Month: August 2021

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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

The N – (4 – fluoro -2 – methoxy -5 – nitro – phenyl) -4 – (6 – methoxy -1 – methyl – 1H – indole -3 – yl) pyrimidine -2 – amine (3 d) (0.42 g, 1.0 mmol) dissolved in tetrahydrofuran (30 ml), is added sodium hydride (0.04 g, 2.0 mmol, w/w=60%), stir at room temperature 30 minutes, add (1 – hydroxy methyl propyl) – tert-butoxycarbonyl amino (0.23 g, 1.5 mmol), continuing stirring at room temperature 5 hours. The addition of water (10 ml) quenching the reaction, concentrated under reduced pressure to remove most of the tetrahydrofuran, is added to the residue in methylene chloride (100 ml), water (50 ml), layered, aqueous phase methylene chloride (100 ml) extraction, the combined organic phase, saturated salt water (50 ml) washing, drying with anhydrous sodium sulfate, concentrated under reduced pressure, to obtain a yellow solid N – [1 – [[5 – methoxy -4 – [[4 – (6 – methoxy -1 – methyl – indole -3 – yl) pyrimidine -2 – yl] amino] -2 – nitro – phenoxy] methyl] cyclopropane alkyl] tert-butyl carbamate (3 e) (0.59 g).

According to the analysis of related databases, 107017-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Li Yao; Zhang Guobiao; Hu Shihong; Wei Yonggang; (22 pag.)CN108530428; (2018); A;,
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Application of 20188-40-3, A common heterocyclic compound, 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, molecular formula is C8H11ClN2O, 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 ethyl 2-(bromomethyl)-6-(2-fluoro-4-(trifluoromethyl)phenoxy)benzoate (0.21 g) obtained in Reference Example 328 in ethanol (2 mL) were added 4-(aminomethyl)benzamide hydrochloride (0.11 g) and potassium carbonate (0.14 g), and the mixture was stirred at 45°C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and the obtained solid was recrystallized from ethyl acetate-ethanol. The obtained crystals were collected by filtration and dried to give the title compound (0.055 g). MS: [M+H]+ 445.1 1H NMR (300 MHz, DMSO-d6) delta 4.42 (2H, s), 4.68 (2H, s), 7.04 (1H, t, J = 8.4 Hz), 7.15 (1H, d, J = 7.9 Hz), 7.31 (3H, d, J = 8.1 Hz), 7.46 (1H, d, J = 7.6 Hz), 7.51 (1H, d, J = 8.5 Hz), 7.62-7.69 (1H, m), 7.81-7.96 (4H, m).

The synthetic route of 20188-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
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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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1,4-Diazepan-1-yl)ethanone

A solution of lambda/-(7-chloro-2-methylpyrazolo[l,5-alpha]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol) and l-(l,4-diazepan-l-yl)ethanone (101 mg, 0.75 mmol) in DMF (1.0 mL) was stirred at 100 0C for 2h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (25-40% MeCN/H2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (87.7 mg, 78%). 1H NMR (DMSO-de) [1 :1 ratio of rotamers: delta: 10.93 (s, IH); 10.91 (s, IH)], 7.99 (d, J = 8.3 Hz, 2H), 7.62 (dd, 2H), [1 :1 ratio of rotamers: 7.13 (s, IH); 7.07 (s, IH)], [1 :1 ratio of rotamers: 6.19 (s, IH); 6.18 (s, IH)], [1 :1 ratio of rotamers: 4.37 (t, J = 5.6 Hz, 2H); 4.20 (t, J = 5.4 Hz, 2H)], [1 :1 ratio of rotamers: 4.03 (t, J = 5.6 Hz, 2H); 3.97 (t, J = 5.9 Hz, 2H)], 3.63 – 3.78 (m, 2H), [1 :1 ratio of rotamers: 3.58 (t, J = 5.9 Hz, 2H); 3.52 (t, J = 5.8 Hz, 2H)], 2.37 (s, 3H), [1 :1 ratio of rotamers: 2.03 – 2.11 (m, 2H); 1.94 (quin, J = 5.9 Hz, 2H)], [1 :1 ratio of rotamers: 2.02 (s, 3H); 1.89 (s, 3H)], 1.46 (s, 6H); ESI-MS: m/z 451.3 (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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/123986; (2009); A1;,
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 874823-37-7 as follows. Recommanded Product: 874823-37-7

Example 45 N4-[(trans-4-aminocyclohexyl)methyl]-5-bromo-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine 5-Bromo-2,4-dichloropyrimidine (1.1 g, 4.83 mmol) was dissolved in DMA (25 mL). To this solution was added tert-butyl-trans-4-aminomethylcyclohexylcarbamate hydrochloride (1.54 g, 5.80 mmol), followed by DIEA (1.98 mL, 11.4 mmol). The reaction was stirred at 25 C. for 18 h. The reaction was worked up by removal of the volatiles in vacuo. The crude was purified via flash chromatography (SiO2, 10-25% EtOAc-Hexanes) to afford 1.32 g (65%) of {4-[(5-bromo-2-chloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester.

According to the analysis of related databases, 874823-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2-chloro-N-isopropylacetamide (602 mg, 4.44 mmol) and methyl 4-hydroxybenzoate (500 mg, 3.29 mmol) in DMF (18 mL) at r.t. under N2 was added potassium carbonate (1817 mg, 13.15 mmol) in a single portion. The mixture was heated at 80 ^C overnight, cooled and partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organics were washed with H2O and brine, dried (phase sep.) and concentrated to give crude methyl 4-[2-(isopropylamino)-2-oxo- ethoxy]benzoate (870 mg, 3.18 mmol, 97% yield). LC-MS (ES+, Method C): 2.32 min, m/z 252.0 [M+H]+

The chemical industry reduces the impact on the environment during synthesis N-Isopropyl-2-chloroacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
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Synthetic Route of 3984-14-3, A common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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 2,4,5-trifluorobenzoic acid (5 g, 28.4 mmol) in dichloromethane (50 ml_) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.53 g, 42.6 mmol) and triethylamine (8.64 g, 1 1 .9 ml_, 85.2 mmol). After 15 minutes N,N-dimethylsulfamide (5.3 g, 56.8 mmol) was added followed by 4-dimethylaminopyridine (347 mg, 2.8 mmol). The resulting mixture was allowed to stir at room temperature for 18 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate (50 ml_) and 2M HCI (150 ml_). The aqueous phase was separated and extracted with ethyl acetate (2 x 50 ml_). The combined organic extracts were dried over magnesium sulfate, filtered, evaporated and the residue purified by reverse-phase chromatography using a gradient of acetonitrile + 0.1 % formic acid to 100% acetonitrile to yield the title compound (993 mg, 31 %) as a white solid. 1H NMR (400 MHz, CDCI3): delta 3.02 (s, 6H), 7.08 (dd, 1 H), 7.92 (dd, 1 H), 8.60-8.80 (br s, 1 H). LCMS Rt = 2.60 minutes MS m/z 281 [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; PFIZER LIMITED; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2013/88315; (2013); A1;,
Amide – Wikipedia,
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Related Products of 597563-17-2, These common heterocyclic compound, 597563-17-2, name is tert-Butyl (1-(3-bromophenyl)cyclopropyl)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.

EXAMPLE 106; Step 1; Epoxide opening with 1- (3-bromophenyl) cyclopropyl amine; N-BOC-1- (3-bromophenyl) aminocyclopropane (15.60g, 50.2 mmol) was treated with 4N HC1 in dioxane (50 mL) and stirred for 2 h. The volatiles were evaporated in vacuo and the residue taken up into 1N NaOH (250 mL). The mixture was extracted with diethyl ether (2 X 200 mL). The combined ether extracts were washed with brine (50 mL), dried (sodium sulfate), then filtered and evaporated in vacuo to provide the amine free base. The amine free base was dissolved in 2-propanol (250 mL) and the epoxide (15. 0g, 50.2 mmol) was added. The mixture was heated to reflux for 22 h and allowed to stand at ambient temperature for 3 d. Analysis by HPLC indicated that the desired product predominated, and that some starting cyclopropylamine remained unreacted. The starting epoxide was consumed. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (eluted 2: 1 hexane/ethyl acetate) to provide the final product (13.68 g, 53%).

The synthetic route of 597563-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 744183-20-8, The chemical industry reduces the impact on the environment during synthesis 744183-20-8, name is tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, I believe this compound will play a more active role in future production and life.

To a mixture of the product of the previous step (1020 mg, 3.42 mmol) and tert25 butyl (1R,3s,55)-3-amino-8-azabicyclo[3.2.ljoctane-8-carboxylate (774 mg, 3.42 mmol)in DMSO (34.3 mL) was added DIPEA (1.787 mL, 10.26 mmol) at RT. The resultingmixture was stirred at 120 C for 19 h. Solvent was removed by rotary evaporation to give cmde product, which was purified by column chromatography to give the titlecompound as a brown solid (513 mg, 30.7% yield). (m/z): [M+Hj calcd for C25H34C1N503 488.24 found 488.2.

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 exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, other downstream synthetic routes, hurry up and to see.

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,
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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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1,1-Trifluoro-N-phenylmethanesulfonamide

tert-Butyl 4-{ [(trifluoromethyl)sulfonyl] oxy}-3,6-dihydropyridine-l(2H)-carboxylateDi-wo-propylamine (22 ml) was dissolved in dry THF (125 ml) and cooled to -78C. «-Butyllithium (62.5 ml, 2.5M) was added dropwise. The solution was stirred for 15 minutes, then tert-bntyl 4-oxopiperidine-l-carboxylate (28.32 g) in THF (100 ml) was added dropwise. The reaction mixture was stirred for 1 hour at -78C, then N- phenyltrifluoromethanesulfonimide (53.8 g) in THF (150 ml) was added dropwise. The reaction mixture was stirred at -78C for 2 hours and allowed to warm up to room temperature and stirred overnight. The reaction mixture was then concentrated in vacuo and the residue dissolved in ether (1000 ml). This was washed with water (500 ml), 2M sodium hydroxide solution (3 x 500 ml), water (500 ml) and brine (500 ml) then dried over magnesium sulfate and concentrated to give the title compound as a pale brown oil (45.38 g, 96%) which was used without further purification; 1H NMR (CDCl3) deltal.48 (9H, s), 2.44 (2H, m), 3.63 (2H, t), 4.00 (2H, q), 5.70 (IH, br m).

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 456-64-4.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/60408; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 4793-24-2,Some common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, molecular formula is C7H5ClFNO4S, 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 2-chloro-4-fluoro-5-sulfamoylbenzoic acid (3.2 g, 12.65 mmol) in THF (10 mL) was added IM BH3 THF (38 mL, 38.0 mmol). After stirring 12h, the reaction mixture was quenched with MeOH and concentrated in vacuo. The residue was purified by chromatography (silica, EtO Ac-Hex) to afford 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.9 g). To a suspension of 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.78 g, 7.43 mmol) in DCM (10 mL) was added PBr3 (2.2 Ig, 8.17 mmol). The reaction was stirred for 24 h when it was determined to be complete by GCMS. The reaction was carefully quenched with H2O and then partitioned between THF and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 5-(bromomethyl)-4-chloro-2-fluorobenzenesulfonamide (1.98 g) as an off-white solid. 1H-NMR (DMSO-J6, 400 MHz) delta 8.08 (d, J = 7.8 Hz, IH), 7.84 (s, 2H), 7.80 (d, J = 9.9 Hz, IH), 4.83 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics