Category: 74879-18-8

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74879-18-8

Example 24 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-9-methyl-7-[(3S)-3-methylpiperazin-l- yl]pyrido[l,2-a]pyrimidin-4-one In a sealed tube, 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-7-fluoro-9-methyl- pyrido[l,2-a]pyrimidin-4-one (Intermediate 4; 50 mg, 0.155 mmol) and (S)-2-methylpiperazine (62 mg, 0.619 mmol, 4.0 eq.) were stirred in DMSO (2 mL) at 125C overnight. The solvent was removed under high vacuum. The residue was taken up in CH2CI2 and washed with an aqueous saturated solution of NaHC03. The organic layer was separated and dried over Na2S04 and concentrated in vacuo. The crude was purified by column chromatography (S1O2, CH2Cl2/MeOH=95/5 to 90/10) to afford the title product (45 mg, 72%) as a light yellow solid. MS m/z 404.3 [M+H+].

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PTC THERAPEUTICS INC.; RATNI, Hasane; GREEN, Luke; NARYSHKIN, Nikolai A.; WEETALL, Marla L.; (80 pag.)WO2015/173181; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

In a sealed tube, 7-fluoro-9-methyl-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one (Intermediate 3; 250 mg, 0.808 mmol), and (S)-2-methylpiperazine (405 mg, 4.04 mmol, 5.0 eq.) were stirred in DMSO (6 mL) and heated at 130 C. overnight. The solvent was removed under high vacuum. The residue was taken up in CH2Cl2 and washed with an aqueous saturated solution of NaHCO3. The organic layer was separated and dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography (SiO2, CH2Cl2/MeOH=95/5 to 85/15) to afford the title product (135 mg, 43%) as a light yellow solid. MS m/z 390.3 [M+H+].

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; PTC Therapeutics, Inc.; Ratni, Hasane; Green, Luke; Weetall, Maria L.; Naryshkin, Nikolai A.; (33 pag.)US2019/315773; (2019); 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.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 68 (3S)-1-{[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]methyl}-3-methylpiperazine To a solution of 6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde (250 mg) in tetrahydrofuran (10 mL) was added (2S)-2-methylpiperazine (270 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (230 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (111 mg, yield 38%) as a colorless amorphous solid. MS:549(MH+). 1H NMR (300 MHz, CDCl3) 50.98 – 1.03 (2 H, m), 1.05 (3 H, d, J=6.2 Hz), 1.29 – 1.49 (5 H, m), 1.52 – 1.70 (3 H, m), 1.82 – 1.97 (2 H, m), 2.05 – 2.15 (2 H, m), 2.36 – 2.49 (1 H, m), 2.66 – 2.79 (2 H, m), 2.81 – 3.05 (3 H, m), 3.19 – 3.36 (2 H, m), 3.40 – 3.50 (2 H, m), 3.84 – 4.00 (2 H, m), 4.12 – 4.23 (1 H, m), 6.15 (1 H, t, J=3.0 Hz), 6.63 (1 H, dd, J=2.4, 3.5 Hz), 7.40 (2 H, d, J=8.3 Hz), 7.44 – 7.50 (1 H, m), 7.52 – 7.63 (1 H, m), 7.75 – 7.88 (2 H, m), 8.29 (1 H, d, J=1.5 Hz), 9.22 (1 H, brs)., 74879-18-8

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); 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.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.,74879-18-8

EXAMPLE 213A (3S)-3-methyl-1-(2-pyridinyl)piperazine A solution of (S)-(+)-2-methylpiperazine (0.50 g, 0.005 mol, CAS 74879-18-8, Aldrich 39,717-2, 99%) and 2-bromopyridine (5 mL, 0.05 mol) was heated to 120 C. for 14 hours. The reaction mixture was cooled to 23 C. and partitioned between ethyl acetate and water. The layers were separated, and the water layer extracted twice more with ethyl acetate. The aqueous phase was adjusted to pH~11 with a solution of saturated sodium bicarbonate and solid sodium carbonate. Sodium chloride was added, and the saturated aqueous solution was extracted with ethyl acetate (2*) and dichloromethane (2*). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 0.6 g (67% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) delta1.02 (d, J=6.0 Hz, 3H), 2.27 (dd, J=12, 10 Hz, 1H), 2.67 (m, 3H), 2.92 (m, 1H), 4.07 (m, 2H), 6.58 (dd, J=8, 6 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 7.49 (m, 1H), 8.08 (m, 1H); MS (ESI) m/e 178 (M+H)+.

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; Bhatia, Pramila A.; Daanen, Jerome F.; Hakeem, Ahmed A.; Kolasa, Teodozyj; Matulenko, Mark A.; Mortell, Kathleen H.; Patel, Meena V.; Stewart, Andrew O.; Wang, Xueqing; Xia, Zhiren; Zhang, Henry Q.; US2004/29887; (2004); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74879-18-8

Example 5 (0326) [0227] Compound 154 was prepared according to the reaction scheme in Figures 3 and 4. (0327) [0228] In a first step, compound 40 was prepared from compound 30 as follows: (0328) (0329) 30 40 (0330) [0229] Water (500 g, 5 w/w%) was charged to a reaction flask. Compound 30 (2- methylpiperazine) (100 g, 998.4 mmol, 1 eq.) was charged to the reaction flask with agitation. HC1 (36% aqueous, 102.1 g, 1008 mmol, 1.01 eq.) and methanol (200 g) were charged to the reaction flask with agitation. A solution of Boc20 (222 g, 1008 mmol, 1.01 eq.) in methanol (200 g) was added dropwise to the reaction flask at 15 to 25 C followed by stirring for 18 hours at 20 to 30C. The flask contents were evaporated to dryness in vacuo at 40 to 50C to form a residue. Water (500 g) was added to the residue and the mixture was stirred for 1 hours. The mixture was filtered and the collected solids were washed with water (50 g). The aqueous filtrate was extracted with ethylacetate (500 mL). The extracted aqueous phase was adjusted to a pH in excess of 12 with 30% NaOH and was then extracted with ethylacetate (500 mL) three times. The organic phase was washed with brine (500 g) twice and was then dried with anhydrous Na2S04. The dried mixture was filtered and the collected solids were rinsed with ethylacetate (100 mL). The filtrate was concentrated to dryness in vacuo at 50 to 60C and further concentrated under high vacuum (5 mm Hg) at 65 to 75C for 3 hours to yield compound 40 (tert-butyl 3-methylpiperazine-l-carboxylate). The purity of compound 40 was 97.7 area%, the assay was 95.9% and the yield was 76.4%.

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BEAUDRY, Danial; CRAVILLION, Theresa; GOSSELIN, Francis; LIM, Ngiap-Kie; MALHOTRA, Sushant; TIAN, Qingping; ZHANG, Haiming; GMEHLING, Alexander; FETTES, Alec; BACHMANN, Stephan; (130 pag.)WO2018/109050; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74879-18-8

Step B: The alkyne intermediate obtained in Step A (9.33 g, 30.0 mmol) was mixed with (S)-2-methylpiperazine (3.60 g, 36.0 mmol), Pd2dba3 (0.27 g, 0.6 mmol), JohnPhos (0.18 g, 0.6 mmol) and Cs2C03 (13.7 g, 42.0 mmol). The reaction system was purged with argon three times and the solvent DME (60 mL) was added. The suspension was then stirred at 80 C for 4 hours. LC/MS analysis of an aliquot of the reaction mixture revealed a complete consumption of the starting bromide. Solvent was removed on a rotovap and the residue was chromatographed (silica gel, ethyl acetate in dichloromethane 0-50 %) to give (S)-methyl 5-(3-methylpiperazin-l- yl)-2-((trimethylsilyl)ethynyl)benzoate as a brown oil (7.56 g, 79%). MS m/z 331.1 [M+H]+.

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; DAKKA, Amal; KARP, Gary Mitchell; LI, Chunshi; NARASIMHAN, Jana; NARYSHKIN, Nikolai; WEETALL, Maria L.; WELCH, Ellen; ZHAO, Xin; WO2013/112788; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Alternative preparation of 3-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine: Example 2aPyrazolo[1,5-a]pyrimidine-3-carboxylic acid (11.73 g, 71.9 mmol) was suspended in thionyl chloride (36 mL, 493 mmol) and heated at 60 C. for 2 h. Formation of the acyl chloride was monitored as follows: a sample of the reaction mixture was evaporated and added to MeOH and formation of the corresponding methyl ester was detected by UPLC. Then thionyl chloride was removed under reduced pressure to obtain pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (14 g) as a yellow solid.(2S)-2-methylpiperazine (6 g, 59.9 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled down to 0 C., aqueous sodium hydroxide (3M, 39.9 mL, 120 mmol) was added and stirred for 10 min. Then 4-(trifluoromethyl)benzenesulfonyl chloride (16.12 g, 65.9 mmol) (dissolved in 50 ml of THF) was added drop-wise, stirring the reaction mixture for 1 h. THF was removed under reduced pressure, the aqueous phase was diluted with water (200 ml) and extracted with DCM (2¡Á300 ml). The organic layer was concentrated under reduced pressure and the oily residue was suspended with HCl 1M (200 ml) and washed with DCM in order to extract impurities. NaOH 3M was added to the aqueous layer to reach pH 10 then the mixture was diluted with THF (200 ml), the mixture was cooled down to 0 C.The pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (14 g) was suspended in THF (80 ml) and added portion-wise to the above mixture, maintaining the pH>9 by adding NaOH 3M, and then the mixture was stirred overnight. THF was removed from the mixture under reduced pressure and the resulting suspension was extracted with DCM (2¡Á300 ml). The organic layer was washed with HCl 0.1 M, dried over Na2SO4 and concentrated to dryness to obtain the crude material (21.7 g) as foam. The crude material was re-dissolved in DCM (100 ml) and evaporated to minimum volume to obtain an oily residue, ethyl ether was added (80 ml) with stirring. A solid crashed out from the solution and was recovered by filtration, washing with ethyl ether before drying to give the title compound (20.06 g).m/z (API-ES) 454 [M+H]+ 1H NMR (400 MHz, CDCl3) delta ppm 1.48 (d, J=7.2 Hz, 3H), 2.56 (td, J=11.6, 3.2 Hz, 1H), 2.69 (dd, J=11.6, 3.6 Hz, 1H), 3.50 (m, 1H), 3.64 (d, J=11.6 Hz, 1H), 3.82 (d, J=11.2 Hz, 1H), 4.25 (m, 1H), 4.78 (m, 1H), 6.97 (dd, J=7.2, 4.0 Hz, 1H), 7.85 (d, J=8.4 Hz, 2H), 7.91 (d, J=8.4 Hz, 2H), 8.39 (s, 1H), 8.59 (dd, J=4.0, 1.6 Hz, 1H), 8.73 (dd, J=7.2, 1.6 Hz, 1H)., 74879-18-8

The synthetic route of 74879-18-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Heer, Jag Paul; Norton, David; Ward, Simon E.; US2010/16330; (2010); 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.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Step B tert-Butyl (3S)-3-methylpiperazine-1-carboxylate To a solution of (2S)-2-methylpiperazine (20.0 g, 0.200 mol) in methylene chloride (300 mL) and triethylamine (20.4 g, 0.202 mol) was added dropwise a solution of di-tert-butyl dicarbonate (44.0 g, 0.202 mol) in CH2Cl2 (100 mL) over 5 hrs. The mixture was washed with water, brine, and then dried over MgSO4 and concentrated. Column chromatography on silica (10-20% MeOH in EtOAc) afforded 32.0 g (80%) of the title compound as an oil. Step C tert-Butyl (3S)-4-(5-bromo-2,3-dihydro-1H-inden-1-yl)-3-methylpiperazine-1-carboxylate, 74879-18-8

The synthetic route of 74879-18-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

74879-18-8, To a stirred solution of (2S)-2-methylpiperazine (0.30 g, 2.1 mmol) in DMA (6 mL), 6-chloropyridine-3-carbonitrile (0.29 g, 2.3 mmol) and K2C03 were added. The resultantreaction mixture was heated to 60 C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was diluted with cold water (20 mL) and extractedwith EtOAc (3 x 25 mL). The combined organic extracts were washed with cold water (20mL) and brine (2 x 20 mL). The organic layer was separated, dried over Na2S04 andconcentrated under reduced pressure to give the crude residue which was purified by columnchromatography (100-200 silica gel, 10 g, 10% MeOH-DCM) to furnish 6-[(3S)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile (0.29 g, 67%) as an off-white solid.LCMS: m/z: 203.4 [M+Ht.

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

74879-18-8, A dimethyl sulfoxide suspension (5 ml) of 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine (476.1 mg, 1.23 mmol) and (2S)-2-methylpiperazine (616.4 mg, 6.15 mmol) was heated at 100 C. to dissolve and the resulting mixture was stirred at 85 C. for 18.5 hours. (2S)-2-Methylpiperazine (123.3 mg, 1.23 mmol) was added and the resulting mixture was further stirred at 85 C. for 5.5 hours, left standing to cool, poured into methylene chloride-methanol (10:1), and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride_methanol=32:1 to 9:1) to give the title compound (516.0 mg, 93%) as a pale yellow solid.1H-NMR (CDCl3) delta: 0.48-0.57 (4H, m), 1.15 (3H, d, J=6.87 Hz), 1.31-1.41 (1H, m), 2.71 (1H, t, J=11.17 Hz), 2.98-3.15 (4H, m), 3.36-3.45 (2H, m), 3.83-3.89 (4H, m), 3.90-4.02 (2H, m), 4.18-4.41 (4H, brm), 5.60 (2H, brs), 9.24 (2H, s).

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2010/130492; (2010); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics