Month: March 2021

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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., Recommanded Product: 630-22-8

To a solution of 2-propen-1 -yl [2-fluoro-3-(4-pyridinylacetyl)phenyl]carbamate (2.2 g, 7.00 mmol) in Lambda/,/V-dimethylacetamide (DMA) (25 ml_) was added N- bromosuccinimide (NBS) (1 .495 g, 8.40 mmol) at 0 C. The reaction mixture was stirred at room temperature for 1 h. 2,2-Dimethylpropanethioamide (0.985 g, 8.40 mmol) was added at room temperature and the mixture was stirred at 60 C for 1 .5 h. The reaction mixture was quenched with water and ethyl acetate. The organic layer was separated, washed with water, dried over MgSO4, filtered and evaporated. The red oil was purified by flash column chromatography on silica gel (100 % EtOAc). 2-Propen-1 -yl {3-[2- (1 ,1 -dimethylethyl)-5-(4-pyridinyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}carbamate (200 mg, 0.486 mmol, 6.94 % yield) was isolated as white foam. 1 H NMR (400 MHz, DMSO-c/e) ppm 1 .46 (s, 9 H) 4.58 (dt, J=5.31 , 1 .39 Hz, 2 H) 5.22 (dd, J=10.48, 1 .64 Hz, 1 H) 5.34 (dd, J=17.18, 1 .77 Hz, 1 H) 5.84 – 6.04 (m, 1 H) 7.13 – 7.29 (m, 4 H) 7.66 – 7.84 (m, 1 H) 8.40 – 8.57 (m, 2 H) 9.46 (s, 1 H); HPLC Rt= 2.95 min, MS (ESI): 412.1 [M+H]+.

The synthetic route of 630-22-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141761-83-3,Some common heterocyclic compound, 141761-83-3, name is Methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate, molecular formula is C11H10ClNO4, 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.

500ml three bottles,After adding 150 ml of water and 12 g (0.3 mol) of sodium hydroxide, the mixture was stirred until the solid was completely dissolved, and 100 ml of ethanol was further added thereto. The temperature was lowered to 20C, 6-chloro-4-methyl-3,4-dihydro- (0.1 mol) of methyl 2,4-benzoxazin-8-carboxylate was added and stirred for 3 h. After the reaction was completed, the reaction mixture was cooled to 10 C or less, diluted hydrochloric acid was adjusted to pH 2, filtered and dried to give 4-methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid as an off-white solid, 21.9 g, 91% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate, its application will become more common.

Reference:
Patent; Yangtze River Pharmaceutical Group Sichuan Hairong Pharmaceutical Co., Ltd; Li, Yuanbo; Xie, Yipeng; Cao, Kangping; Wang, Qiang; Wu, Puhua; Wang, Ying; Zhou, Xinyu; (9 pag.)CN104557907; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 116861-31-5, A common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, molecular formula is C8H16ClNO2, 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 l-(lR-pyrrolo[2,3-c]pyridin-2No.yl)ethanone oxime (Example 72) (100 mg, 0.42 mmol) and sodium hydride (18 mg of a 60% in mineral oil, 0.45 mmol) in N,N- dimethyl formamide (4 mL) was stirred for 0.5 h. N-Boc chloropropylamine (86 mg, 0.44 mmol) was added dropwise and the reaction mixture was heated at 60C for 3 h. After stirring at room temperature for 12 h, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (3 15 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated to an oil. Purification by Biotage chromatography (30 to 100% ethyl acetate in hexanes) produced tert-butyl 3- [[[phenyl(1H-pyrrolo[2,3-c]pyridin-2- yl) methylene]amino]oxy]propylcarbamate (76 mg, 46%) as a white solid: mp 52-58C; ESI MS m/z 395 [C22H26N403 + H]+; HPLC (Method A) 98.6% (AUC) , tR = 19.2 min.

The synthetic route of 116861-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/97129; (2005); A2;,
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. 711007-44-2, name is 2,3-Diaminobenzamide, A new synthetic method of this compound is introduced below., SDS of cas: 711007-44-2

Example 1: Benzyl 3-(4-carbamoyl-lH-benzo[d]imidazol-2-yl)-3,4-dihydroisoquinoline-2- (lH)-carboxylate.[00147] Step-1: To a solution of 2-((benzyloxy)carbonyl)-l,2,3,4-tetrahydroisoquinoline-3- carboxylic acid (1.0 g, 3.21 mmol) in anhydrous DMF (20 ml) was added EDCHCl (1.85 g, 9.63 mmol), HOBt (681 mg, 5.05 mmol) and triethylamine (0.7 ml, 4.81 mmol) and the mixture was stirred at RT for 10 min. To this reaction mixture, 2,3-diaminobenzamide (606 mg, 4.01 mmol) was added and was stirred at RT over night. The reaction was poured in to water, stirred for 30 min and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate and concentrated under vacuum to yield benzyl 3-(2-amino-3- carbomoylphenylcarbamoyl)-3,4-dihydroisoquinoline-2(lH)-carboxylate. MS (ES+): m/z 445.1 [M+H]+

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; LIM, Dong, Sung; SMITH, David, E.; WO2011/2520; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 104863-65-2, 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. 104863-65-2, name is N-Methoxy-N-methylpropionamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 1.4. General method E: Synthesis of Intermediate Gen-8 Gen-7 Gen-8 Gen General method A solution of LDA is prepared by adding dropwise a 2.5 M butyllithium solution in hexane (1.1 to 1.2 eq.) to a solution of DIPA (1.07 to 1.2 eq.) in THF under nitrogen at a temperature comprised between -78C and -5C. The reaction mixture is stirred 15 min to 30 min at the same temperature. Then Intermediate Gen-6-a (1 to 1.2 eq.) in THF is added dropwise between -78C and -60C, and the reaction is stirred under nitrogen at -78C for 1 h to 1.33 h. Then Intermediate Gen-7 (1.1 to 1.2 eq.) is added dropwise or portionwise by monitoring the temperature. The mixture is stirred 1.5 h to 3 h between -78C and -70C and quenched with a saturated aqueous NH4C1 solution. EtOAc is added, then the organic layer is separated, dried over Na2S04, filtered and evaporated to dryness. The residue is purified by chromatography of silica gel to give Intermediate Gen-8.

The chemical industry reduces the impact on the environment during synthesis N-Methoxy-N-methylpropionamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALAPAGOS NV; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BEAUMONT, Stephane Nicolas Alain; BONNATERRE, Florence Marie-Emilie; WO2015/24905; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 40545-33-3, name is 2-Amino-5-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 40545-33-3, SDS of cas: 40545-33-3

General procedure: To a cold (0-5 C) stirred suspension of aminobenzamides 2a-g (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate cinnamoyl chloride 3a-e, 3-phenylpropioloyl chloride 3f-k and 3-phenylpropanoyl chloride 3l-o was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from the appropriate solvent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-5-methylbenzamide, and friends who are interested can also refer to it.

Reference:
Article; Raffa, Demetrio; Maggio, Benedetta; Raimondi, Maria Valeria; Cusimano, Maria Grazia; Amico, Giandomenico; Carollo, Anna; Conaldi, Pier Giulio; Bai, Ruoli; Hamel, Ernest; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 427 – 435;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 14437-03-7,Some common heterocyclic compound, 14437-03-7, name is Methyl tosylcarbamate, molecular formula is C9H11NO4S, 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: The 4-substituted methyl (phenylsulfonyl)carbamate was dissolved in the chosen alcohol (2 mL) in a microwave vial, which was closed using an aluminum open-top seal with PTFE-faced septum. The reaction mixture was heated under microwave irradiation at 100-120 oC for 20-60 min. The crude reaction mixture was concentrated under reduced pressure and the residue was purified using silica gel column chromatography to yield the desired (aryl)carbamate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl tosylcarbamate, its application will become more common.

Reference:
Article; Isaksson, Rebecka; Kumpi?a, Ilze; Larhed, Mats; Wannberg, Johan; Tetrahedron Letters; vol. 57; 13; (2016); p. 1476 – 1478;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 563-83-7, name is Isobutyramide, 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 Isobutyramide

A suspension of Example B7 (0.077 g, 0.888 mmol) in DCE (5.5 mL) was treated with oxalyl chloride (0.078 mL, 0.888 mmol), stirred at RT for 1 h, warmed to 80 C. for 1.5 h, cooled to RT, added drop-wise to a solution of 5-((2-(1-(trideuteromethyl)-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.200 g, 0.740 mmol) and pyridine (0.299 mL, 3.70 mmol) in THF (8 mL) and stirred at RT overnight. The mixture was treated with satd. Na2CO3, extracted with EtOAc (6*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was dissolved in MeCN/H2O, frozen and lyophilized to afford N-((5-((2-(1-(trideuteromethyl)-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)isobutyramide (199 mg, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.10 (s, 1H), 10.84 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.25-8.24 (m, 2H), 8.07 (d, J=9.0 Hz, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 6.69 (dd, J=5.7, 2.4 Hz, 1H), 2.66 (m, 1H), 1.08 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 384.2 (M+H+).

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

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 676371-64-5, 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. 676371-64-5, name is Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of Compound II- 10-1 : To a solution of II-3-1 (300 mg, 1.24 mmol) in DMF (l5mL) was added NaH (210 mg, 2.5 mmol) at 0 C. The reaction mixture was stirred at the same temperature for 20 min before iodomethane (50 mg, 2.5 mmol) was added. The resulting mixture was stirred at room temperature for 3h before water was added. The reaction mixture was extracted with ethyl acetate. The combined organic layer was concentrated to dryness. The residue was purified by silica gel column (pet. ether/EtOAc=5: 1) to give II-10-1 (310 mg, yield: 97%) as a colorless oil.

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, Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KURA ONCOLOGY, INC.; BURROWS, Francis; (275 pag.)WO2020/69027; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 744183-20-8, name is tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H22N2O2, 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: tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

A solution of 5,7-dichloro-3-iodo-1,6-naphthyridine (7.0 g, 21.6 mol), DIPEA (5.6 g, 43.2 mmol) and tert-butyl (1R,3s,55)-3-amino-8-azabicyclo[3 .2.11 octane-8-carboxylate(5.8 g, 25.9 mmol) dissolved in NMP (70 mL) was heated at 110C for 3 h. The reaction mixture was purified by column chromatography (eluted with EtOAc:petroleum ether 0- 20 %) to give the title intermediate as ayellow solid (10.2 g, 91.8 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 744183-20-8, its application will become more common.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics