Category: 129779-30-2

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a 20 mL microwave reactor vial was added (3R,5S)-tert-butyl 3,5-dimethylpiperazine- 1 -carboxylate (250 mg, 1.1 67mmol), 1,3 -dibromo-5 -fluorobenzene(592 mg, 2.333 mmol), C52CO3 (950 mg, 2.92 mmol) and toluene (4 mL). The vessel was purged and degassed with N2, then 2,2?-bis(diphenylphosphino)- 1,1 ?-binaphthalene(109 mg, 0.175 mmol) and palladium(II) acetate (52.4 mg, 0.23 3 mmol) were added. The reaction vessel was purged and degassed again. The reaction vessel was capped and the mixture was stirred at 110 C overnight. The reaction mixture was filtered and washed with MeOH and then solvent was removed. The crude was diluted with EtOAc (20 mL),and washed with H20 (20 mL). The orange organic layer was washed with brine, dried over with MgSO4, then concentrated to give crude tert-butyl 4-(3-bromo-5-fluorophenyl) piperazine-1-carboxylate, which was then dissolved in 20% TFA in DCM. The mixture was stirred for 2 hours, concentrated, and then purified by SCX resin (CUBCX1-HL (Benzenesulfonyl, H.L. Resin, 5 g) to provide 1 -((cis)-4-(3 -bromo-5 -fluorophenyl)-3 ,5-dimethylpiperazine, which used directly for next step. LCMS (M+H) = 287.1, 289.1 (1:1 ratio).

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,129779-30-2

Sodium triacetoxyborohydride (0.32 g, 1 .51 mmol) was added to a solution of tert-butyl (3R,5S)-3,5-dimethylpiperazine-i -carboxylate (0.28 g, 1 .30 mmol) and 4-[2-(dimethyl amino)ethoxy]benzaldehyde (Preparation 18a, 0.25 g, 1.29 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was washed with 2M aqueous solution of sodium hydroxide and theorganic layer was separated, dried over magnesium sulfate and the solvent evaporated to dryness. 4M Solution of hydrochloric acid in 1,4-dioxane was added to the residue and the resulting mixture was stirred at room temperature for 2 hours. The solvent was evaporated to dryness to yield the hydrochloride salt of the title compound (299 mg, 45%) as a solid.LRMS (mlz): 292 (M+i).

The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,129779-30-2

Sodium triacetoxyborohydride (0.32 g, 1 .51 mmol) was added to a solution of tert-butyl (3R,5S)-3,5-dimethylpiperazine-i -carboxylate (0.28 g, 1 .30 mmol) and 4-[2-(dimethyl amino)ethoxy]benzaldehyde (Preparation 18a, 0.25 g, 1.29 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was washed with 2M aqueous solution of sodium hydroxide and theorganic layer was separated, dried over magnesium sulfate and the solvent evaporated to dryness. 4M Solution of hydrochloric acid in 1,4-dioxane was added to the residue and the resulting mixture was stirred at room temperature for 2 hours. The solvent was evaporated to dryness to yield the hydrochloride salt of the title compound (299 mg, 45%) as a solid.LRMS (mlz): 292 (M+i).

The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,129779-30-2

Sodium triacetoxyborohydride (0.32 g, 1 .51 mmol) was added to a solution of tert-butyl (3R,5S)-3,5-dimethylpiperazine-i -carboxylate (0.28 g, 1 .30 mmol) and 4-[2-(dimethyl amino)ethoxy]benzaldehyde (Preparation 18a, 0.25 g, 1.29 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was washed with 2M aqueous solution of sodium hydroxide and theorganic layer was separated, dried over magnesium sulfate and the solvent evaporated to dryness. 4M Solution of hydrochloric acid in 1,4-dioxane was added to the residue and the resulting mixture was stirred at room temperature for 2 hours. The solvent was evaporated to dryness to yield the hydrochloride salt of the title compound (299 mg, 45%) as a solid.LRMS (mlz): 292 (M+i).

The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of /er/-butyl (3/^,5.V)-3,5-dimethylpiperazine- 1 -carboxylate (compound Id, CAS: 129779-30-2, PharmaBlock, Catalog: PB125871, 100 mg, 467 pmol) and K2C03 (129 mg, 933 pmol) in MeCN (5 mL) was added l-bromo-4-(bromo methyl) benzene (compound le, CAS: 589-15-1, Accela ChemBio, Catalog: SY001367, 117 mg, 467 pmol). The resultant mixture was heated to 80 C for 14 hrs, then cooled to room temperature. The reaction mixture was filtered and the filter cake was washed with EA (10 mL). The combined filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, 12 g, 10% to 50% EtOAc in PE). The purified intermediate was dissolved in DCM (2 mL) and TFA (0.5 mL) was added. The reaction mixture was stirred at room temperature for 3 hrs, then concentrated to afford a crude compound If, MS: calc?d 283 and 285 [(M+H)+], measured 283 and 285 [(M+H)+], 129779-30-2

The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; QIU, Zongxing; ZHU, Wei; ZOU, Ge; (55 pag.)WO2020/20800; (2020); 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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step A: Preparation of (3R,5S)-tert-butyl 3,4,5-trimethylpiperazine-l- carboxylate: (3R,5S)-tert-Butyl 3,5-dimethylpiperazine-l-carboxylate (1.50 g, 7.00 mmol) was dissolved in 70 mL of methanol. To this was added 37%> aqueous formaldehyde (1.17 mL, 14.0 mmol) and formic acid (1.14 mL, 24.5 mmol). The reaction mixture was heated to 70 C for 24 hours, then concentrated under reduced pressure. The resulting oil was taken up in EtOAc, washed with 10%> aqueous potassium carbonate, dried over sodium sulfate and concentrated to give 1.17 g (73%>) of the title compound., 129779-30-2

As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference：
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; DELISLE, Robert Kirk; HICKEN, Erik James; KENNEDY, April L.; MARESKA, David A.; MARMSATER, Fredrik P.; MUNSON, Mark C.; NEWHOUSE, Brad; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2012/82689; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1,3-dibromobenzene (1.10 g, 4.67 mmol), (cis)-tert-butyl 3,5- dimethylpiperazine- 1 -carboxylate (0.5 g, 2.33 mmol) and 2-dicyclohexylphosphino-2?,6?- dimethoxy- 1,1 ?-biphenyl (47.9 mg, 0.117 mmol) in THF (15 mL) in a pressure reactionvial was purged with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (42.7 mg,0.047 mmol) was added, followed by lithium bis(trimethylsilyl)amide (7.0 mL, 7.0 mmol,1 N in THF). The mixture was purged with nitrogen for several mm and then capped andheated at 70 C for 2.5 h. The reaction mixture was cooled and quenched with aq.NaHCO3, then diluted with 75 mL of EtOAc, washed with H20, brine, dried andconcentrated. The residue was purified on silica gel, with a linear gradient of 0-100%EtOAc/hexanes to give (cis)-tert-butyl 4-(3 -bromophenyl)-3 ,5 -dimethylpiperazine- 1- carboxylate (0.505 g) as an oil. LCMS, M+H = 369.2/37 1.2 Method G. Rt. 3.55 mm.

129779-30-2, The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1,3-dibromobenzene (1.10 g, 4.67 mmol), (cis)-tert-butyl 3,5- dimethylpiperazine- 1 -carboxylate (0.5 g, 2.33 mmol) and 2-dicyclohexylphosphino-2?,6?- dimethoxy- 1,1 ?-biphenyl (47.9 mg, 0.117 mmol) in THF (15 mL) in a pressure reactionvial was purged with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (42.7 mg,0.047 mmol) was added, followed by lithium bis(trimethylsilyl)amide (7.0 mL, 7.0 mmol,1 N in THF). The mixture was purged with nitrogen for several mm and then capped andheated at 70 C for 2.5 h. The reaction mixture was cooled and quenched with aq.NaHCO3, then diluted with 75 mL of EtOAc, washed with H20, brine, dried andconcentrated. The residue was purified on silica gel, with a linear gradient of 0-100%EtOAc/hexanes to give (cis)-tert-butyl 4-(3 -bromophenyl)-3 ,5 -dimethylpiperazine- 1- carboxylate (0.505 g) as an oil. LCMS, M+H = 369.2/37 1.2 Method G. Rt. 3.55 mm.

129779-30-2, The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[20371 Step 2: Synthesis of (3R.5S?)-tert-butvl4-(4-((E?)-3-methoxv-3-oxoprop- 1-en-i -vl?)benzvl?)-3.5-dimethvlpiperazine- 1 -carboxvla te[20381 (3R,55)-tert-butyl 3 ,5-dimethylpiperazine- 1 -carboxylate (formula 8-i, 5.000 g, 23.332 mmol), methyl 3-(4-bromomethyl)cinamate (formula 8-4, 5.952 g, 23.332 mmol) and Cs2CO3 (15.204 g, 46.664 mmol) were mixed in acetonitrile (150 mL) at room temperature, and the mixture was heated under reflux, and then cooled to room temperature. The reaction mixture was filtered through a paper filter to remove solids, and the filtrate was concentrated under reduced pressure to remove the solvent. The concentrate was purified by column chromatography (silicon dioxide, 80 g cartridge; ethyl acetate/hexane = from 0 % to 20 %) and concentrated to afford the desired compound (6.800 g, 75.0 %) as a yellow oil.

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference：
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; SONG, Hyeseung; LEE, Changgon; KWAK, Dalyong; LEE, Jaeyoung; BAE, Suyeal; KIM, Yuntae; BAE, Daekwon; HA, Nina; BAE, Miseon; KIM, Jihyun; WO2015/137750; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[20371 Step 2: Synthesis of (3R.5S?)-tert-butvl4-(4-((E?)-3-methoxv-3-oxoprop- 1-en-i -vl?)benzvl?)-3.5-dimethvlpiperazine- 1 -carboxvla te[20381 (3R,55)-tert-butyl 3 ,5-dimethylpiperazine- 1 -carboxylate (formula 8-i, 5.000 g, 23.332 mmol), methyl 3-(4-bromomethyl)cinamate (formula 8-4, 5.952 g, 23.332 mmol) and Cs2CO3 (15.204 g, 46.664 mmol) were mixed in acetonitrile (150 mL) at room temperature, and the mixture was heated under reflux, and then cooled to room temperature. The reaction mixture was filtered through a paper filter to remove solids, and the filtrate was concentrated under reduced pressure to remove the solvent. The concentrate was purified by column chromatography (silicon dioxide, 80 g cartridge; ethyl acetate/hexane = from 0 % to 20 %) and concentrated to afford the desired compound (6.800 g, 75.0 %) as a yellow oil.

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference：
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; SONG, Hyeseung; LEE, Changgon; KWAK, Dalyong; LEE, Jaeyoung; BAE, Suyeal; KIM, Yuntae; BAE, Daekwon; HA, Nina; BAE, Miseon; KIM, Jihyun; WO2015/137750; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics