Category: 645-36-3

Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 163N-(2,2-diethoxyethyl)-5-{4-[4-({[(2-fluoro-5- methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamideA mixture of 5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxylic acid (500mg, 1.12mmol), HATU (467mg, 1.23mmol) and N,N- diisopropylethylamine (322mg, 2.5mmol) in anhydrous DMF (10ml) was stirred at room temperature for 10 minutes, followed by addition of aminoacetaldehyde diethyl acetal (194mg, 1.46mmol). The mixture was stirred for another 10 minutes and poured into 100ml of water. The precipitates were filtered, washed with water and dried in vacuo to give N-(2,2- diethoxyethyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxamide as white solid. Yield: 580mg, 92%. 1H NMR (DMSO-d6): 11.83 (br. s., 1H), 9.18 (s, 1H), 8.49 (d, J = 2.9 Hz, 1H), 8.38 (d, J = 5.6 Hz, 1H), 7.99 (dd, J = 7.9, 2.3 Hz, 1H), 7.94 (t, J = 6.0 Hz, 1H), 7.54 – 7.60 (m, 2H), 7.40 (dd, J = 3.1, 1.6 Hz, 1H), 7.10 – 7.19 (m, 4H), 7.08 (t, J = 2.2 Hz, 1H), 6.78 – 6.84 (m, 1H), 6.71 (dd, J = 5.6, 2.3 Hz, 1H), 4.56 (t, J = 5.6 Hz, 1H), 3.62 (dq, J = 9.7, 7.0 Hz, 2H), 3.47 (dq, J = 9.7, 7.0 Hz, 2H), 3.24 (t, J = 5.7 Hz, 2H), 2.28 (s, 3H), 1.11 (t, J = 7.0 Hz, 6H) LR MS (ES+): 562 (MH+) LR MS (ES-): 560 (M-H)

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; GUO, Xialing; ZHU, Zhen; WO2015/69287; (2015); 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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H15NO2

Compound 19a (1.00 g, 3.34 mmol) was dissolved in DCM (13.4 mL) and diisopropylethylamine (0.87 mL, 5.0 mmol) was added at room temperature followed by addition of aminoacetaldehyde diethylacetal (0.54 mL, 3.67 mmol) and 0-(benzotriazol-l-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (TBTU) (1.13 g, 3.50 mmol). The reaction mixture was stirred for 3 hours at RT, diluted with methylene chloride and washed with 1 M K2C03aqand 1 M HClaq, brine, dried over anhydrous MgS04filtered and concentrated in vacuo. The residue was purified by flash chromatography using dichloromethane (DCM), then DCM/MeOH 100: 1 solvent system. 1.27 g (3.07 mmol; 92% yield) of the title compound 42a was obtainedESI-MS m/z for C20H31CIN2O5 found 415.4/ 417.4(M+1)+ NMR (CDCI3, 500 MHz) delta 7.23 (m, 2H), 7.11 (m, 2H), 5.92 (brs, IH), 5.02 (brs, IH), 4.28 (brs, 2H), 3.64-3.56 (m, 2H), 3.47-3.43 (m, IH), 3.40-3.30 (m, 2H), 3.25 (brs, IH), 2.99 (brs, 2H), 1.38 (s, 9H), 1.14 (q, J = 6.9Hz, 6H)

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONCOARENDI THERAPEUTICS SP. Z O.O.; MAZUR, Marzena; KORALEWSKI, Robert; BOREK, Bartlomiej; OLEJNICZAK, Sylwia; CZESTKOWSKI, Wojciech J.; PIOTROWICZ, Michal C.; OLCZAK, Jacek P.; GOLEBIOWSKI, Adam A.; BARTOSZEWICZ, Agnieszka; MAZIARZ, Elzbieta; KOWALSKI, Michal L.; (274 pag.)WO2017/37670; (2017); A1;,
Ether – 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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,2-Diethoxyethanamine

N- (2,2-Diethoxyethyl)carbodiimide; [0077] A solution of the aminoacetaldehyde diethyl acetal (13.16g, 99 mmol) in ether (35 mL) was added to a suspension ofCNBr (10.47g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Purification by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient) afforded the title compound (7.0 g, 44.7%, one half of the starting amine served as a sacrificial base in the reaction) (Rf; 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid). 1H NMR 400 MHz (CDC13) 8 4.58 (t, J= 5.2 Hz, 1H), 3.77 – 3.69 (m, 2H), 3.65 (br, s, 1H), 3.60 – 3.52 (m, 2H), 3.16 (t, J= 5.6 Hz, 1H), 1.23 (t, 6H, J= 6.8 Hz).

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 645-36-3.

Reference:
Patent; IRM LLC; WO2005/123719; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

Benzaldehyde (1.58 mL, 15.72 mmol) and 2,2-diethoxyethanamine (3.15 g, 23.58 mmol, 1.5 equiv) were stirred at room temperature for 30 minutes. Triacetoxyborohydride (10 g, 47.18 mmol, 3.0 equiv) was diluted slowly in tetrahydrofuran (150 mL, 10 vol) and slowly added dropwise. The reaction mixture was stirred at room temperature for 12 hours. After the reaction was completed, the mixture was diluted with ethyl acetate (200 mL, 15 vol) and washed once with saturated sodium bicarbonate (200 mL, 15 vol) and water (200 mL, 15 vol). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane: ethyl acetate)=1:1 (v/v) to obtain the target compound (3 g, 87%).

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanmi Pharm Co., Ltd.; Bae In-hwan; Park Chang-hui; Ahn Yeong-gil; (28 pag.)KR2019/40763; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 645-36-3, A common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

2,2-Diethoxyethylamine (505 muL, 3.48 mmol) and Et3N (485 muL,3.48 mmol) were added to a soln of pyrimidine 3 (0.5 g, 2.32 mmol)in MeOH (25 mL), and the mixture was stirred at r.t. for 20 h. H2O(100 mL) was added and the precipitate was collected by filtration,dried, and crystallized (hexane) to give a colorless solid; yield: 0.62g (82%); mp 84-85 C.IR (KBr): 3320 (NH), 2220 (CN) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.26 (t, J = 6.9 Hz, 6 H, 2 ¡Á CH3),2.53 (s, 3 H, SCH3), 3.58 (dq, 2J = 9.6 Hz, 3J = 6.9 Hz, 2 H,2 ¡Á CHAHBCH3), 3.69 (t, J = 5.4 Hz, 2 H, NCH2), 3.76 (dq, 2J = 9.6Hz, 3J = 6.9 Hz, 2 H, 2 ¡Á CHAHBCH3), 4.02 (s, 3 H, OCH3), 4.61 (t,J = 5.4 Hz, 1 H, OCH), 5.65 (t, J = 5.4 Hz, 1 H, NH).13C NMR (75 MHz, CDCl3): delta = 14.5, 15.6, 43.8, 54.9, 63.3, 70.6,100.7, 114.7, 162.8, 169.7, 175.6.Anal. Calcd for C13H20N4O3S: C, 49.98; H, 6.45. Found: C, 50.08;H, 6.59.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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Ether | (C2H5)2O – PubChem

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 645-36-3 as follows. Recommanded Product: 2,2-Diethoxyethanamine

[00231] To a solution of cyanogen bromide (25 g, 236.03 mmol) in hexane (80 mL) was added a solution of the amino-acetaldehyde diethyl acetal (34.3 mL, 236.03 mmol) in diethyl ether (80 mL) at room temperature. The resulting mixture was stuffed overnight. A white solid was formed and was removed by filtration and washed with diethyl ether. The filtrate was concentrated and purified by flash chromatography on silica gel (eluted with 0/100 to 5/95 methanol/dichloromethane) to afford N- (2,2-diethyloxyethyl)carbodiimide (27 g, 72% yield) as a bright yellow oil. Rt (retention time) = 1.82 mm; MS m/z: 159.20 [M+1].

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; CHOI, Hwan, Geun; LIANG, Yanke; GRAY, Nathanael; (135 pag.)WO2016/14542; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 645-36-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 645-36-3 name is 2,2-Diethoxyethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 2-bromo-5,6-dihydro-4H-pyrazolo[1,5-d][1,4]diazepine-7(8H)-thione (265.0 mg, 1.07 mmol), 2,2-diethoxyethan-1-amine (1.42 g, 10.7 mmol) and silver carbonate (590 mg, 2.14 mmol) in tetrahydrofuran (10 mL) was stirred at 80 C. for 1 h. The solvent was concentrated under vacuum. The residue was purified by reverse-phase column eluting with water (0.05% TFA)/CH3CN (85/15) to afford 2-bromo-N-(2,2-diethoxyethyl)-5,8-dihydro-4H-pyrazolo[1,5-d][1,4]diazepin-7-amine (295 mg, 80%) as a brown oil. LCMS (ESI) [M+H]+=345.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Diethoxyethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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: 645-36-3

The 2,2-Diethoxy-ethylamine (1852.5 g; 1.00 equiv; 13.63 moles), 3,5-dichloro-benzaldehyde (2453 g; 1.00 equiv; 13.60 moles), and Toluene (12 L) is charged to a 22 L flask equipped with a Dean Stark trap, condenser, nitrogen inlet, overhead stirring, and thermocouple. The light yellow reaction is warmed to reflux. Solvent begins distilling at 88 C. A total of 650 mL distillate (240 mL of water) is collected. The temperature is increased to 114 C. during the distillation. NMR after 2 hr at reflux shows the product. The heat is shut off after 2.5 hr. The solution is gravity filtered into a carboy through fluted filter paper to remove a few particulates (including a small section of glass tubing, which is most likely from the 3,5-dichloro-benzaldehyde). The filtered solution is concentrated using Buchi flask with the water bath set at 45 C. Once the solvent stops coming over, the temperature is increased to 70 C. with full vacuum and held for 1.5 hr to remove any residual toluene. The weight of (3,5-Dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine is 4059.3 g (102.9% of theory). Mass Spectrum (LCMS) m/z=291.2) (M+H+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common.

Reference:
Patent; Joseph, Sajan; Li, Renhua; Myers, Michael Ray; Aburub, Aktham; Dai, Jenny Pingqi; Schmid, Christopher Randall; US2009/221633; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 645-36-3, name is 2,2-Diethoxyethanamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 645-36-3

A suspension of pyrimidine 116 (0.5 g, 2.27 mmol) in MeOH (25mL) was treated by dropwise addition of a soln of 2,2-diethoxyethylamine(395 muL, 23 mmol) in MeOH (5 mL). Na2CO3 (0.29 g,2.73 mmol) was added and the mixture was stirred at r.t. for 1 h.H2O (100 mL) was then added and the resulting precipitate was collectedby filtration, dried, and crystallized (hexane) to give a colorlesssolid; yield: 0.53 g (74%); mp 74-75 C.IR (KBr): 3332 (NH), 2222 (CN) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.28 (t, J = 6.9 Hz, 6 H, 2 ¡Á CH3),2.56 (s, 3 H, SCH3), 3.60 (dq, 2J = 9.6 Hz, 3J = 6.9 Hz, 2 H,2 ¡Á CHAHBCH3), 3.70-3.84 (m, 4 H, NCH2 and 2 ¡Á CHAHBCH3),4.64 (t, J = 5.4 Hz, 1 H, OCH), 5.89 (t, J = 5.4 Hz, 1 H, NH).13C NMR (75 MHz, CDCl3): delta = 14.7, 15.6, 44.0, 63.5, 86.1, 100.2,113.8, 161.2, 161.5, 176.3.Anal. Calcd for C12H17ClN4O2S: C, 45.49; H, 5.41; found: C, 45.62;H, 5.57.

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, 645-36-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem