Analyzing the synthesis route of 134272-64-3

134272-64-3, The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

134272-64-3, N-(2-Aminoethyl)maleimide Hydrochloride is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

GA16OH was used for the synthesis of GA16-MA to increase the solubility in hydrocarbon. To asolution of GA16OH (0.5g, 0.60mmol) in dichloromethane (10 mL) was added N,Ndiisopropylethylamine(0.85ml, 6mmol). The mixture was treated with N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (0.19g, 1mmol), 1-hydroxybenzotriazole (0.13g, 1mmol) and N-(2-aminoethyl)maleimide hydrochloride (0.116g,0.66mmol) and stirred at room temperature overnight. The reaction was quenched with droplet ofHCl (1M) solution and washed with water for three times. The organic portion was dried overNa2SO4. The crude material was purified by silica gel column chromatography using hexane andEtOAc (4/1 to 3/1).1H NMR (400MHz, CDCl3): delta 6.96 (s, 2H), 6.73 (s, 2H), 6.58 (t, J=4.6 Hz, 1H), 4.04-3.96 (m,6H), 3.84-3.82 (m, 2H), 3.66-3.62 (m, 2H), 1.83-1.71 (m, 6H), 1.49-1.45 (m, 6H), 1.37-1.26 (m,72H), 0.90-0.86 (m, 9H)HRMS (ESI): Calculated for C61H108N2O6 ([M+H]+): 965.8286 , found 965.8264.

134272-64-3, The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Qifan; Scigliano, Anita; Biver, Tarita; Pucci, Andrea; Swager, Timothy M.; Bioorganic and Medicinal Chemistry; (2018); p. 5307 – 5313;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Downstream synthetic route of 134272-64-3

134272-64-3, As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

(0432) NHS ester 1a (8.2 mg, 7.6 mumol) (prepared according to procedures described in US 2016/0082114, incorporated herein by reference) and 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (2.2 mg, 0.011 mmol) were dissolved in anhydrous dichloromethane (305 muL) at room temperature. DIPEA (2.66 muL, 0.015 mmol) was added and the reaction and was stirred for 3.5 hours. The reaction mixture was concentrated and was purified by RPHPLC (C18 column, CH3CN/H2O, gradient, 35% to 55%). The desired product fractions were frozen and lyophilized to give maleimide, compound D1 as a solid white powder (5.3 mg, 58% yield). LCMS=5.11 min (8 min method). MS (m/z): 1100.6 (M+1)+.

134272-64-3, As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

Reference£º
Patent; IMMUNOGEN, INC.; Hilderbrand, Scott A.; Hutchins, Benjamin M.; (94 pag.)US2018/208562; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Simple exploration of 134272-64-3

134272-64-3, 134272-64-3 N-(2-Aminoethyl)maleimide Hydrochloride 22118207, apyrrolines compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

To a suspension of the free thiol, 4a (88 mg, 0.105 mmol) and l-((2,5- dioxopyrrolidin-l-yl)oxy)-l-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid (64.0 mg, 0.158 mmol) in anhydrous dichloromethane (2.10 mL) was added DIPEA (55.0 mu, 0.315 mmol) under nitrogen at room temperature. The mixture stirred for 16 hours and then l-(2- aminoethyl)-lH-pyrrole-2,5-dione hydrochloride (55.6 mg, 0.315 mmol), anhydrous dichloromethane (1.0 mL) and DIPEA (0.055 mL, 0.315 mmol) were added. The mixture stirred for an additional 5 hours at room temperature upon which the reaction was concentrated in vacuo. The resulting residue was purified by RP-HPLC (CI 8, CH3CN/H2O). Fractions containing desired product were frozen and lyophilized to give maleimide, compound D4 (20 mg, 16% yield) as a white solid. LCMS = 4.92 min (8 min method). MS (m/z): 1158.6 (M + 1)+.

134272-64-3, 134272-64-3 N-(2-Aminoethyl)maleimide Hydrochloride 22118207, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; IMMUNOGEN, INC.; YODER, Nicholas, C.; BAI, Chen; MILLER, Michael, Louis; (179 pag.)WO2017/4025; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Analyzing the synthesis route of 134272-64-3

134272-64-3, The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

134272-64-3, N-(2-Aminoethyl)maleimide Hydrochloride is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of the free thiol, Dl (88 mg, 0.105 mmol) and l-((2,5- dioxopyrrolidin-l-yl)oxy)-l-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid (sulfo- SPDB) (64.0 mg, 0.158 mmol) in anhydrous dichloromethane (2.10 mL) was added DIPEA (55.0 mu, 0.315 mmol) under nitrogen at room temperature. The mixture stirred for 16 hours and then l-(2-aminoethyl)-lH-pyrrole-2,5-dione hydrochloride (55.6 mg, 0.315 mmol), anhydrous dichloromethane (1.0 mL) and DIPEA (0.055 mL, 0.315 mmol) were added. The mixture stirred for an additional 5 hours at room temperature upon which the reaction was concentrated in vacuo. The resulting residue was purified by RP-HPLC (CI 8, CH3CN/H2O). Fractions containing desired product were frozen and lyophilized to give maleimide, D4 (20 mg, 16% yield) as a white solid. LCMS = 4.92 min (8 min method). MS (m/z): 1158.6 (M + 1)+.

134272-64-3, The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; MACROGENICS, INC.; HICKS, Stuart William; YODER, Nicholas C.; BARAT, Bhaswati; BONVINI, Ezio; DIEDRICH, Gundo; JOHNSON, Leslie S.; LOO, Deryk; SCRIBNER, Juniper A.; (260 pag.)WO2018/119196; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

New learning discoveries about 134272-64-3

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

134272-64-3, N-(2-Aminoethyl)maleimide Hydrochloride is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,134272-64-3

To a solution of NHS ester, 7a (5 mg, 4.82 muetaiotaomicron) and l-(2-aminoethyl)-lH- pyrrole-2,5-dione hydrochloride (1.7 mg, 9.64 muiotaetaomicron) in anhydrous dichloromethane (200 mu) was added DIPEA (1.512 mu, 8.68 muiotaetaomicron) under nitrogen. The mixture was stirred at room temperature for 4 hours and then concentrated in vacuo. The resulting residue was purified by RP-HPLC (CI 8, CH3CN / H20). Fractions containing desired product were frozen and lyophilized to give maleimide, compound D7 (3.5 mg, 68% yield). LCMS = 4.61 min (15 min method). MS (m z): 1062.8 (M + 1)+.

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

Reference£º
Patent; IMMUNOGEN, INC.; MACROGENICS, INC.; HICKS, Stuart William; YODER, Nicholas C.; BARAT, Bhaswati; BONVINI, Ezio; DIEDRICH, Gundo; JOHNSON, Leslie S.; LOO, Deryk; SCRIBNER, Juniper A.; (260 pag.)WO2018/119196; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Downstream synthetic route of 134272-64-3

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of 4-azido-2-hydroxybenzoic acid N-hydroxysuccinimide ester (28 mg, 0.10 mmol) and N-(2-aminoethyl)maleimide hydrochloride (27 mg, 0.15 mmol) in DMF (250 muL) was added (i-Pr)2NEt (53 muL, 0.30 mmol) dropwise at 0 C. The reaction was allowed to warm room temperature, and stirred for 30 min. The reaction mixture was diluted with EtOAc, and then washed with 10% citric acid, H2O and brine. The organic layer was dried over Mg2SO4, and the solution was filtered, concentrated, and flash-chromatographed on silica gel to provide 1 (9.4 mg, 30.8%) as a pale yellow solid: mp >300 C; 1H NMR (CDCl3) delta 3.64 (m, 2H), 3.86 (t, J = 5.2 Hz , 2H) 6.53 (dd, J = 2.3 and 8.6 Hz, 1H) 6.62 (d, J = 2.3 Hz, 1H) 6.77 (s, 2H) 7.36 (d, J = 8.6 Hz, 1H); 13C NMR (CDCl3) delta 37.1, 39.9, 108.1, 110.1, 110.8, 127.2, 134.4, 146.0, 163.1, 169.8, 171.2. MS (ESI), calcd for C13H12N5O4 [M + H]+ 302.1, found 302.1

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

Reference£º
Article; Misu, Ryosuke; Oishi, Shinya; Setsuda, Shohei; Noguchi, Taro; Kaneda, Masato; Ohno, Hiroaki; Evans, Barry; Navenot, Jean-Marc; Peiper, Stephen C.; Fujii, Nobutaka; Bioorganic and Medicinal Chemistry Letters; vol. 23; 9; (2013); p. 2628 – 2631;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Downstream synthetic route of 134272-64-3

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

N-2-ethyl-malimide hydrochloride salt (1.0 g, 5.66 mmol) in THF (50 ml) cooled at -78 C. was added phosphoryl trichloride (0.86 g, 5.66 mmol). After stirred at -78 C. for 2 h to form (2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)phosphoramidic dichloride (2), 3-aminopropanoic acid (0.51 g, 5.70 mmol) in the mixture of THF/H2O (2:1, 30 ml) and triethylamine (1.0 g, 9.90 mmol) was added to the solution. The resulting mixture was stirred at RT for 3 h, concentrated under vacuum and purified on the SiO2 column eluted with H2O/CH3CN (1:201:10) to afford the title compound 4 (1.28 g, 78% yield). ESI MS m/z-C9H13N3O6P (M-H), cacld. 290.06. found 290.10.

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

Reference£º
Patent; SUZHOU M-CONJ BIOTECH CO., LTD; Zhao, Robert Yongxin; US2015/284416; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Brief introduction of 134272-64-3

The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

Trifluoroacetic Acid/4-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]pyrrolidine-3-carboxamide (1:1) 40.5 mg (0.06 mmol) of 4-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (Intermediate C25) and 14.5 mg (0.08 mmol) of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (1:1) were initially charged in 1.0 ml of acetonitrile, and 64.4 mg (0.51 mmol) of N,N-diisopropylethylamine and 50.0 mg (0.08 mmol) of T3P were added and the mixture was stirred at RT for 16 h. The same amount of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (1:1), N,N-diisopropylethylamine and T3P were added again, and the mixture was stirred at RT for a further 4 h. The reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 125*30; 10mu, flow rate: 50 ml/min, MeCN/water). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 7.2 mg (15% of theory) of the compound tert-butyl 3-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-4-{[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamoyl}pyrrolidine-1-carboxylate. LC-MS (Method 1): Rt=1.30 min; MS (ESIpos): m/z=763 [M+H]+.

The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Pharma Aktiengesellschaft; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; MARX, Leo; STELTE-LUDWIG, Beatrix; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (684 pag.)US2018/169256; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Brief introduction of 134272-64-3

The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

Step 2: To a solution of the NHS ester, compound 6a (12.3 mg, 0.011 mmol) and N-(2- aminoethyl)maleimide hydrochloride (2.0 mg, 0.011 mmol) in anhydrous dichloromethane (0.3 niL) was added DIPEA (0.0022 niL, 0.013 mmol). The mixture was stirred at room temperature for 3 hours then it was stripped under reduced pressure. The residue was purified by semi-preparative reverse phase HPLC (CI 8 column, CH3CN/H2O). The fractions that contained pure product were combined, frozen and lyophilized to give the desired maleimide, compound D6 (10 mg, 80% yield). LCMS = 8.3 min (15 min method). MS (m/z): 1181.8 (M + 1)+.

The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; KOVTUN, Yelena; TAVARES, Daniel; RUI, Lingyun; CHITTENDEN, Thomas; (386 pag.)WO2017/4026; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Simple exploration of 134272-64-3

134272-64-3 N-(2-Aminoethyl)maleimide Hydrochloride 22118207, apyrrolines compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

NHS ester 5a (8.2 mg, 7.6 muiotaetaomicron) and l-(2-aminoethyl)- lH-pyrrole-2,5-dione hydrochloride (2.2 mg, 0.011 mmol) were dissolved in anhydrous dichloromethane (305 ) at room temperature. DIPEA (2.66 mu, 0.015mmol) was added and the reaction and was stirred for 3.5 hours. The reaction mixture was concentrated and was purified by RPHPLC (CI 8 column, CH3CN/H2O, gradient, 35% to 55%). The desired product fractions were frozen and lyophilized to give maleimide, compound D5 as a solid white powder (5.3 mg, 58% yield). LCMS = 5.11 min (8 min method). MS (m/z): 1100.6 (M + 1)+.

134272-64-3 N-(2-Aminoethyl)maleimide Hydrochloride 22118207, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; IMMUNOGEN, INC.; YODER, Nicholas, C.; BAI, Chen; MILLER, Michael, Louis; (179 pag.)WO2017/4025; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem