Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, belongs to indolines-derivatives 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 2436-29-5, Safety of 3-(1,3-Dioxoisoindolin-2-yl)propanal

C. 3-Phthalimidopropionaldehyde oxime: The product of Ex. 284, part B (14.0 g, 69.0 mmol) was reacted with hydroxylamine hydrochloride (5.80 g, 83.0 mmol) in pyridine (200 mL). After stirring overnight, the pyridine was evaporated and the resultant mixture diluted with water. The precipitate was collected and dried providing the title product as a white solid (8.00 g, 53%): NMR (CDCl3) delta 7.82 (m, 2H), 7.76 (m, 2H), 6.82 (t, 1H), 3.90 (m 4H).

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, 3-(1,3-Dioxoisoindolin-2-yl)propanal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The DuPont Merck Pharmaceutical Company; US5710159; (1998); A;,
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Related Products of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

(S)-tert-Butyl 4-( 1 -amino- 1 -oxo-3-(4-(4,4,5 ,5 -tetramethyl- 1 ,3 ,2-dioxaborolan-2- yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 300 mg), 6-bromo-2-methylisoindolin-l-one (Example 30, step (i), 131 mg) and potassium acetate (171 mg) in a mixture of acetonitrile (15 mL) and water (5 mL) was stirred under nitrogen at 900C with 1,1 delta(di-fert-butylphosphino)ferrocene palladium dichloride (378 mg). After 4 h the reaction mixture was cooled to room temperature and diluted with water (50 mL). The products were extracted with ethyl acetate (3 x 50 mL) and the combined extracts dried over magnesium sulfate and concentrated to afford the sub-titled compound (200 mg).m/e (MultiMode+) 436 [M+2Eta-BOC]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; METE, Antonio; MATHER, Andrew; MILLICHIP, Ian; WO2010/128324; (2010); A1;,
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Some common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, molecular formula is C11H9NO3, 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: (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

A mixture of (R)-N-(2,3-epoxypropyl)-phthalimide (1.02 g, 5.0 mmol), phenol (5.0 mmol), p-xylene (2 mL) and DBU (0.05 mL) was stirred under N2 at 120 C. for 8 h. After cooling to 80 C. iPrOH (20 mL) and anhydrous hydrazine (1 mL) were added and the mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to RT, 0.5N aq. NaOH (50 mL) was added, extracted with EtOAc (100 mL). Extract was washed with 0.5N aq. NaOH (50 mL), brine (50 mL), dried over Na2SO4 and evaporated. The residue was triturated with cold Et2O, the solid was collected by filtration, dried in vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181140-34-1, its application will become more common.

Reference:
Patent; Gregor, Vlad E.; Liu, Yahua; Anikin, Alexey; McGee, Danny Peter Claude; Mikel, Charles; McGrath, Douglas Eric; Vavilala, Goverdhan Reddy; Pickens, Jason C.; Kadushkin, Alexander; Jiang, Luyong; Thiruvazhi, Mohan Santhanam; Zozulya, Sergey; Vairagoundar, Rajendran; Zhu, Tong; Chucholowski, Alexander; Webb, Thomas; Gantla, Vidyasagar Reddy; Yan, Zheng; US2008/171769; (2008); A1;,
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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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C13H16BrNO2

Tert-butyl-5-bromisoindoline-2-carboxylate (20.0 g, 67.09 mmol) was dissolved in Dioxane (200 ml.) and the solution was purged with Argon gas for 10 min. Bispinacalato diborane (34.07 g, 134.18 mmol), KOAc (26.34 g, 268.36 mmol) and Pd(PPh3)4 (7.75 g, 6.70 mmol) were added and the reaction mixture was stirred at 80C for 12 h. Reaction mixture was diluted with water, extracted with EtOAc (1 Ltr. X 2) twice The combined organic layers were washed with water (500 ml_), brine (300 ml_), dried over sodium sulphate and concentrated under vacuo. Crude compound was purified by Combiflash chromatography using 40 g Column and 10% EtOAc in n-Hexane to afford title compound as a White solid 23.0 g (99.30 %). Rf = 0.50 (10% EtOAc in n-Hexane); 1 H NMR (300 MHz, CDCI3): d 7.72-7.65 (m, 2H), 7.31 -7.20 (m, 1 H), 4.70-4.60 (m, 4H), 1 .40 (s, 9 H), 1 .37 (s, 12H).

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 201940-08-1.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; NG, Shuyi Pearly; RAO, Srinivasa P S; (126 pag.)WO2019/244049; (2019); 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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

General procedure: To a solution of compound 3 (1.0 mmol) and substituted isatin (1.0 mmol) in ethanol, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.0 mmol) was added. The reaction mixture was stirred at room temperature for about 1 h. The solvent was removed and CH2Cl2 was added, the organic phase was washed with water and brine, dried over Na2SO4. After removal of the solvent, the residue was purified by silica gel chromatography using acetone/petroleum ether (1/2) as the eluent to give the corresponding steroidal pyran?oxindole hybrids.

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:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Shan, Li-Hong; Yu, De-Quan; Liu, Hong-Min; Steroids; vol. 88; (2014); p. 44 – 52;,
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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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C11H9NO3

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use.1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
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Reference of 181140-34-1, These common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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 243.9 g (1.20 mol) of S – (+) – N- (2,3-ethoxypropyl) phthalimide (SM1), 121.8 g (800.30 mmol)2- (4-aminophenylamino) ethanol was added to 3L three-necked flask in turn, then 2.0L of anhydrous ethanol was added, and the temperature was raised at 75-85C for 24 h. With tap water to 40 ~ 45 , filter, washed with ethanol, filter cake, white solid. And dried at 50 to 60 C under reduced pressure for 5 hours. To give 256.0 g of compound I in a yield of 90.0%.

Statistics shows that (R)-(-)-N-(2,3-Epoxypropyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 181140-34-1.

Reference:
Patent; Chongqing Zhien Pharmaceutical Co., Ltd.; Deng Xianglin; Li Daming; Huang Chaoming; Huang Minghui; Feng Yongmei; Wang Fei; Liao Xingting; (29 pag.)CN106432218; (2017); A;,
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Some common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. Product Details of 70478-63-6

Step a. To a solution of 4-bromoisoindoline-l,3-dione (CAS Number 70478-63-6, 15.00 g, 66.4 mmol) in DCM (150 ml) was dropwise added methyl magnesium bromide (1 M in THF) (199 ml, 199 mmol) at 0¡ãC under N2 atmosphere. The reaction mixture was stirred at rt for 2 h. The reaction mixture was combined with three other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured in to NH4C1 solution (500 ml) and extracted with the DCM (3 x 1 L). The combined organic phases was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (30-32 percent EtOAc in hexane) yielding a mixture of 7-bromo-3-hydroxy-3-methylisoindolin-1-one and 4-bromo-3-hydroxy- 3-methylisoindolin-1-one (37.00 g, 153.6 mmol). LCMS: Method A, 1.435 min, MS: ES+ 242.33, 244.33.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 70478-63-6, its application will become more common.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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Application of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(m-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(m-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5k): Melting point 285-287 C; white solid, 94%;1H-NMR (CDCl3, 400 MHz): delta/ppm 4.99 (d, J = 14.64 Hz, 1H), 4.68-4.71 (m, 1H), 4.39 (d, J = 10.24 Hz, 1H), 3.85 (d, J = 13.92 Hz, 1H), 3.80 (s, 3H), 3.78 (s, 3H), 3.70 (d, J = 16.92 Hz, 1H), 3.53 (d, J = 15.4 Hz, 1H), 3.03 (d, J = 11.72 Hz, 1H), 2.79-2.86 (dd, J = 13.96, 8.08 Hz, 1H), 2.72 (d, J = 13.92 Hz, 1H), 6.60-6.67 (m, 2H), 7.13-7.63 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.6, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.8, 109.7, 114.2, 114.3, 121.5, 122.3, 122.4, 124.5, 124.6, 124.8, 126.5, 127.4, 128.6, 128.8, 128.5, 128.7, 129.4, 129.9, 130.2, 130.6, 134.6, 136.8, 138.4, 138.4, 138.7, 139.8, 139.7, 144.3, 179.4, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.66; H, 5.32; N, 5.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethoxy)indoline-2,3-dione, its application will become more common.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, belongs to indolines-derivatives 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 3416-57-7, Recommanded Product: 3416-57-7

5.3. Example 3; Cyanoacetamide (62 g, 1.5 eq) and powdered lithium hydroxide (18 g, 1.5 eq) were mixed in 500 ml DMF and it was stirred at room temperature for 30 min. To the mixture was added a solution of phthalimidoacetone (100 g, 0.49 mol, purchased from TCI America, Portland, Oreg., USA, or prepared according to Lei, et al, J. Am. Chem. Soc. 2004, 126, 1626) in DMF (200 ml) over 1 h at room temperature. Additional DMF (25 ml) was used as a rinse. After stirring at room temperature for 5 min, HPLC/MS showed formation of the adol compound (MS: MH+=222.1, MNa+=244.0). Methanol (50 ml) was added followed by 25% sodium methoxide solution (160 g, 1.5 eq) and methanol rinse (50 ml). This mixture was heated at 60-65 C. for 2 h to form 2-amino-4-methyl-1H-pyrrole-3-carboxamide. To this reaction mixture was added ethyl formate (100 ml, 2.5 eq) at 40-60 C. After stirring for 15 min, more methanol (50 ml) was added followed by simultaneous addition of ethyl formate (100 ml, 2.5 eq) and 25% sodium methoxide solution (266 g, 2.5 eq) over 30 min. Additional methanol (50 ml) was added as rinse. The resulting mixture was heated at 60 C. for 5 h. More 25% sodium methoxide solution (113 ml, 1 eq) was added, and heating continued for 1 h more to convert all of the pyrrole N-formyl intermediate (MS: MH+=151.1). Water (400 ml) was added and mixture was heated at 60 C. for 30 min. Solution assay indicated the final product was formed in 69% yield. The hydrolyzed reaction mixture was concentrated under vacuum and diluted with water (1000 ml). The pH was adjusted to about 7.6 with 6 N HCl at 60-65 C. The resulting slurry was heated at 60-65 C. for 15 min and cooled slowly to 10 C. The solids were filtered, washed with water, and dried at 50-60 C. under vacuum. The final product was obtained as a light purple solid (39.5 g, 54% yield, purity: 99.8% by HPLC area).; 5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
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