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Chemical Structure| 401566-80-1 Chemical Structure| 401566-80-1

Structure of 401566-80-1

Chemical Structure| 401566-80-1

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Product Details of [ 401566-80-1 ]

CAS No. :401566-80-1
Formula : C27H38N6O3S
M.W : 526.69
SMILES Code : O=C(N1[C@H](C(N2CSCC2)=O)C[C@H](N3CCN(C4=CC(C)=NN4C5=CC=CC=C5)CC3)C1)OC(C)(C)C
MDL No. :MFCD22665916

Safety of [ 401566-80-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 401566-80-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 401566-80-1 ]

[ 401566-80-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 401564-36-1 ]
  • 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine [ No CAS ]
  • [ 401566-80-1 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 13h; General procedure: To a solution of 22 (901 mg, 3.00 mmol), 4-phenyl-2-(piperazin-1-yl)thiazole(810 mg, 3.30 mmol) and acetic acid (0.17 mL, 3.0 mmol) in 1,2-dichloroethane (15 mL) was added sodium triacetoxyborohydride (1.27 g, 6.00 mmol) and the mixture stirred at room temperature for 13 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with chloroform/methanol (30:1, v/v) to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-phenylthiazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (1.59 g, 100%) as a pale yellow amorphous.
With sodium tris(acetoxy)borohydride; In toluene; at 5 - 25℃; for 3h; A solution of sodium triacetoxy borohydride (98.8 g) in toluene (300 mL) was added to a mixture of tert-butyl (2S)-4-oxo-2-(1.3-thiazolidin-3- ylcarbonyl)pyrrolidine-1-carboxylate (Formula III, prepared according to the process of Example 3; 100 g) and 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine acetate (Formula VI; 100.7 g) in toluene (800 mL) at 5C to 10C. The reaction mixture was stirred at 20C to 25C for 3 hours. The progress of the reaction was monitored by HPLC. After the reaction was complete, the reaction mixture was quenched with deionized water (600 mL), and stirred for 10 minutes. The reaction mixture was allowed to settle for about 15 minutes. The organic layer was separated and washed with aqueous sodium bicarbonate (60 g sodium bicarbonate in 600 mL deionized water). The organic layer was washed with deionized water (600 mL), and concentrated at a temperature of about 50C under reduced pressure to obtain a residue. The residue was dissolved in isopropyl alcohol (500 mL) to obtain a solution. The solution was concentrated at a temperature of about 50C under reduced pressure, and used as such in the next step.
With sodium tris(acetoxy)borohydride; In tetrahydrofuran; toluene; at 20 - 40℃; The title compound was prepared from 1-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine and the <strong>[401564-36-1](2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester</strong> In a mixture of toluene and tetrahydrofuran, Under the conditions of the presence of sodium triacetoxyborohydride in the catalyst, Degauswise at 20 to 40 C to give intermediate I
  • 2
  • [ 401564-36-1 ]
  • [ 906093-30-9 ]
  • [ 401566-80-1 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In toluene; at 5 - 25℃; for 3h; A solution of sodium triacetoxy borohydride (98.8 g) in toluene (300 mL) was added to a mixture of fert-butyl (2
With sodium tris(acetoxy)borohydride; In toluene; at 5 - 25℃; for 3h; A solution of sodium triacetoxy borohydride (98.8 g) in toluene (300 mL) was added to a mixture of tert-butyl (2S)-4-oxo-2-( i ,3 -thiazolidin-3 -ylcarbonyl)pyrrolidine- i -carboxylate (Formula VI, prepared according to Example 3; iOO g) and i-(3-methyl-i- phenyl-iH-pyrazol-5-yl)piperazine acetate (Formula VII; iOO.7 g) in toluene (800 mL) at 5C to iOC. The reaction mixture was stirred at 20C to 25C for 3 hours. The progress of the reaction was monitored by HPLC. After the reaction was complete, the reaction mixture was quenched with deionized water (600 mL), and then stirred for iO minutes.The reaction mixture was allowed to settle for i 5 minutes. The organic layer was separated, then washed with aqueous sodium bicarbonate (60 g sodium bicarbonate in 600 mL deionized water). The organic layer was washed with deionized water (600 mL), then concentrated at 50C under reduced pressure to obtain a residue. The residue was dissolved in isopropyl alcohol (500 mL) to obtain a solution. The solution wasconcentrated at 50C under reduced pressure, and used as such in the next step.
  • 3
  • [ 401564-36-1 ]
  • 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine acetate [ No CAS ]
  • [ 401566-80-1 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In toluene; at 5 - 25℃; for 3h; A solution of sodium triacetoxy borohydride (98.8 g) in toluene (300 mL) wasadded to a mixture of tert-butyl (28)-4-oxo-2-(1,3-thiazolidin-3-yl carbonyl)pyrrolidine-1-carboxylate (100 g) and 1 -(3-methyl-i -phenyl- 1H-pyrazol-5 -yl)piperazine acetate (Formula III; 100.7 g; prepared according to Example 1) in toluene (800 mL) at 5C to 10C. The reaction mixture was stirred at 20C to 25C for 3 hours. The progress of the reaction was monitored by HPLC. After completion of the reaction, the reaction mixturewas quenched with deionized water (600 mL) and stirred for 10 minutes. The reaction mixture was allowed to settle for about 15 minutes. The organic layer was separated and washed with an aqueous sodium bicarbonate solution (60 g sodium carbonate in 600 mL deionized water). The organic layer was washed with deionized water (600 mL), and concentrated at about 50C under reduced pressure to obtain a residue. The residue was dissolved in isopropyl alcohol (500 mL) and the solution was concentrated at 50C under reduced pressure to obtain tert-butyl (25)-4- [4-(3 -methyl-i -phenyl- 1H-pyrazol-5 -yl)piperazin- i -ylj -2-( i ,3 -thiazolidin-3 -ylcarbonyl)pyrrolidine- i -carboxylate. The residue was used as such in the next step.
With sodium tris(acetoxy)borohydride; In toluene; at 8 - 28℃; for 3h;Large scale; Of 3-methyl-1-phenyl-5- (1-piperazinyl) pyrazoleAcetate (Compound 4a)(25.2 kg), 3-[(2S) -1-t-butoxycarbonyl-4-oxopyrrolidin-2-ylcarbonyl] thiazolidine (Compound 2a)Toluene (425 L) is added to (25.0 kg),Further, a toluene (75 L) slurry of sodium triacetoxyborohydride (23.0 kg) was added at 8 C., followed by stirring at 20 to 28 C. for 3 hours.Water (150 L) was added to the reaction mixture and the layers were separated.The obtained toluene layer was washed with 5 w% sodium bicarbonate water (158 kg) and water (150 L) in this order, and then concentrated under reduced pressure and dried.To the obtained residue, 2-propanol (125 L) was added, and the mixture was again concentrated under reduced pressure and dried.To this residue was added 2-propanol (375 L), the temperature was raised,48 w% hydrobromic acid (42.14 kg) was added dropwise at 75 to 77 C. and then refluxed for 2.5 hours.Cooling the reaction mixture,After inoculating the seed crystal prepared by sampling the reaction mixture at 58 C,1 hour at 58 C, then 1 hour at 33-40 C,Further, crystallization was performed at 17 to 25 C. for 1 hour, and the mixture was allowed to stand overnight.The precipitated crystals were collected by filtration and 2-propanol (50 L)The crystals were washed withThe obtained crystals were dried with hot air (40-47 C.) for 18 hours,{(2S, 4S) -4- [4- (3-Methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-yl} (1,3-thiazolidine- 3-yl) methanone hydrobromide (50.0 kg) was obtained as a crude product.[0089]Ethanol (144 L) was added to the crude product (24.0 kg),After heat dissolution (73 C),Filtered hot and washed with ethanol (24 L).Combine this filtrate and washings,Water (3.4 L) was added at 67 C., followed by crystallization at 49-55 C. for 2 hours and then at 19-25 C. for 1 hour.The precipitated crystals are collected by filtration,Washed with ethanol (24 L).The obtained crystals were dried under reduced pressure at 45 C. for 19 hours,By drying with hot air at 50 C. for 18 hours,{(2S, 4S)-4- [4- (3-Methyl-1-phenyl-1H-Pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-yl} (1,3-thiazolidin-3-yl) methanone2.5 Hydrobromide monohydrate or dihydrate20.9 kg of (Compound 1a) was obtained.(Yield 79%, Yield is a value calculated assuming that it is dihydrate)
 

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