Amides-buliding-blocks

Electric Literature of 337463-88-4, 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 337463-88-4 as follows.

The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with water and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHC13) to afford a solid (2. 5g, 38%). MS (+ve ion electrospray) m/z 253 (MH+).

According to the analysis of related databases, 337463-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/2490; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 7160-22-7, These common heterocyclic compound, 7160-22-7, name is N-(3,4-Dichlorophenyl)pivalamide, 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.

2b) Preparation of Compound 2; A solution of Compound 1 (50 g) in tetrahydrofuran (300 mL) was cooled to-50 – -4O0C under an inert atmosphere of nitrogen. N-Butyl lithium (2.5M in hexanes, 179 mL) was added at such a rate as to keep the solution’s internal temperature between -45 – -30 0C (ca. 15 – 30 min addition). The solution was held at ca. -35 – -25 0C until HPLC indicated that the initial reaction was complete. The solution was then recooled to – 45 – 4O0C, and sulfur dioxide (-16.9 g) was bubbled through the solution, keeping the internal temperature below approximately -14 0C, until the solution was acidic. When the reaction was complete, the mixture was warmed to -10 – 0 0C. Starting at -2 – 3 0C, sulfuryl chloride (25.2 mL) was then added dropwise to the tetrahydrofuran solution over 5 – 15 min, keeping the temperature below approximately 22 0C. After 5 min, HPLC confirmed reaction completion, while the solution was kept around 10 – 15 0C. The mixture was solvent-exchanged into alpha,alpha,alpha-trifluorotoluene under reduced pressure, filtered, partially concentrated under vacuum (to -100 mL), followed by addition of dichloromethane (350 mL). To this mixture was added a solution of piperazine (61.2 g) in dichloromethane (625 mL) at ambient temperature dropwise, keeping the solution’s internal temperature at 15 – 27 0C (2h addition). The reaction was held at 20 – 24 0C until complete. The mixture was washed with deionized water (200 mL), the organic layer concentrated, followed by addition of heptane (450 mL). The product (70.5 g) was isolated by filtration, washed with heptane (50-100 mL), and dried under vacuum at 50-55 0C.

The synthetic route of 7160-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39091; (2009); A1;,
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

Electric Literature of 85006-25-3, 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. 85006-25-3 name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, 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.

Preparation 2 [tert-Butoxycarbonyl-[(4-methoxyphenyl)methyl]amino] tert-butyl carbonate A 20 L reactor, under nitrogen is charged with (tert-butoxycarbonylamino) tert- butyl carbonate (812.9 g, 3.48 mol), dimethylformamide (4.4 L), potassium carbonate (626.5 g, 4.52 mol) and l -(chloromethyl)-4-methoxy -benzene (462 mL, 2.56 mol). The mixture is stirred at 40 C overnight. lH NMR analysis shows incomplete reaction. Additional potassium carbonate (626.5 g, 4.52 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after 48 hours shows the reaction is still incomplete. Additional potassium carbonate (482 g, 3.49 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after overnight reaction shows complete reaction with no starting materials remaining. Water (5 L) and MTBE (5 L) are added and the layers are separated. The organic layer is washed with water (3×3 L), dried over sodium sulphate, and concentrated to give the title compound (1.21 Kg, 98%). 1H NMR (d6-DMSO) delta 7.20 (d, J= 8.3 Hz, 2H), 6.91 (d, J= 8.3 Hz, 2H), 3.73 (s, 2H), 3.35 (s, 3H), 1.41 (s, 18H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (tert-butoxycarbonyl)oxycarbamate, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; MARTIN, Fionna Mitchell; WO2015/138208; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 207405-60-5, These common heterocyclic compound, 207405-60-5, name is tert-Butyl 5-hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylate, 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.

Preparation of 2-Aza-2-(t-butoxycarbonyl)bicyclo[2.2.1]heptan-5-one STR36 Dimethylsulfoxide (85.9 mmol) was added to a solution of oxalyl chloride (39.5 mmol) in dichloromethane (100 mL) at -78– C. Stirred for 20 minutes whereupon [exo]2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-ol (35.7 mmol) in dichloromethane (50 mL). Stirred at -78– C. for 3 hours then triethylamine (179 mmol) was added to the reaction then warmed to room temperature for one hour. Brine was added then the reaction was extracted with dichloromethane (3*200 mL). The organic extracts were dried over magnesium sulfate then evaporated. The residue was purified by preparative HPLC over silica gel eluding with 10% to 75% ethyl acetate in hexanes to yield 2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-one (31.3 mmol).

The synthetic route of 207405-60-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6124312; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, 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 19047-31-5, Computed Properties of C5H8ClNO

Compound 1d (30 mg, 0.13 mmol) was dissolved in 2 mL of DMF,Potassium carbonate (37.0 mg, 0.27 mmol) was added,80 reaction 30min,Compound 2a (26.8 mg, 0.20 mmol) was added,80 C overnight.After the reaction is over,Cool to room temperature.Add appropriate amount of water,Ethyl acetate was extracted three times,The organic phases were combined and washed with saturated brine,Dried over anhydrous magnesium sulfate,The crude product was distilled under reduced pressure.Separation and purification by column chromatography,A 33.6 mg white solid was obtained.Yield: 78.1%

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, 2-Chloro-N-cyclopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; Chen, Jianzhong; Xie, Xin; Qian, Haiyan; Chen, Lili; Wang, Zhilong; (42 pag.)CN106167497; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 22958-64-1, 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. 22958-64-1 name is 2-(4-Sulfamoylphenyl)acetic acid, 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.

[00361] To a solution of 2-amino-6-(2,2,2-trifluoro-1 -phenylethyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridine-3-carbonitrile (Intermediate Core-2a_D) (60 mg, 0.178 mmol), 2- (4-sulfamoylphenyl)acetic acid Core-2a_6d (60 mg, 0.267 mmol), DIPEA (46 mg, 0.356 mmol) in DMF (10 ml.) was added aq. T3P (50% in EtOAc) (170 mg, 0.267 mmol) at 20 C. The mixture was stirred at 20 C for 1 h. The reaction was concentrated to oil and diluted with EtOAc (10 ml_), washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated to a yellow oil, which was purified by prep-HPLC (base) to get A/-(3-cyano-6-(2,2,2-trifluoro-1 – phenylethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-(4-sulfamoylphenyl)acetamide (18 mg, yield: 18%) as a yellow solid; 1H NMR (400 MHz, CD3OD) d 7.88 (d, =8.41Hz, 2H), 7.37- 7.59 (m, 7H), 4.51 -4.58 (m, 1H), 3.94 (s, 2H), 3.66-3.84 (m, 2H), 3.06-3.19 (m, 1H), 2.78-2.92 (m, 1H), 2.56-2.72 (m, 2H); LC-MS Rt 0.945 min, MS m/z [M+H]+ 535.1, Method 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Sulfamoylphenyl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, 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 177906-48-8, name: trans-N-Boc-1,4-cyclohexanediamine

To a solution of 21.43g (0.1mol) of tert-butyl N-(trans-4-aminocyclohexyl) carbamate in 250mL of N,N-dimethylformamide were added 16.76mL (0.12mol) of bis (2-bromoethyl) ether and 34.85mL (0.25mol) of triethylamine, and the mixture was stirred for 6 hours at 70C. Then solvent was removed under reduced pressure and the residue was treated with ethyl acetate. The organic layer was washed with sodium carbonate aqueous solution and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform alone to chloroform/methanol = 30/1) to give 19.92g (70%) of the title compound.

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, trans-N-Boc-1,4-cyclohexanediamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 7341-96-0, 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 7341-96-0 as follows.

To a cooled (0 C), clear, yellow solution of 4-chloro-3-fluoro-2-(6- methoxypyrimidin-4-yl)aniline (1 g, 3.94 mmol) in ACN (56.3 ml) was added isoamylnitrite (0.79 ml, 5.91 mmol), followed by the dropwise addition of TMSN3 (0.79 ml, 5.91 mmol). After 10 mm, the cold bath was removed, and the reaction was allowed to warm to rt and stirred at rt for lh. Next, propiolamide (0.8 17 g, 11.83 mmol) andCu20 (0.05 6 g, 0.3 94 mmol) were added. After 1 h, the yellow cloudy reaction was diluted with EtOAc, and washed with sat NH4C1, brine, dried over MgSO4, filtered and concentrated to give a yellow solid. DCM (10 ml) was added and the resulting mixture was sonicated. The suspension was filtered and the solid was air-dried. A yellow solid obtained as 1 -(4-chloro-3 -fluoro-2-(6-methoxypyrimidin-4-yl)phenyl)- 1 H- 1,2,3 -triazole25 4-carboxamide (1.003 g, 73.0% yield). MS(ESI) m/z: 349.0 (M+H).

According to the analysis of related databases, 7341-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 116861-31-5, These common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)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.

To a solution of 5-3 (40 mg, 97 pmol) and 19-1-1A (23 mg, 116 pmol) in DMF (300 uL) was added K2CO3 (27 mg, 194 pmol). The mixture was mixture was stirred at room temperature for 16 hr. The reaction cooled and diluted with DCM (5 mL). The solution was filtered and the filtrate was concentrated under reduced pressure. The crude was purified by flash column chromatography (ISCO, silica, l2g, ethyl acetate in hexanes) to afford 15 (18.9 mg, 34% yield).

Statistics shows that tert-Butyl (3-chloropropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 116861-31-5.

Reference:
Patent; TP THERAPEUTICS, INC.; ROGERS, Evan W.; CUI, Jingrong Jean; ZHAI, Dayong; ZHANG, Han; UNG, Jane; DENG, Wei; WHITTEN, Jeffrey; (146 pag.)WO2019/126121; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics