Category: 6228-73-5

Application of 6228-73-5,Some common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, molecular formula is C4H7NO, 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 3 To a reaction vial was added the product from Step 2 (20 mg, 0.056 mmol), cyclopropanecarboxamide (4.74 mg, 0.056 mmol) and BrettPhos (3.59 mg, 6.69 muiotaetaomicron) and the contents were purged with nitrogen before adding DMA (0.10 mL) and dioxane (0.20 mL). The resulting slurry was sparged with nitrogen for an additional minute, then Pd2(dba)3 (5.10 mg, 5.57 muiotaetaomicron) followed by LiHMDS (1 M in THF) (0.139 mL, 0.139 mmol) was added and the reaction vial was capped under nitrogen and placed into a preheated 110 C heating block and the mixture was allowed to stir at that temperature for 1.5h. After cooling, the reaction was quenched with MeOH, concentrated to remove the volatiles, and was purified by reverse phase preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 0-100% B over 20 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product (Example 29) was 15.4 mg (49%). HPLC (Method E) RT = 0.98 min. HPLC (Method G) RT = 0.76 min. LCMS observed MH+ = 408.2. 1H NMR (500MHz, DMSO-d6) delta 11.11 (br. s., 1H), 10.82 (br. s., 1H), 8.79 (br. s., 1H), 8.49 (s, 1H), 7.75 (d, J=6.7 Hz, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.38 – 7.27 (m, 1H), 3.69 (s, 3H), 2.81 (d, J=4.3 Hz, 3H), 1.91 (br. s., 1H), 0.90 – 0.78 (m, 4H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a microwave tube was added7-chloro-2-(2,6-dichlorophenyl)thieno[2,3-c]pyridine(150 mg, 0.48 mmol),cyclopropanecarboxamide(81 mg, 0.95 mmol), Pd2(dba)3(22 mg, 0.024 mmol), XantPhos (28 mg, 0.048 mmol), Cs2CO3(311 mg, 0.95 mmol) and dioxane (4 mL).The mixture was degassed with N2for 10 min. The resulting mixture was irradiated in a microwave reactor at 150 C for 1.5 h and then cooled to room temperature. The mixture was filtered throughCeliteand the filtrate was concentrated. The residue was purified by silica gel column chromatography eluting with a 0-60% gradient ofEtOAcin dichloromethane to afford a solid. The solid was triturated with diethyl ether and collected by filtration to afford the title compound (110 mg, 64% yield). H NMR (300 MHz, CDCl3):delta 8.96 (1H,brs), 8.21 – 8.17 (1H, m), 7.55 (1H, d,J= 5.5 Hz), 7.45 – 7.41 (2H, m), 7.35-7.24 (2H, m), 1.24 – 1.15 (3H, m), 0.99 – 0.91 (2H, m); LCMS (ESI) m/z: 363.2 [M+H]+.HRMS m/z [M+H]+calcd.forC17H12Cl2N2OS 363.0125, found 363.0118.

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

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows.

Cyclopropanecarboxamide (58.7g, 690 mmol) in 1,4-Dioxane (1600 ml) was added 2-bromoacetyl bromide (59.9 ml, 690 mmol) at room temperature and stirred for 4h at 600C. The reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and carefully washed with satd. NaHCObeta, water then with brine solution, dried over Na2SO4 and concentrated to get N-(2- bromoacetyl) cyclopropanecarboxamide(138 g, 670 mmol, 97 % yield) as an off white solid. This material was used without purification. ESI-MS :m/z 208.0 (M+2H)+.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, 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. SDS of cas: 6228-73-5

Step 1 : 4-(Chloromethyl)-2-cyclopropylthiazole[0174] To a slurry of cyclopropanecarboxamide (10 g, 0.12 mol) in MTBE (150 rnL) was charged P2S5 (5 g, 12 mmol). The mixture was heated to 100 0C for 2 h (monitored by TLC, EtOAc/hexane 1 :1) and cooled to room temperature. Supernatant was decanted and concentrated to afford the intermediate thioamide (6 g, 56%) as a light yellow solid. MS (ES) m/z 102.1 (M+ H+)). This was suspended in acetone (100 mL) and charged with 1,3- dichloroacetone (7.0 g, 0.055 mol). The mixture was heated to reflux for 8 h (monitored by TLC, EtOAc/hexane 1 :1), cooled to room temperature and concentrated. The residue was purified by silica gel chromatography using 2 to 10% EtOAc in hexane to afford the title compound (8.0 g, 79%) as a light brown oil. 1H NMR (400 MHz, CDCl3) delta 7.02 (s, IH), 4.62 (s, 2H), 2.32 (m, IH), 1.16 (m, 2H), 1.05 (m, 2H). MS (ES) m/z 174.1 (M+ H+).

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

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pinchen; GLEASON, Mark, M.; JAEN, Juan, C.; LI, Lianfa; MCMAHON, Jeffrey, P.; POWERS, Jay; ZENG, Yibin; ZHANG, Penglie; WO2010/54006; (2010); 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. 6228-73-5, name is Cyclopropanecarboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H7NO

General procedure: Synthesis of 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4) Procedure A: A mixture of 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine (3, 0.10 g, 0.37 mmol), 5-bromo-2-methylisoindolin-1-one (2, 0.10 g, 0.45 mmol), sodium tert-butoxide (54 mg, 0.56 mmol) and XPhos (5 mg, 0.01 mmol) in toluene (10 mL) was degassed with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol) was added under argon atmosphere and the reaction mixture was heated at 100 C. for 12 h. After completion of the reaction, the reaction mixture was filtered through celite pad and the filtrate was concentrated. The crude residue was purified by silica gel column chromatography using 0-10% ethyl acetate in hexanes as eluent to afford 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4). Yield: 0.11 g, 71%; MS (ESI) m/z 411 [M+1]+.

The synthetic route of 6228-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Mix the compound obtained in Step 2 (610 mg, 1.9 mmol), cyclopropanecarboxamide (193 mg, 2.27 mmol), (±)-2,2-bis(diphenylphosphino)-l,l’-binaphthalene (BINAP, 118 mg, 0.19 mmol), CS2CO3 (1.238 g, 3.8 mmol) and tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 122 mg, 0.133 mmol] in 1,4-dioxane (30 mL). Stir the reaction at 120C under N2 for 16 hrs. Cool the reaction, filter, concentrate the filtrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=l:l) affords the title compound (500 mg, 70.8%). MS: (M+l): 372.2.

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

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows.

Cyclopropanecarboxamide (58.7g, 690 mmol) in 1,4-Dioxane (1600 ml) was added 2-bromoacetyl bromide (59.9 ml, 690 mmol) at room temperature and stirred for 4h at 600C. The reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and carefully washed with satd. NaHCObeta, water then with brine solution, dried over Na2SO4 and concentrated to get N-(2- bromoacetyl) cyclopropanecarboxamide(138 g, 670 mmol, 97 % yield) as an off white solid. This material was used without purification. ESI-MS :m/z 208.0 (M+2H)+.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); 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 6228-73-5 as follows. Quality Control of Cyclopropanecarboxamide

Cyclopropanecarboxamide (22.5 mg, 0.26 mmol) was combined with Int3 (30 mg, 0.088 mmol). Dimethylacetamide (DMA, 0.6 mL) was added to the vessel, followed by the addition of tris (diphenylmethyleneacetone) dicum (0) (Pd2dba3, 8.1 mg, 0.0088 mmol)4,5-bis (diphenylphosphino) -9,9-dimethyl(Xantphos, 10 mg, 0.018 mmol) and cesium carbonate (115 mg, 0.35 mmol). The vessel was then evacuated and backfilled three times with nitrogen and heated to 145 & lt; 0 & gt; C for 1 hour.The reaction was cooled to room temperature and then diluted with ethyl acetate (EtOAc, ca. 250 mL). The solution was washed twice with water, dried over sodium sulfate (Na2SO4), filtered, concentrated and purified using preparative HPLC. The product in the form of TFA salt was collected and then dissolved in about 15 mL of water, to which about 100 mL of saturated sodium bicarbonate (NaHCO3, an aqueous solution) was added and stirred for 10 minutes. The product of (x3) was extracted from the slurry using dichloromethane (DCM), dried over sodium sulfate, filtered, concentrated and collected to give 16.3 mg of 1 (48% yield).

According to the analysis of related databases, 6228-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN,, RYAN M.; WEINSTEIN,, DAVID S.; WROBLESKI,, STEPHEN T.; ZHANG,, YANLEI; TOKARSKI,, JOHN S.; MERTZMAN,, MICHAEL E.; LIU,, CHUNJIAN; (124 pag.)TWI582077; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows.

Example A7 A suspension of Example A1 (2.00 g, 7.95 mmol), Cs2CO3 (5.00 g, 15.35 mmol), XPhos (0.200 g, 0.420 mmol), Pd2(dba)3 (0.200 g, 0.218 mmol) and cyclopropylcarboxamide (1.00 g, 11.75 mmol) in dioxane (20 mL) was heated at 90 C. under argon overnight. The mixture was cooled to RT and the solids removed via filtration and washed with DCM and THF. The filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.52 g, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.01 (s, 1H), 8.57 (dd, J=2.8, 0.5 Hz, 1H), 8.40 (m, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.98 (dd, J=8.9, 2.8 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 1.97 (m, 1H), 0.77 (m, 4H); MS (ESI) m/z: 301.1 (M+H+).

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

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); 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. 6228-73-5, name is Cyclopropanecarboxamide, A new synthetic method of this compound is introduced below., Computed Properties of C4H7NO

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4- c]pyridine (60 mg, 0.17 mmol), cyclopropanecarboxamide (0.019 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2C03 (0.11 g, 0.34 mmol) in dioxane (3 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160 C for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified by reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HC03 to give the desired product as a white solid (13 mg, 21% yield). l NMR (500 MHz, DMSO- 6): delta 11.44 (s, 1H), 8.46 (d, J= 6.0 Hz, 1H), 7.92 (d, J= 6.0 Hz, 1H), 7.72-7.67(m, 3H), 2.09-2.06 (m, 1H), 0.9-0.87 (m, 4H). LCMS (Method A): RT = 5.84 min, m/z: 371.0 [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; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics