Analyzing the synthesis route of 106261-48-7

The synthetic route of 106261-48-7 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.106261-48-7,4-((4-Methylpiperazin-1-yl)methyl)benzoic acid,as a common compound, the synthetic route is as follows.

Comparative Example 21 : LambdaT-(5-bromo-2-cyano-4-pyrimidinyl)-Lambdar-(2,2-dimethylpropyl)- 4-[(4-methyl-1-piperazinyl)methyl]benzohydrazide trifluoroacetate.Intermediate 21 (1 g, 4.3 mmol) was dissolved in thionyl chloride (5 ml). The reaction mixture was stirred at room temperature for 17 hours. The solvent was evaporated in vacuo and the acid chloride was used without any further purification.To a stirred solution of Intermediate 19 (200 mg, 0.70 mmol) in pyridine (1 mL) and DIPEA (5 mL), potassium carbonate (193 mg, 1.40 mmol) and previously obtained acid chloride(443 mg, 1.75 mmol) were added and the resulting reaction mixture was stirred at room temperature for 17 hours. The solvent was evaporated in vacuo and the crude reaction mixture was purified by flash chromatography (silica gel, dichloromethane:methanol). The solid was repurified by HPLC (H2O:ACN) to give the title compound. 1H NMR (300 MHz, DMSO) delta ppm: 11.33 (s, 1H), 8.64 (s, 1 H), 7.91 (d, 2H), 7.49 (d, 2H), 3.72 (s, 2H), 3.37(m, 2H), 3.25-2.81 (br, 6H), 2.78 (s, 3H) 0.99 (s, 9H). [ES+ MS] m/z 500 (MH+)., 106261-48-7

The synthetic route of 106261-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/25774; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

106261-48-7, As the paragraph descriping shows that 106261-48-7 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.106261-48-7,4-((4-Methylpiperazin-1-yl)methyl)benzoic acid,as a common compound, the synthetic route is as follows.

Intermediate 42: W-(5-bromo-2-cyano-4-pyrimidinyl)-4-[(4-methyl-1 -piperazinyl) methyl]-W-(2-methylpropyl)benzohydrazide trifluoroacetate. Preparation of 4-[(4-methyl-1-piperazinyl)methyl]benzoyl chloride.Intermediate 38 (500 mg, 2.13 mmol) was dissolved in thionyl chloride (5 ml). The reaction mixture was refluxed for 6 hours. The solvent was evaporated in vacuo and the crude product was used without any further purification.To a stirred solution of Intermediate 41 (200 mg, 0.74 mmol) in pyridine (10 ml_), a mixture of the previously prepared acid chloride (539 mg, 2.13 mmol) and DIPEA (0.26 ml_, 1.48 mmol) in dry THF (10 ml.) was added and the resulting reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo and the crude reaction mixture was purified by flash chromatography (silica gel, dichloromethane:methanol). The solid was repurified by HPLC (H2O, 0.1%TFA:ACN) to give the title compound. 1H NMR (300 MHz, DMSO) delta ppm: 11.36 (s, 1 H), 8.64 (s, 1 H), 7.92 (d, 2H), 7.48 (d, 2H), 3.98 (m, 1 H), 3.73 (s 2H), 3.38 (m, 4H), 3.02 (m 4H), 2.78 (s, 3H) 2.42 (m, 1 H), 2.05 (m, 1 H), 0.94 (d, 6H). [ES+ MS] m/z 486 (M)+.

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Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107368; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

106261-48-7, As the paragraph descriping shows that 106261-48-7 is playing an increasingly important role.

106261-48-7, 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Comparative Example 39: N’-(5-bromo-2-cyano-4-pyrimidinyl)-N’-(2,2-dimethylpropyl)-4-[(4-methyl-1-piperazinyl)methyl]benzohydrazide trifluoroacetate. [Show Image] Intermediate 49 (1 g, 4.3 mmol) was dissolved in thionyl chloride (5 ml). The reaction mixture was stirred at room temperature for 17 hours. The solvent was evaporated in vacuo and the acid chloride was used without any further purification.

106261-48-7, As the paragraph descriping shows that 106261-48-7 is playing an increasingly important role.

Reference:
Patent; GLAXO GROUP; EP1918284; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Some tips on 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

Big data shows that 106261-48-7 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.106261-48-7,4-((4-Methylpiperazin-1-yl)methyl)benzoic acid,as a common compound, the synthetic route is as follows.

A mixture of compound 5 (20 mg, 0.05 mmol), 4- (N-methyl-piperazyl)- methyl-benzoic acid (14 mg, 0.06 mmol), 0- (7-azabenzotriazol-1-yl)-N, N, N’, N’- tetramethyl-uronium hexafluorophosphate (23 mg, 0.06 mmol) and diisopropylethylamine (8 mg, 0.06 mmol) in methylene chloride (2 mL) is stirred at room temperature over night. LCMS purification afforded N-(3-{2-[6-(3-dimethylamino-phenylamino)-pyrimidin-4-yl]- phenylamino}-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide (9.2 mg, 30 % yield): ‘H NMR 400 Hz (CDCl3) b 2.51 (s, 3H), 2. 61 (br, 4H), 2.78 (br, 4H), 2.97 (s, 6H), 3.58 (s, 2H), 6.57 (m, 1H), 6.68 (m, 2H), 6.84 (m, 1H), 6.97 (m, 1H), 7.10 (m, 2H), 7.18 (m, 1H), 7.26 (m, 2H), 7.40 (d, J = 8.12 Hz, 2H), 7.46 (d, J = 8.12 Hz, 2H), 7.54 (s, br, 1H), 7.79 (d, J = 8. 14 Hz, 2H), 7.86 (s, 1H), 8.69 (s, 1H); MS m/z (M+H) 613.30., 106261-48-7

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Reference:
Patent; IRM LLC; WO2005/33086; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Some tips on 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

Big data shows that 106261-48-7 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.106261-48-7,4-((4-Methylpiperazin-1-yl)methyl)benzoic acid,as a common compound, the synthetic route is as follows.

A 50-mL, three-neck, round bottomed flask equipped with a magnetic stirrer was charged with 4- Methyl-N1-(5-thiophen-3-yl-pyrimidin-2-yl)-benzene-1,3-diamine (371 mg, 1.31 mmol), 4-(4-Methyl- piperazin-1-y(methyl)-benzoic acid (402 mg, 1.31 mmol), N,N-diisopropylethylamine (171 mg, 1.57 mmol), and anhydrous DMF (3.0 mL). To the resulting mixture were added 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (302 mg, 1.57 mmol) and 1-hydroxy-7-azabenzotriazole (89 mg, 0.655 mmol). After stirring for 20 h at ambient temperature, the reaction mixture was evaporated to dryness, purified by column chromatography (methanol/methylene chloride), and then triturated with acetonitrile, filtered and the filter cake dried under vacuum affording an 72% yield of Example 40 as a white solid. (at)HNMR (400 MHz, DMSO-de) No. 8.76 (s, 2H), 7.99 (d, 2H), 7.85 (s, 1 H), 7.66 (s, 1 H), 7.53 (m, 4H), 7.43 (d, 1 H), 7.23 (d, 1 H), 3.70 (m, 2H), 2.93 (m, 4H), 2.69 (m, 4H), 2.58 (s, 3H), 2.29 (s, 3H). MS m/z 499 [M++1, 106261-48-7

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Reference:
Patent; SUGEN, INC.; WO2005/113548; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

106261-48-7, Big data shows that 106261-48-7 is playing an increasingly important role.

106261-48-7, 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00130] To a solution of 5-(3-amino-phenylamino)-l,3-dihydro-indol-2-one (20 mg, 0.083 mmol) in DMF (2ml) is added 4-(4-methyl-piperazin-l-ylmethyl)-benzoic acid (31 mg, 0.1 mmol), N,N-diisopropylethylamin (54 mg, 0.42 mmol), EDCI (32 mg, 0.17 mmol) and HOBt (11 mg, 0.083 mmol). The reaction is stirred for 12 hours and EPO concentrated. The residue is purified by HPLC to afford the desired compound: LC-MS: 456.2 (MH+).

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Reference:
Patent; IRM LLC; WO2006/52936; (2006); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 106261-48-7

As the paragraph descriping shows that 106261-48-7 is playing an increasingly important role.

106261-48-7, 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 12: 4-( 4-Methvl-piperazin-1-vlmethvl)-N-r 4-(5-thiophen-3-vl-pvrimidin-2-vlamino )-phenvll- benzamide; 4-Chloromethylbenzoic acid (1.7 g, 10 mmol) and 2.78 mL (20 mmol) of triethylamine in 50 mL of dimethylformamide was stirred with 1.22 mL (11 mmol) of N-methylpiperazine overnight at room temperature. The white solid was collected by vacuum filtration and washed with dichloromethane. The combined filtrates were rotary evaporated to dryness to give 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid. N-(5-Thiophen-3-yl-pyrimidin-2-yl)-benzene-1 ,4-diamine (55 mg, 0.20 mmol), triethylamine (0.112 mL, 0.80 mmol), BOP reagent (265 mg, 0.6 mmol) and 93 mg (0.4 mmol) of 4-(4-methyl-piperazin-1- ylmethyl) -benzoic acid in 1 mL of dimethylformamide were stirred overnight at room temperature. The solvent was evaporated and the residue purified by flash chromatography eluting with dichloromethane:methanol 20: 1 and then dichlormehane:methanol 15: 1 to give 4-(4-methyl-piperazin-1- ylmethyl)-N[4-(5-thiophen-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide. H-NMR (dimethylsulfoxide-d6) 8 10.03 (s, 1 H), 9.65 (s, 1 H), 8.80 (s, 2H), 7.85 (m, 3H), 7.67 (m, 2H), 7.63 (m, 2H), 7.57 (d, 1 H), 7.38 (d, 2H), 3.45 (s, 2H), 2.50 (m, 8H), 2.30 (s, 3H). MS (m/z) 485 [M+1]., 106261-48-7

As the paragraph descriping shows that 106261-48-7 is playing an increasingly important role.

Reference:
Patent; SUGEN, INC.; WO2005/113548; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid

Big data shows that 106261-48-7 is playing an increasingly important role.

106261-48-7, 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The mixture containing compound 6 (2.51 mmol), methanol (5.0 mL), 2 M NaOH (1.6 mL) was stirred at room temperature for 4 h, concentrated under reduced pressure and acidified with concentrated hydrochloric acid to pH 2. The aqueous phase was concentrated to dryness under reduced pressure to afford the crude 4-aminomethylbenzoic acid (containing sodium chloride) which was carried on the next step without further purification. The 4-aminomethylbenzoic acid (2.51 mmol) and 2 drops of DMF were added to thionyl chloride (10 mL). The mixture was refluxed for2 h. The volatile was removed under reduced pressure to give a pale yellow solid which was then dissolved in anhydrous THF (10 mL) and was added dropwise to a suspension of sodium azide (0.24 g, 3.77 mmol) in 10 mL of THF/H2O (4:1, v/v) at 0-5C. Then the mixture was stirred at room temperature overnight and THF was removed under reduced pressure. The aqueous phase was extracted with dichloromethane (20 mL 3). The organic layerwas combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to produce compounds 7a-7f as yellow or brown oil., 106261-48-7

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Reference:
Article; Zuo, Sai-Jie; Zhang, Sai; Mao, Shuai; Xie, Xiao-Xiao; Xiao, Xue; Xin, Min-Hnag; Xuan, Wei; He, Yuan-Yuan; Cao, Yong-Xiao; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 179 – 190;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Some tips on 106261-48-7

The synthetic route of 106261-48-7 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.106261-48-7,4-((4-Methylpiperazin-1-yl)methyl)benzoic acid,as a common compound, the synthetic route is as follows.

Example 3: Preparation of 4-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamide Method D; To a flask was added 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (3.2 g) and SOCl2 (100 mL) and the solution was refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to give a solid, which was used for the next step directly. To the above carboxylic acid chloride was dropped a clear solution of N-(5-amino-2-methylpyridin-3-yl)-4-(3-pyridyl)pyrimidin-2-amine (3.0 g) in pyridine (80 mL) and the solution was stirred at room temperature overnight. The solvent was removed under reduced pressure, and then the residue was added with chloroform (100 mL) and water (100 mL) for extraction. The organic phase was dried, filtrated, concentrated, and purified through column chromatography to give 4-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamide (4.2 g)., 106261-48-7

The synthetic route of 106261-48-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sun, Piaoyang; EP1840122; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 106261-48-7

106261-48-7, The synthetic route of 106261-48-7 has been constantly updated, and we look forward to future research findings.

106261-48-7, 4-((4-Methylpiperazin-1-yl)methyl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method E; To a flask was added 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (3.2 g), dicyclohexylcarbodiimide (3.0 g), N-(5-amino-2-methylpyridin-3-yl)-4-(3-pyridyl)pyrimidin-2-amine (3.0 g) and CH2Cl2 (100 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtrated and the filtrate was washed with water (100 mL ¡Á 2), dried, filtrated, concentrated, and purified through column chromatography to give 4-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamide (4.0 g).

106261-48-7, The synthetic route of 106261-48-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sun, Piaoyang; EP1840122; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics