Month: August 2021

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

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. 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

To a 500 ml three-mouth bottle by adding 200 ml of THF, cooling to 5 C the following add 17.3g (0.46mol, 4 . 0eq) of lithium aluminum hydride, then lower the temperature to the -5 C the following, the three aluminum chloride 3.0g (0.023mol, 0 . 2eq) THF slowly dropwise to the reaction in the solution, stirring for 10 min, temperature at 5 C the following starting to drop plus step amide 19.0g (0.114mol, 1 . 0eq) in 100 ml of solution THF. Added after stirring overnight TLC inspection reaction end, cooling to 0 C the following, starting the dropping water filtration, the filter cake is washed with dichloromethane eluviation, concentrated filtrate, vacuum distillation, to obtain colorless oily liquid 12.0g product. Yield: 71.0%, GC: 99.9%

The synthetic route of 6331-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shao Yuan Science and Technology (Shanghai) Co., Ltd.; Wu, Yong; Lei, Ting jun; Qi, Ming; (12 pag.)CN105461659; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 16066-84-5 as follows. Recommanded Product: 16066-84-5

To a solution of tert-butyl-N-methylcarbamate (3.00 g, 22.9 mmol) in THF (50 mL) was added NaH (1 .37 g, 34.3 mmol) in portions at 0 C. The reaction mixture was stirred at 15 C for an hour. Then 81 (5.24 g, 22.9 mmol) in THF (20 mL) was added dropwise. The reaction mixture was stirred at 15 C for 13 h. The reaction was quenched by ice water (10 mL) slowly and then extracted with EtOAc (20 mL x 3). The combined organic phase was washed with brine (10 mL x 2), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified via silica gel columnchromatography (petroleum ether/ethyl acetate = 4:1) to give 82 (2.9 g, 45%) as a colorless oil.1H N R (400 MHz, CDCI3) 7.95-7.91 (m, 2H), 7.42-7.38 (m, 2H), 4.45 (s, 2H), 3.91 (s, 3H), 2.85 (s, 3H), 1 .48 (s, 9H). To a solution of 82 (2.8 g , 10 mmol) in THF (20 mL) was added LiAIH4(456 mg , 12.0 mmol) in portions at 0 C. The mixture was stirred at 15 C for 2 hours. The mixture was cooled to 0 C and quenched by saturated solution of potassium sodium tartrate (0.5 mL), the mixture was concentrated in vacuum (40C) to give 83 (1 .8 g, 71 %) as a colorless oil.1H NMR (400 MHz, CDCI3) 7.32-7.29 (m, 2H), 7.27-7.23 (m, 1 H), 7.15-7.14 (m, 1 H), 4.68 (s, 2H), 4.42 (s, 2H), 2.82 (s, 3H), 1 .48 (s, 9H). To a solution of 83 (1 .5 g, 6.0 mmol) in DCM (20 mL) was added A/-Fmoc-(S)-valine (2.23 g, 6.57 mmol), DCC (1 .6 g, 7.8 mmol) and DMAP (73 mg, 0.60 mmol). The mixture was stirred at 15 C for 12 h. Then DCM (10 mL) was added and the organic layer was washed with brine (10 mL x 3), dried over Na2S04and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate = 4: 1) to give 84 (1 .8 g, 53%) as a colorless oil.1H NMR (400 MHz, CDCI3) 7.70-7.80 (m, 2H), 7.54-7.62 (m, 2H), 7.35-7.42 (m, 2H), 7.23-7.33 (m, 4H), 7.19 (br s, 2H), 5.34-5.32 (m, 1 H), 5.29-5.14 (m, 2H), 4.43-4.41 (m, 4H), 4.40-4.14 (m, 4H), 2.83 (s, 3H), 2.12-2.23 (m, 1 H), 1 .47 (s, 9H), 0.86 (dd, J – 6.84, 2.87 Hz, 6H). To a solution of 84 (1 .00 g, 1 .75 mmol) in THF (6 mL) was added piperidine (298 mg, 3.50 mmol). The mixture was stirred at 15 C for 12 h . The mixture was concentrated in reduced pressure at 40 C. The residue was purified by column chromatography (petroleum ether/ethyl acetate = 1 :4) to give 85 (400 mg, 65%) as a colorless oil.1H NMR (400 MHz, DMSO-d6) 7.37-7.35 (m, 1 H), 7.34-7.29 (m, 1 H), 7.27-7.22 (m, 1 H), 7.18-7.17 (m, 1 H), 5.16-5.06 (m, 2H), 4.37 (s, 2H), 3.15 (d, J – 4.0 Hz, 1 H), 2.74 (s, 3H), 1 .99-1 .84 (m, 1 H), 1 .42-1 .39 (m, 9H), 0.85 (d , J = 6.8 Hz, 3H), 0.79 (s, J = 6.4 Hz, 3H). To a solution of Acid-04 (164 mg, 0.856 mmol) in DMF (3 mL) was added HATU (390 mg, 1 .03 mmol) and TEA (260 mg, 2.57 mmol). The mixture was stirred at 20 C for 1 h. Then 85 (300 mg, 0.856 mmol) was added in one portion. The mixture was stirred at 20 C for 1 1 h. The reaction was quenched by water (10 mL) slowly at 0 C and then extracted with EtOAc (10 mL x 3). The combined organic phase was washed with brine (10 mL x 1), dried over anhydrous Na2S04, filtered and then HCI/EtOAc (4 M, 4 mL) was added. The mixture was stirred at 20 C for 12 h. The mixture was concentrated in vacuo. The residue was purified by prep. HPLC (column: Luna C18 100 x 30 mm; liquid phase: 0.1 %TFA-ACN; B%: 10%-40%, 12 min). After prep. HPLC, 3N HCI (2 mL) was added before freeze drying. 6-122 (137 mg, 33%) was obtained as an off white solid.1H N R (400 MHz, DMSO-cfe) 9.21 (br s, 2H), 9.03 (s, 1 H), 8.59 (d, J – 8.0 Hz, 1 H), 7.55-7.51 (m, 2H), 7.46-7.45 (m, 2H), 7.35 (d, J – 8.0 Hz, 1 H), 7.24 (d, J – 8.0 Hz, 1 H), 5.19 (s, 2H), 4.97 (s, 2H), 4.37 (t, J – 8.0 Hz 1 H), 4.10 (s, 2H), 2.39 (s, 3H), 2.21 -2.16 (m, 1 H), 0.96 (d, J = 6.0 Hz, 6H); ESI-MS m/z 425 [M+H]+; HPLC purity: 94.93% (220 nm), 87.86% (254 nm).

According to the analysis of related databases, 16066-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 621-38-5, name is 3-Bromoacetanilide, 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. Recommanded Product: 3-Bromoacetanilide

General procedure: A mixture of Acetylaniline (0.2 mmol), NCS (0.26 mmol), D-CSA (0.1 mmol) and 1,3-di(1-adamantl)imidazolium tetrafluoroborate (0.01 mmol) in dioxane (1 mL) wasstirred at room temperature (25 oC) under air atmosphere for 24h. The reactionmonitored by GC-MS. When the acetylaniline was consumed completely, the reactionmixture was quenched with saturated aq. NaHCO3 (4 mL). The resulting mixture wasextracted with EtOAc (4 mL x 3). The organic layer was washed with pure water (4ml x 3). The combined organic layer was dried over anhydrous Na2SO4, filtered andthe solvent was removed under reduced pressure to provide the crude product. Thepurification was performed by flash column chromatography on silica gel.

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

Reference:
Article; Chen, Jie; Xiong, Xiaoyu; Chen, Zenghua; Huang, Jianhui; Synlett; vol. 26; 20; (2015); p. 2831 – 2834;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics