (ddd, J = 4.0, 12.4, 24.2 Hz, 2H); MS calcd. for [M+H]+ C2iH34N7O3S: 464.2; found: 464.2.

The synthetic route of 340187-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/97428; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, 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. Application In Synthesis of N-(Benzyloxy)-2-nitrobenzenesulfonamide

To a solution of fe/ -butyl (3S,4aS,7aS)-6-allyl-3-hydroxy-7-oxooctahydro-1 H-pyrrolo[3,4- b]pyridine-1 -carboxylate (786.4 mg, 2.65 mmol), /V-(benzyloxy)-2-nitrobenzenesulfonamide (900 mg, 2.92 mmol) and triphenylphosphine (835 mg, 3.18 mmol) in THF (29 mL) at -17 C was added DIAD (0.640 mL, 3.18 mmol) as a soln in THF (4.1 mL) drop-wise at 6:30 pm. It was allowed to slowly warm to rt and stir for 22 h then concentrated in vacuo and purified directly via silica gel chromatography (EtOAc-heptane, 0-40%), affording the title compound (846 mg, 54%) as an off-white solid. LCMS: Rt = 0.95 min; m/z = 587.3 (M+1 ) Method 2m acidic.

The synthetic route of N-(Benzyloxy)-2-nitrobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CASAREZ, Anthony; FUREGATI, Markus; KOCH, Guido; LIN, Xiaodong; OSSOLA, Flavio; RECK, Folkert; SIMMONS, Robert Lowell; ZHU, Qingming; (113 pag.)WO2018/60926; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 120157-97-3, 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. 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of teit-butyl N-[2-(4-bromophenyl)ethyl]carbamate, Intermediate 29 (4.09 g,13.6 mmol), [4-cyanomethyl)phenyl]boronic acid (2.63 g, 16.4 mmol) and K2C03 (5.65 g,40.9 mmol) in 1,4-dioxane (105 ml) was degassed by bubbling a stream nitrogen throughthe mixture for 5 mm. Pd(dppf)C12.CH2CI2 (445 mg, 0.545 mmol) was added anddegassing was continued for a further 5 mm. The reaction mixture was heated at 80 Cfor 15 h then at 100 C for 7 h. The reaction was allowed to cool to RT then retreated with K2C03 (3.76 g, 27.2 mmol) and degassed for 5 mm. Pd(dppf)C12.CH2CI2 (445 mg, 0.545 mmol) was added then the mixture was degassed for a further 5 mm. The resultant mixture was heated at 100 C for 24 h then allowed to cool to RT. The reaction wasretreated with K2C03 (1.88 g, 13.6 mmol) and [4-cyanomethyl)phenyl]boronic acid (0.88 g, 5.5 mmol) then degassed for 10 mm. Pd(dppf)C12.CH2CI2 (445 mg, 0.545 mmol) was added then the mixture was degassed for a further 5 mm. The reaction was heated at 100 C for 18 h then allowed to cool to RT. The reaction mixture was filtered then the collected solids were washed with EtOAc (50 ml). The combined filtrate wasconcentrated in vacuo. The residue was re-dissolved in EtOAc:heptane (1:1) then filtered through a silica pad. The pad was rinsed with EtOAc:heptane (1:1, 200 ml). The filtrate was concentrated in vacuo to afford an off-white solid (3.94 g). The silica pad was rinsed through further with EtOAc (200 ml) to afford a brown solid (1.68 g). The brown solid from the EtOAc filtrate was pre-adsorbed onto silica, then purified by flash columnchromatography on a silica column (50 g). The column was eluted with EtOAc:heptane, using the following gradient (%EtOAc, column volumes): 0%, 1 CV; 0-30%, 11 CV; 30%, 20 CV; 30-45%, 4.5 CV; 45%, 7.5 CV; 45-50%, 1 CV; 50%, 15 CV. The desired fractionswere combined and concentrated in vacuo to afford an off-white solid (1.00 g, 21%).1H NMR (500 MHz, DMSO-d6) O 7.67 (d, J= 8.2 Hz, 2H), 7.59 (d, J= 8.2 Hz, 2H), 7.42(d, J= 8.2 Hz, 2H), 7.28 (d, J= 8.1 Hz, 2H), 6.90 (t, J= 5.5 Hz, 1H), 4.07 (5, 2H), 3.17(q, J = 6.5 Hz, 2H), 2.73 (t, J = 7.4 Hz, 2H), 1.44 – 1.29 (m, 9H).LC/MS (System A): R = 1.27 mi UV purity = 97%.

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, N-Boc-2-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; MCCARTHY, Clive; (108 pag.)WO2019/77340; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 811442-84-9, name is tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

General Procedure XX. PEG Monomethacrylates. Preparation of Compound 43-1 To a solution of mono-Boc-protected PEG4 diamine (1.0 g, 2.97 mmol) in chloroform (30 mL), methacrylic anhydride (0.55 mL, 3.46 mmol) and triethylamine (0.55 mL, 3.95 mmol) were successively added, and the reaction mixture was stirred at room temperature overnight. Then the reaction mixture was concentrated under reduced pressure and the residue was taken up into EtOAc (40 mL). The solution was washed with 1 N HCl (2*40 mL), saturated NaHCO3 (40 mL), and brine (40 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by reversed phase flash chromatography (C18 SiO2, eluted with gradient of MeOH in water+0.05% TFA) affording the desired intermediate (553 mg, 46% yield) as a colorless oil. The purified oil (553 mg, 1.37 mmol) was dissolved in DCM (5 mL) and treated with TFA (1 mL) for 3 h at room temperature, and then the reaction mixture was concentrated under reduced pressure. The residue was dried under high vacuum yielding desired PEG4-mono-methacrylamide 43-1 (750 mg, quant., TFA salt) as amber oil.

The synthetic route of 811442-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Profusa, Inc.; GAMSEY, Soya; BERNAT, Viachaslau; KUTYAVIN, Alex; CLARY, Jacob William; PRADHAN, Sulolit; (192 pag.)US2018/179233; (2018); A1;,
Amide – Wikipedia,
Amide – 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. 26723-60-4, name is 3-Chloro-6,11-dihydro-5,5-dioxo-11-hydroxy-6-methyldibenzo[c,f][1,2]thiazepine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C14H12ClNO3S

Example 2 S^I-Dichloro-betajH-dihydro-e-methyl-deltajdelta-dioxodibenzoICjfUI^JthiazepineA suspension of compound of Formula III (58.0 g) in dichloromethane (600 ml) is cooled to 0-10 0C, HCI gas is bubbled through the above suspension for 2-4 hour at 0-10 0C. Upon completion of starting material, filter the precipitate and dry the solids obtained until constant weight to provide the title compound in 90-95% yield.

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 26723-60-4.

Reference:
Patent; BIOPHORE INDIA PHARMACEUTICALS PVT. LTD.; RANGISETTY, Jagadeesh, Babu; PULLAGURLA, Manik, Reddy; BHUDETI, Rajesh; WO2010/70667; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 26638-53-9, 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. 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of sodium metal (115 mg, 5.00 mmol) in anhydrous MeOH (5.0 mL) was added ketone 3f (308 mg, 1.00 mmol) and the mixture was heated to 100 °C for 2 h in a sealed pressure vial. The reaction was then cooled to room temperature, diluted with water (10 mL) , and extracted with CH2CI2 (3 x 10 mL) . The combined organics were washed with water (2 x 10 mL) , dried over a^SO^ , and concentrated to yield a yellow crystalline solid. This material was recrystallized from MeOH to yield ketone 3h as white prisms (158 mg, 52percent) . NMR (500 MHz , CDCI3) delta 8.33 (dd, J = 8.1, 1.6 Hz, 1H) , 8.04 (d, J = 8.7 Hz, 1H) , 7.63 (ddd, J = 8.0, 7.3, 1.7 Hz, 1H) , 7.46 (d, J = 2.6 Hz, 1H) , 7.42 – 7.34 (m, 2H) , 7.18 (dd, J = 8.7, 2.6 Hz, 1H) , 3.96 (s, 3H) , 3.33 (s, 3H) ; 13C NMR (126 MHz, CDC13) delta 189.0, 162.8, 141.2, 139.1, 134.6, 134.5, 132.4, 128.3, 126.6, 125.5, 118.9, 110.8, 56.3, 39.4; LR-MS calcd. for CisHnlTC S [M+H]+ 304.06, found 303.91

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew C.; HENKE, Adam; GASSAWAY, Madalee M.; RIVERS, Marie-laure; JAVITCH, Jonathan A.; SAMES, Dalibor; WO2015/138791; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics