Category: 869494-16-6

Related Products of 869494-16-6,Some common heterocyclic compound, 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, molecular formula is C10H18N2O2, 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.

Under inert atmosphere (N2(g)), a mechanically stirred suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (49.3 g, 249 mmol) in DMSO (200 mL) was treated with 4-(6-fluoropyridin-3 -yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5- a]pyridine-3-carbonitrile (Intermediate P42; 58 g, 178 mmol), and DIEA (93.1 mL, 533 mmol) was stirred 42 h at 90 C. After cooling to ambient temperature, the reaction mixture was poured into ice water (2 L). The aqueous mixture was stirred for 15 mm before Heptane (1 L) was added. The biphasic mixture was stirred vigorously for 2 h. The resulting biphasic suspension was vacuum filtered and the solids were rinsed sequentially with water (3 x 200 mL) and heptane (3 x 200 mL) to afford a product mixture containing 5-20% of the title compound, tert-butyl 6-(5-(3- cyano-6-(2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridin-4-yl)pyridin-2-yl)-3 , 6- diazabicyclo[3. 1.1 ]heptane-3 -carboxylate, along with the regioi somer, tert-butyl 3 -(5 -(3 -cyano-6- (2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridin-4-yl)pyridin-2-yl)-3 ,6- diazabicyclo[3. 1.1 ]heptane-6-carboxylate (Intermediate P43, step 1) (92 g, quantitative yield). The regioisomeric mixture was carried into Step 2 without separating (note: 3,6-diaza- bicyclo[3.1. 1 ]heptane-6-carboxylic acid tert-butyl ester can partially isomerize to the regioisomer, 3, 6-diaza-bicyclo[3. 1.1 ]heptane-3 -carboxylic acid tert-butyl ester, under these reaction conditions.) MS (apci) m/z = 505.3 (M+H).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (266 mg, 1.34 mmol), 2,5- dichloropyrazine (260 mg, 1.74 mmol) and K2C03(s) (927 mg, 6.71 mmol) in DMSO (1.5 mL)was stirred for 2 h at 80 °C, then overnight at 85 °C. After cooling to ambient temperature, the mixture was diluted with water and stirred vigorously until the ensuing exotherm dissipated. The aqueous mixture was extracted with Et20, and the biphasic mixture was filtered and separated. The aqueous phase was extracted with DCM, and the Et20 and DCM extracts were combined. The combined organic extracts were dried over anhydrous MgSO4(), filtered, and concentrated in vacuo. The residue was purified by silica chromatography (10percent EtOAc in DCM with 0.05percent NH4OH as the eluent) to cleanly provide the title compound (286 mg, 69percent yield). MS (apci) m/z = 311.0 (M+1); 313.2 (M+2) with Cl pattern.

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 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H18N2O2

A mixture of (R)-4-(6-fluoropyridin-3 -yl)-6-(2-hydroxypropoxy)pyrazolo[ 1,5 – a]pyridine-3-carbonitrile (Intermediate P66; 100 mg, 0.320 mmol) 3,6-diaza- bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (95.2 mg, 0.480 mmol) and K2C03(s) (443 mg, 3.20 mmol) in DMSO (1601 tL) was stirred for 3 d at 80 °C. The reaction mixture was cooled to ambient temperature, then diluted with water (10 mL), and extracted with DCM (4 x 10 mL). The combined organic extracts were washed with brine (10 mL), then dried over anhydrous Na2SO4(), filtered, and concentrated in vacuo. The crude residue was purified by silica chromatography (using 50-100percent EtOAc in Hexanes as the gradient eluent) to cleanly provide the title compound (97 mg, 62percent yield). MS (apci) m/z = 491.2 (M+H).

According to the analysis of related databases, 869494-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 869494-16-6, These common heterocyclic compound, 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-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.

In a microwave vial a solution of 3 -chloro-4-(6-fluoropyridin-3 -yl)-6-( i-methyl-i Hpyrazol-4-yl)pyrazolo[i,5-a]pyridine (Intermediate P9; 5 mg, 0.015 mmol) and tert-butyl 3,6- diazabicyclo[3.i.i]heptane-6-carboxylate (9.1 mg, 0.046 mmol) in DMSO (0.2 mL) was subjected to microwave irradiation at 130 °C for 5 h and then at 150 °C for 6 h. The reaction mixture was cooled to ambient temperature and then directly purified by reverse phase chromatography (5-95percent ACN/water) to afford the title compound (2.6 mg, 34percent yield). ?H NIVIR (CDC13) 8.51 (d, 1H), 8.34 (d, 1H), 7.88 (s, 1H), 7.76 (s, 1H), 7.65 (m, 2H), 7.12 (d, 1H), 6.62(d, 1H), 4.33 (m, 2H), 4.20 (m, 2H), 3.98 (s, 3H), 3.55 (m, 2H), 1.45 (d, 2H), 1.38 (s, 9H).

Statistics shows that tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate is playing an increasingly important role. we look forward to future research findings about 869494-16-6.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C10H18N2O2

A mixture of 6-ethoxy-4-(6- fluoropyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile (Intermediate P6; 347 mg, 1.23 mmol), tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (365.6 mg, 1.844 mmol) and K2C03(s) (1.699 g, 12.29 mmol) in DMSO (6.15 mL) was stirred for 3 days at 80°C. The reaction mixture was cooled to ambient temperature, then diluted with water and extracted with DCM. The combined organic extracts were washed with brine, then dried over anhydrous Na2SO4(), filtered and concentrated in vacuo. The crude residue was purified by silica chromatography (50-100percent EtOAc in Hexanes as the gradient eluent) to cleanly provide the title compound (434.5 mg, 77percent yield). MS (apci) m/z = 461.2 (M+H).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H18N2O2

To a solution of 4,5-dibromo-2,3-dihydropyridazin-3-one (461.0 mg, 1.82 mmol, 1.2 equiv.) in DMA(10 mL, 107.55 mmol) were added tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6- carboxylate(300 mg, 1.51 mmol, 1 equiv.) and DIEA(391.1 mg, 3.03 mmol, 2 equiv.) at ambient temperature. The resulted mixture was stirred for 16 h at 100 degrees C. The reaction mixture was diluted with water(200 mL) and extracted with ethyl acetate(3*200 mL).The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions(Column: spherical C18, 20-40 um,330g; Mobile Phase A: Water(5mmol/L NH4HCO3), Mobile Phase B: MeCN; Flow rate: 80 mL/min; Gradient: 10% B to 60% B in 55 min; 254 nm) to afford tert-butyl 3-(5-bromo-6-oxo-1,6- dihydropyridazin-4-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate(230mg,40.95%) as a light yellow solid.

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; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 869494-16-6,Some common heterocyclic compound, 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, molecular formula is C10H18N2O2, 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.

Under inert atmosphere (N2(g)), a mechanically stirred suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (49.3 g, 249 mmol) in DMSO (200 mL) was treated with 4-(6-fluoropyridin-3 -yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5- a]pyridine-3-carbonitrile (Intermediate P42; 58 g, 178 mmol), and DIEA (93.1 mL, 533 mmol) was stirred 42 h at 90 C. After cooling to ambient temperature, the reaction mixture was poured into ice water (2 L). The aqueous mixture was stirred for 15 mm before Heptane (1 L) was added. The biphasic mixture was stirred vigorously for 2 h. The resulting biphasic suspension was vacuum filtered and the solids were rinsed sequentially with water (3 x 200 mL) and heptane (3 x 200 mL) to afford a product mixture containing 5-20% of the title compound, tert-butyl 6-(5-(3- cyano-6-(2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridin-4-yl)pyridin-2-yl)-3 , 6- diazabicyclo[3. 1.1 ]heptane-3 -carboxylate, along with the regioi somer, tert-butyl 3 -(5 -(3 -cyano-6- (2-hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridin-4-yl)pyridin-2-yl)-3 ,6- diazabicyclo[3. 1.1 ]heptane-6-carboxylate (Intermediate P43, step 1) (92 g, quantitative yield). The regioisomeric mixture was carried into Step 2 without separating (note: 3,6-diaza- bicyclo[3.1. 1 ]heptane-6-carboxylic acid tert-butyl ester can partially isomerize to the regioisomer, 3, 6-diaza-bicyclo[3. 1.1 ]heptane-3 -carboxylic acid tert-butyl ester, under these reaction conditions.) MS (apci) m/z = 505.3 (M+H).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate

A mixture of 1-bromo-4-iodobenzene (0.500 g, 1.77 mmol), tert-butyl 3,6- diazabicyclo[3.1.1]heptane-6-carboxylate (0.491 g, 2.47 mmol), C52CO3(s) (1.15 g, 3.53 mmol), CuT (16.8 mg, 0.0884 mmol) and 2-isobutyrylcyclohexan-1-one (59.5 mg, 0.353 mmol) in DMF (1.5 mL) was sparged with Ar(g) for 5 mm, then stirred for 4 days at ambient temperature. The reaction mixture was treated with additional CuT (16.8 mg, 0.0884 mmol), then sparged with Ar(g) for 5 mm and stirred at 35 ¡ãC for 1 h. The mixture was partitioned between brine and MTBE. The organic layer was separated and washed with additional brine and saturated NH4C1(aq). The aqueous extracts were combined and back extracted with MTBE. The MTBE extracts were combined, then dried over anhydrous MgSO4(), filtered, and concentrated in vacuo. The crude residue was purified by silica chromatography (DCM as the eluent) to cleanly provide the title compound (190 mg, 30percent yield). MS (apci) m/z = 353.0 (M+1); 355.1 (M+2) with Br pattern.

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(5-Amino-1-[4-(2-fluorophenoxy)-2-methylphenyl]pyrazol-4-yl}-[6-bromo-5-(2-bromoethoxy)-1H-indol-2-yl]methanone (100 mg) was suspended in acetonitrile (1.0 mL), tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (63 mg) and cesium carbonate (130 mg) were added, and the mixture was stirred at 70¡ãC for three hours. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate. After removing the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane/ethyl acetate) to give the target compound (79 mg).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; F. Hoffmann-La Roche AG; EBIIKE, Hirosato; AOKI, Toshihiro; CHIBA, Takashi; KOCHI, Masami; NAKAMA, Kimitaka; NIIZUMA, Satoshi; NISHII, Hiroki; OHWADA, Jun; SHIMAMURA, Hiroyuki; SUGE, Aiko; NAKANISHI, Yoshito; KOBAYASHI, Natsuki; (594 pag.)EP3312172; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below.

A suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (182 mg, 0.918 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (819 mg, 3.67 mmol) and K2C03(S) (634 mg, 4.59 mmol) in DMSO (918 was heated to 90 ¡ãC, then treated with water (5 mL). The resulting mixture was stirred for 1 hour at 90 ¡ãC, then cooled to ambient temperature and filtered to cleanly provide the title compound (1.0 g, 41percent yield). MS (apci) m/z = 320.1 (M+H).

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; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics