Category: 262368-30-9

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10.5 [G] (30.0 [MMOL)] of [1-ACETYL-3- (1-ETHOXY-1-PHENYLMETHYLENE)-6-METHOXYCARBONYL-2-] indolinone (for preparation see WO 01/27081 mentioned above) and 8.60 g (33.0 [MMOL)] [N- [ (4-METHYL-PIPERAZIN-1-YL)-METHYLCARBONYL]-N-METHYL-P-PHENYLENEDIAMINE] (for preparation see WO 01/27081 mentioned above) are dissolved in 80 mL of dimethylformamide and stirred for 1 hour at [80C.] After cooling 6.50 mL of piperidine are added and the mixture is stirred for another two hours at ambient temperature. Water is added, the precipitate formed is suction filtered and washed with a little water. The residue is suspended in 200 mL of methanol, suction filtered and washed with cold water and diethyl ether. The substance is [DRIED IN VACUO] at 110 [C.] Yield : 12.4 g (77% of theory), [IR SPECTRUM] : 1610,1655, 1711 cm-1 Tm. p. = [253C] [EMPIRICAL FORMULA : C31H33N504] [ESI] mass spectrum: m/z = 540 [M+H]+ Elemental analysis: calculated: C 68.99 [H-6.] 16 [N 12.] 98 found: C 68.32 H 6.29 N 12.85, 262368-30-9

The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2004/13099; (2004); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-acetyl-3-(1-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone (1.1 g, 3.07 mmol) and (0.91 g, 3.49 mmol) N-[(4-methyl-piperazin-1-yl)-methylcarbonyl]-N-methyl-p-phenylendiamine are dissolved in 10 ml dimethylformamide and mixed for 1 hour at 80 C. ;After cooling, 0.8 ml piperidine is added and the reaction is further mixed for 2 hours at room temperature. Water is added, the supernatant is removed by suction, and the precipitate is washed again with a small quantity of water. The residue is suspended in 10 ml methanol, the supernatant is removed by suction, and the remaining residue washed with 2 ml cold water and 2 ml diethyl ether. The resulting product is vacuum dried at 110 C. Yield 1.3 g. LCMS: m/z=540 (MH)+. 1HNMR (300 MHz, CDCl3), delta 12.20 (1H, s), 11.10 (1H, s), 7.60 (5H, m), 7.40 (1H, s), 7.20 (3H, m), 6.90-7.00 (2H, d, J=8.7 Hz), 5.80-6.00 (1H, d, J=8.4 Hz), 3.80-3.90 (3H, s), 3.10 (3H, s), 2.70-2.80 (2H, s), 2.20 (11H, s)., 262368-30-9

262368-30-9 N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 21927707, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

Step-2: To a solution of (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (2.6 g, 7.10 mmol) in DMF (5 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (1.94 g, 7.43 mmol) at RT and the reaction mixture was heated to 110 C. and stirred for 1 h. The reaction mixture was allowed to cool to RT, treated with piperidine (3 mL) and stirred for 30 min. The reaction mixture was evaporated and the resultant residue was purified by silica gel column chromatography using 5% CH3OH in dichloromethane as eluent to afford (Z)-methyl 3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenyl)amino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 541.1 (MH+).

262368-30-9, As the paragraph descriping shows that 262368-30-9 is playing an increasingly important role.

Reference：
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; MISHRA, Rama K.; LIM, Dong Sung; OEHLEN, Lambertus J.W.M.; JUNG, Dawoon; US2015/306078; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

To a suspension of methyl (Z)-1-acetyl-3- (ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (6) (500 mg, 1.368 mmol) in DMF (3.5 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (14) (395 mg, 1.505 mmol, 1.1 equiv.) at room temperature. After heating the reaction mixture at 80 oC for 1 h, it was allowed to cool to RT. Piperidine (297 muL, 3.010 mmol, 2.2 equiv.) was then added and stirred for 2 h. Volatiles were removed in vacuo and water was added to the obtained residue and stirred for 15 min. Precipitate was then filtered under suction and cake was washed with water, then with minimum amount of cold methanol, and then ether. The obtained product was purified by column chromatography (neutral Al2O3, 0-10% methanol in CH2Cl2) to afford 532 mg (72%) of target molecule 15. Major conformer 1H NMR (400 MHz, DMSO-d6): delta 12.22 (s, 1H), 10.98 (s, 1H), 7.66-7.47 (m, 5H), 7.42 (s, 1H), 7.24-7.09 (m, 3H), 6.89 (d, J = 8.0 Hz, 2H), 5.83 (d, J = 8.0 Hz, 1H), 3.77 (s, 3H), 3.06 (s, 3H), 2.69 (s, 2H), 2.34-2.06 (brs, 8H), 2.10 (s, 3H). HRMS m/z found 540.2606, calcd for C31H34N5O4 [M+H]+ 540.2605.

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

Step-2: To a solution of (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (2.6 g, 7.10 mmol) in DMF (5 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (1.94 g, 7.43 mmol) at RT and the reaction mixture was heated to 110 C. and stirred for 1 h. The reaction mixture was allowed to cool to RT, treated with piperidine (3 mL) and stirred for 30 min. The reaction mixture was evaporated and the resultant residue was purified by silica gel column chromatography using 5% CH3OH in dichloromethane as eluent to afford (Z)-methyl 3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenyl)amino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 541.1 (MH+).

262368-30-9, As the paragraph descriping shows that 262368-30-9 is playing an increasingly important role.

Reference：
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; MISHRA, Rama K.; LIM, Dong Sung; OEHLEN, Lambertus J.W.M.; JUNG, Dawoon; US2015/306078; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

To a suspension of methyl (Z)-1-acetyl-3- (ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (6) (500 mg, 1.368 mmol) in DMF (3.5 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (14) (395 mg, 1.505 mmol, 1.1 equiv.) at room temperature. After heating the reaction mixture at 80 oC for 1 h, it was allowed to cool to RT. Piperidine (297 muL, 3.010 mmol, 2.2 equiv.) was then added and stirred for 2 h. Volatiles were removed in vacuo and water was added to the obtained residue and stirred for 15 min. Precipitate was then filtered under suction and cake was washed with water, then with minimum amount of cold methanol, and then ether. The obtained product was purified by column chromatography (neutral Al2O3, 0-10% methanol in CH2Cl2) to afford 532 mg (72%) of target molecule 15. Major conformer 1H NMR (400 MHz, DMSO-d6): delta 12.22 (s, 1H), 10.98 (s, 1H), 7.66-7.47 (m, 5H), 7.42 (s, 1H), 7.24-7.09 (m, 3H), 6.89 (d, J = 8.0 Hz, 2H), 5.83 (d, J = 8.0 Hz, 1H), 3.77 (s, 3H), 3.06 (s, 3H), 2.69 (s, 2H), 2.34-2.06 (brs, 8H), 2.10 (s, 3H). HRMS m/z found 540.2606, calcd for C31H34N5O4 [M+H]+ 540.2605.

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

130 g of compound C and 89.9 g of material D were added to the reaction flaskCounted as the molar ratio to match the delivery ratio,Compound C was purified) and 1.8 L of methanol,Under the protection of nitrogen, the temperature was stirred to reflux, 1.5-2h after the reaction solution was dissolved, stirring 9-10h, the sample solution for TLC, no compound C was observed, slightly cool to the reaction system by adding 22g25% aqueous ammonia (mass percentage), continue to warm up to reflux for 2h, there is a clear yellow particles solid precipitation, every 2h sampling for HPLC, detected to the compound E residue of less than 0.1%; the end of the reaction slow mixing speed to room temperature (15-20 ), Filtered, 1.2L of water to wash the filter cake, fully dried to dry the dark yellow powder solid, 60 C blast dry to give compound F 170.5g dark brown powder. The molar yield of the Nidanibu free base (Compound F) was 89%, the purity was 99.8%, and the maximum single impurity was less than 0.1%.

262368-30-9, As the paragraph descriping shows that 262368-30-9 is playing an increasingly important role.

Reference：
Patent; Changzhou Jiade Pharmaceutical Technology Co., Ltd.; Wang Zifu; (7 pag.)CN107011241; (2017); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound (Z) -1- acetyl-3- (methoxy (-2H- tetrahydro-thiopyran-4-yl) methylene) -2-oxo-indole-6-carboxylate Lin ( 600mg, 1.6mmol), 4- (N- methyl-2- (4-methyl-piperazin-1-yl) acetamide) aniline (251mg, 0.96mmol) and potassium hydroxide (50mg, 0.8mmol) was dissolved in 50mL of methanol, the reaction was stirred overnight at 50 deg.] C, the solvent was spin, 50mL of water was added, the mixture with dichloromethane (20mL × 3). the organic phase was dried over anhydrous sodium sulfate, the solvent was spin, the crude product was purified by silica gel column (dichloromethane: methanol = 50: 1) isolated as a dark red solid.(26mg, 3%)

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of methyl (Z)-3-(chloro(4-(hydroxymethyl)phenyl)methylene)-2-oxoindoline- 5-carboxylate (17 mg, 0.05 mmol), N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (15 mg, 0.06 mmol) and TEA (0.1 muL, 0.10 mmol) in EtOH (0.1 muL) was stirred under refluxed for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with dichloromethane/ethanol (50/1, v/v) to obtain the final compound 100 (15 mg, 52% yield): 1H NMR (500 MHz, DMSO-d6) _ 11.97 (s, 1H), 11.13 (s, 1H), 7.57 (d, J = 8.2 Hz, 1H), 7.51 (d, J = 7.8 Hz, 2H), 7.44 (d, J = 7.8 Hz, 2H), 7.13 (d, J = 8.2 Hz, 2H), 6.93 (d, J = 8.3 Hz, 1H), 6.90 (d, J = 8.2Hz, 2H), 6.51 (s, 1H), 5.49 (bs, 1H), 4.64 (s, 2H), 3.63 (s, 3H), 3.05 (bs, 2H), 2.69 (bs, 2H), 2.18 (bs, 6H), 2.10 (s, 3H); 13C NMR (125 MHz, DMSO-d6) _ 170.4, 168.6, 166.4, 157.2, 145.0, 140.4, 139.8, 130.3, 128.3, 127.8, 127.7, 127.0, 125.5, 124.0, 123.6, 121.3, 119.6, 108.8, 97.6, 62.4, 59.2, 54.6, 52.5, 52.4, 51.6, 51.5, 45.8, 36.7; HRMS (ESI-TOF) m/z calcd for C31H32N6O6 [M + H+] 569.2638 found 570.2713.

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of methyl (Z)-3-(chloro(4-(hydroxymethyl)phenyl)methylene)-2-oxoindoline- 5-carboxylate (17 mg, 0.05 mmol), N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (15 mg, 0.06 mmol) and TEA (0.1 muL, 0.10 mmol) in EtOH (0.1 muL) was stirred under refluxed for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with dichloromethane/ethanol (50/1, v/v) to obtain the final compound 100 (15 mg, 52% yield): 1H NMR (500 MHz, DMSO-d6) _ 11.97 (s, 1H), 11.13 (s, 1H), 7.57 (d, J = 8.2 Hz, 1H), 7.51 (d, J = 7.8 Hz, 2H), 7.44 (d, J = 7.8 Hz, 2H), 7.13 (d, J = 8.2 Hz, 2H), 6.93 (d, J = 8.3 Hz, 1H), 6.90 (d, J = 8.2Hz, 2H), 6.51 (s, 1H), 5.49 (bs, 1H), 4.64 (s, 2H), 3.63 (s, 3H), 3.05 (bs, 2H), 2.69 (bs, 2H), 2.18 (bs, 6H), 2.10 (s, 3H); 13C NMR (125 MHz, DMSO-d6) _ 170.4, 168.6, 166.4, 157.2, 145.0, 140.4, 139.8, 130.3, 128.3, 127.8, 127.7, 127.0, 125.5, 124.0, 123.6, 121.3, 119.6, 108.8, 97.6, 62.4, 59.2, 54.6, 52.5, 52.4, 51.6, 51.5, 45.8, 36.7; HRMS (ESI-TOF) m/z calcd for C31H32N6O6 [M + H+] 569.2638 found 570.2713.

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics