Category: 264916-06-5

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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 264916-06-5

Step-1: Synthesis of tert-butyl 5-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-(methylthio)-1,2-dihydro-3H-indazol-3-one (200 mg, 0.582 mmol, 1.0 eq) in (2.0 mL) of toluene was added m-CPBA (287 mg, 1.164 mmol, 2.0 eq) and allowed to stir at rt for 30 minutes. tert-butyl 5-aminoisoindoline-2-carboxylate (164 mg, 0.698 mmol, 1.2 eq) and DIPEA (0.40 mL, 2.328 mmol, 4.0 eq) were added and allowed to stir at rt for overnight. The formation of precipitates were observed which were filtered to afford the desired compound tert-butyl 5-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (135 mg, 43.83%) as brown solid.

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 264916-06-5.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 264916-06-5,Some common heterocyclic compound, 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, molecular formula is C13H18N2O2, 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.

Step-1: Synthesis of tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-indazol-3-one (120 mg, 0.34 mmol, 1.0 eq) in (2.0 mL) of toluene was added m-CPBA (91 mg, 0.37, 1.1 eq) and allowed to stir at rt for 30 minutes. tert-butyl 5-aminoisoindoline-2-carboxylate (102 mg, 408 mmol, 1.2 eq) and DIPEA (0.30 mL, 1.7 mmol, 5.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography to afford the desired product, tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (40 mg, 21.73%) as brown solid.

The synthetic route of 264916-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 264916-06-5, 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 264916-06-5 as follows.

2-Boc-5-Aminoisoidoline (50 mg, 0.21 mmol) was added to a solution of NaOMe in MeOH (4 mL of0.26 M, 1.05 nimol) . This solution was then combined with a solution of paraformaldehyde (9.5 mg, 0.32 rnmol) in MeOH (2 mL) . The solution was stirred overnight (about 18 hours) at room temperature, after which time NaBH4 (8 mg, 0.21 mmol) was added and the reaction mixture was heated at reflux for 5 hours. After cooling to room temperature, the reaction was quenched with the addition of saturated aq. NH4C1 (1 mL), then diluted with water (about 20 mL) and extracted with CH2C12. The organic extracts were dried over Na2SO4. After removal of the solvent, the product was purified by flash chromatography (Si02, 15-45% EtOAc/hexanes gradient). Yield: 25.6mg (52%), pale yellow oil, Mixture of rotamers. ?H NMR (400 MHz, CDC13) 5 7.04 and 6.09 (d, J = 8.3 Hz, 1H) , 6.73 – 6.45 (m, 2H) , 4.72 – 4.47 (m, 4H) , 3.52 (s, 1H) , 1.50 (s, 9H) . ?3C NMR (151 MHz, CDC13) 5 148.0, 138.5, 123,6, 123.3, 113.6, 113.5, 107,1, 107.0, 79.7, 52.6,52.3, 52.0, 51.6, 31.9, 31.8, 28.71, 28.67. FIRESITOE m/z 249.1597 (014H20N202 + H, required 249.1597)

According to the analysis of related databases, 264916-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (R)-1-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-yl) amino)piperidin- 1-yl)prop-2-en-1-one (64.2) (100 mg, 0.3 mmol), tert-butyl 5-aminoisoindoline-2-carboxylate (1.5) (64 mg, 0.27 mmol), Cs2CO3 (177 mg, 0.54 mmol), tris(dibenzylideneacetone)dipalladium(0) (25 mg, 0.03 mmol), and Davephos (10 mg, 0.03 mmol) in tert-amyl alcohol (10 mL) was stirred at 100 C for 3 h. The mixture was quenched with the addition of water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to dryness to afford the crude product. The crude product was purified by column chromatography (hexanes/ethyl acetate: 1/1) to afford (R)-1-(3-((2-(isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4- yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65).The product was taken up in DCM/TFA (5 mL/3 mL) and stirred at room temperature for 30 min. The mixture was concentrated to dryness to afford the TFA salt of (R)-1-(3-((2- (isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65) as a white solid (35 mg, 21%). [00915] LCMS: 433.1 [M+1]+. [00916] 1HNMR (400 MHz, CD3OD): delta 1.58-1.61 (m, 1H), 1.86-1.91 (m, 2H), 2.03-2.09 (m, 1H), 2.88-2.96 (m, 0.5H), 3.04-3.10 (m, 0.5H), 3.15-3.22 (m, 0.5H), 3.26-3.27 (m, 0.5H), 3.98- 4.10 (m, 1H), 4.29-4.39 (m, 1.5H), 4.49-4.63 (m, 4.5H), 5.47 (d, 0.5H), 5.84 (d, 0.5H), 6.05 (d, 0.5H), 6.28 (d, 0.5H), 6.40 (dd, 0.5H), 6.86 (dd, 0.5H), 7.36-7.39 (m, 1H), 7.58 (dd, 1H), 7.81 (s, 1H), 8.24 (d, 1H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5-aminoisoindoline-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C13H18N2O2

(2) 2-tert-Butoxycarbonyl-5-(2-nitrophenylamino)isoindoline A dimethylformamide (10 ml) suspension of 5-amino-2-tert-butoxycarbonylisoindoline (5.3 g, 22.6 mmol), o-fluoronitrobenzene (7.15 ml, 22.6 mmol) and potassium carbonate (3.12 g, 22.6 mmol) was stirred at 145 C. for 2 hours under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water. After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography to give 2-tert-butoxycarbonyl-5-(2-nitrophenylamino)isoindoline (4.9 g, 61%) as an oil. 1H-NMR(CDCl3) delta: 1.53(9H, s), 4.67(2H, s), 4.70(2H, s), 6.76(1H, t, J=6.8 Hz), 7.15-7.41(5H, m), 8.20(1H, d, J=8.8 Hz), 9.47(1H, bs).

The synthetic route of 264916-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Oi, Satoru; Suzuki, Nobuhiro; Matsumoto, Takahiro; US2003/149027; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cooled solution of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (13 mL, 26 mmol) at 5C was added dropwise a solution of 5-amino-l,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in tetrahydrofuran (50 mL). Gas evolution was noted. The mixture was stirred for 1 hour at 5C then warmed to room temperature and stirred for 24 hours. The mixture was cooled to 5C in a ice/water bath and the reaction was quenched by addition of sodium sulfate decahydrate (3 g). Gas evolution noted. The mixture was stirred for 2 hours at room temperature. The suspension was filtered through a plug of diatomaceous earth and rinsed with with tetrahydrofuran. The filtrate was dried over magnesium sulfate, filtered and evaporated. The residue was purified via flash chromatography (silica gel column and 0%?20% methanol: dichloromethane). 2-Methyl-2,3-dihydro-lH-isoindol-5-ylamine was isolated as an orange solid (0.271 g, 43%). 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 6.82 (d, J=I .9 Hz, IH), 6.41 (s, IH), 6.37 (d, J=8.1 Hz, IH), 4.86 (br s, 2H), 3.64 (s, 2H), 3.62 (s, 2H), 2.42 (s, 3H). MS = 149 (MH)+.

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; CURRY, Matthew A.; DORSEY, Bruce D.; DUGAN, Benjamin J.; GINGRICH, Diane E.; MESAROS, Eugen F.; MILKIEWICZ, Karen L.; WO2010/141796; (2010); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 264916-06-5, name is tert-Butyl 5-aminoisoindoline-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. Product Details of 264916-06-5

To 517 mg of P14 in 15 ml_ of THF at O0C was added 350 mg of 60% sodium hydride in mineral oil and the mixture stirred for 10 minutes. 570 mg of P15 was then added and the mixture warmed to room temperature. After three days the reaction mixture was quenched with water then extracted three times with ethyl acetate. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and evaporated to dryness. Purification by flash chromatography yielded 450mg of 8. LCMS: 433.2 (MH+)

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Synthetic Route of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 2-Boc-5-aminoisoindoline (20mg, 0.085 minol) and a carboxylic acid (0.102 rnmol) in DMF (1 mL) was treated with 1-[bis (dimethylamino)methylene] -1H-1, 2, 3-tr¡Àazolo[4, 5- b]pyridinium 3-oxid hexafluorophosphate (HATU; 39 mg, 0.102 mmol) and i-Pr2NEt (17 pL, 0.102 mmol) . The reaction was allowed to proceed overnight (about 18 hours), after which the solution was diluted with EtOAc (about20 mL) . The diluted reaction was extracted twice with saturated aq. NaHCO3 and once with saturated aq. NaC1. The organic layer was dried over Na2SO4. The products were purified by flash chromatography (SiC2) using an EtOAc/hexanes solvent gradient. Yield: 20.1 mg (78%), white solid, mixtureof rotamers. ?H NMR (600 MHz, ODd3) 7.75 – 7.55 (m,1H), 7.51 (s, 1H), 7.42 – 7.22 (m, 1H), 7.17 and 7.14(d, J = 8.2 Hz, 1H) , 7.05 – 6.92 (m, 1H) , 5.97 and5.95 (d, J = 1.7 Hz, 1H), 4.79 – 4.40 (m, 4H), 1.90(dd, J = 6.9, 1.7 Hz, 3H), 1.51 (s, 9H) . NMR (151MHz, ODd3) 164.2, 154.7, 141.8, 137.7, 125.5,123.2, 123.0, 119.4, 114.5, 79.9, 52.5, 52.2, 52.1,51.8, 28.7, 18.0. HRESI-TOF m/z 303.1702 (C,7H22N203 +H, required 303.1703)

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 5-aminoisoindoline-2-carboxylate

tert-Butyl 5-aminoisoindoline-2-carboxylate (200 mg, 0.854 mmol),3,4-dimethoxyphenylboronic acid (155 mg, 0.854 mmol) and monohydrate glycolic acid (63 mg, 0.854 mmol) were dissolved in acetonitrile/DMF (2 mL each). The reaction was heated at 110 0C for 10 min. in a microwave. The reaction was concentrated to an oil and purified with preparatory HPLC to yield 12A (309 mg, 0.721 mmol) in 84% yield. 1H NMR (400 MHz, CDCl3) delta ppm 1.45 – 1.51 (m, 9 H) 3.84 – 3.88 (m, 6 H) 4.48 – 4.56 (m, 4 H) 4.99 (d, J=6.59 Hz, 1 H) 6.36 – 6.55 (m, 2 H). MS (ESI) m/z 429.4 (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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step-1: tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (0.2 g 0.5790 mmol, 1.0 eq) in (5.0 mL) of toluene was added m-CPBA (0.280 g, 1.158 mmol, 2 eq) and allowed to stir at rt for 30 min. followed by addition of tert-butyl 5-aminoisoindoline-2-carboxylate (0.176 g, 0.7527 mmol, 1.3 eq) and DIPEA (0.3 ml 1.737 mmol, 3.0 eq) and allowed to stir at rt for overnight. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic layers were washed with water (30 mL), brine (30 mL), dried over Na2SO4, concentrated and purified by combi flash [silica gel-100-200 mesh; elution 0-35% EtOAc in Hexane] to afford the desired compound, tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (0.100 g, 49.52%) as white solid.

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 5-aminoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem