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Chemical Structure| 1217728-72-7 Chemical Structure| 1217728-72-7

Structure of 1217728-72-7

Chemical Structure| 1217728-72-7

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Product Details of [ 1217728-72-7 ]

CAS No. :1217728-72-7
Formula : C11H22N2O3
M.W : 230.30
SMILES Code : O=C(N1[C@H](COC)CNCC1)OC(C)(C)C
English Name :(S)-tert-Butyl 2-(methoxymethyl)piperazine-1-carboxylate
MDL No. :MFCD11112289
InChI Key :ODOJNXXZXCRBCC-VIFPVBQESA-N
Pubchem ID :53484854

Safety of [ 1217728-72-7 ]

Application In Synthesis of [ 1217728-72-7 ]

* 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 [ 1217728-72-7 ]

[ 1217728-72-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 2380844-88-0 ]
  • [ 1217728-72-7 ]
YieldReaction ConditionsOperation in experiment
99% With 10% Pd/C; hydrogen In methanol at 20℃; for 4h; Step 2: Synthesis of Compound F9 Compound F9-1 (2.51 g, 6.89 mmol), 10% Pd/C (251 mg) and methanol (20 mL) were sequentially added to a dry reaction flask, and the mixture was stirred at room temperature for 4 h under a hydrogen atmosphere.Filtered, the filter cake was washed with dichloromethane (20 mL), the filtrate was concentrated under reduced pressure,The title compound was obtained as a white solid (1.58 g, 99%).
  • 2
  • [ 385802-84-6 ]
  • [ 1217728-72-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / -20 °C 1.2: 5 h / 20 °C 2.1: 10% Pd/C; hydrogen / methanol / 4 h / 20 °C
  • 3
  • [ 2573869-16-4 ]
  • [ 1217728-72-7 ]
  • [ 2935393-21-6 ]
YieldReaction ConditionsOperation in experiment
61.6 % With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In N,N-dimethyl acetamide at 20 - 100℃; 397.1 Step 1: tert-butyl (S)-2-(methoxymethyl)-4-((R, E) -1 1, 2 6, 7-trimethyl-3-oxo-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphane-5 6-yl) piperazine-1-carboxylat e [1484] [1485] To a mixture of (R, E) -5 6-bromo-1 1, 2 6, 7-trimethyl-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphan-3-one (0.5 g, 0.98 mmol), tert-butyl (S)-2-(methoxymethyl) piperazine-1-carboxylate (393 mg, 1.96 mmol), Pd 2 (dba) 3 (89 mg, 0.1 mmol), Ruphos (91 mg, 0.2 mmol), NaO tBu (283 mg, 2.94 mmol) in DMA (10 mL) was stirred at 100 °C for 4 hrs. After cooling to r.t, the reaction was quenched with sat. NH 4Cl solution (15 mL), the resulting mixture was extracted with DCM (20 mL x 3). The combined organic phase was washed with brine (20 mL), dried over Na 2SO 4, filtered and concentrated in vacuum. The residue was purified by silica gel column (DCM : CH 3OH = 20: 1) to afford tert-butyl (S)-2-(methoxymethyl)-4-((R, E) -1 1, 2 6, 7-trimethyl-3-oxo-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphane-5 6-yl) piperazine-1-carboxylate (380 mg, 61.6%). [M+H] + = 659.4. [1486]
61.6 % With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In N,N-dimethyl acetamide at 20 - 100℃; 397.1 Step 1: tert-butyl (S)-2-(methoxymethyl)-4-((R, E) -1 1, 2 6, 7-trimethyl-3-oxo-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphane-5 6-yl) piperazine-1-carboxylat e [1484] [1485] To a mixture of (R, E) -5 6-bromo-1 1, 2 6, 7-trimethyl-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphan-3-one (0.5 g, 0.98 mmol), tert-butyl (S)-2-(methoxymethyl) piperazine-1-carboxylate (393 mg, 1.96 mmol), Pd 2 (dba) 3 (89 mg, 0.1 mmol), Ruphos (91 mg, 0.2 mmol), NaO tBu (283 mg, 2.94 mmol) in DMA (10 mL) was stirred at 100 °C for 4 hrs. After cooling to r.t, the reaction was quenched with sat. NH 4Cl solution (15 mL), the resulting mixture was extracted with DCM (20 mL x 3). The combined organic phase was washed with brine (20 mL), dried over Na 2SO 4, filtered and concentrated in vacuum. The residue was purified by silica gel column (DCM : CH 3OH = 20: 1) to afford tert-butyl (S)-2-(methoxymethyl)-4-((R, E) -1 1, 2 6, 7-trimethyl-3-oxo-5 2, 5 3-dihydro-1 1H, 5 1H-11-oxa-4-aza-5 (2, 1) -benzo [d] imidazola-2 (2, 4) -pyridina-1 (4, 5) -pyrazolacycloundecaphane-5 6-yl) piperazine-1-carboxylate (380 mg, 61.6%). [M+H] + = 659.4. [1486]
  • 4
  • [ 1217728-72-7 ]
  • [ 3065098-72-5 ]
  • [ 3065098-73-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile at 75℃; Step 2: tert-butyl (S)-4-(3-((((1R,3S)-3-(hydroxymethyl)cyclopentyl)methyl)amino)-4-nitrophenyl)- 2-(methoxymethyl)piperazine-1-carboxylate To ((1S,3R)-3-(((5-fluoro-2-nitrophenyl)amino)methyl)cyclopentyl)methanol in acetonitrile was added TEA (1.0 g, 9.9 mmol, 1.5 equiv.) and tert-butyl (S)-2-(methoxymethyl)piperazine-1-carboxylate (1.27 g, 8.0 mmol, 1.2 equiv.) was then added. The mixture was heated to 75oC and stirred at 75oC for 24 hours. The reaction mixture was cooled to rt and diluted with DCM (10-15 vol) to dissolve the product. The mixture was washed with water (~2 x 10 vol). The organic layer was concentrated and purified by silica column chromatography (EA/DCM=0-30%) to afford tert-butyl (S)-4-(3-((((1R,3S)-3-(hydroxymethyl)cyclopentyl)methyl)amino)-4- nitrophenyl)-2-(methoxymethyl)piperazine-1-carboxylate. [M+H]+=479.3
  • 5
  • [ 1217728-72-7 ]
  • [ 3065098-74-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 24 h / 75 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C
  • 6
  • [ 1217728-72-7 ]
  • [ 3065098-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 24 h / 75 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C 3: hydrogen; platinum; Pt/V/C / tetrahydrofuran; water / 24 h / 40 °C / 3000.3 Torr
  • 7
  • [ 1217728-72-7 ]
  • [ 3065098-71-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 24 h / 75 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C 3: hydrogen; platinum; Pt/V/C / tetrahydrofuran; water / 24 h / 40 °C / 3000.3 Torr 4: methanol / 2 h / 20 °C
  • 8
  • [ 1217728-72-7 ]
  • [ 3067324-82-4 ]
  • [ 3067324-85-7 ]
YieldReaction ConditionsOperation in experiment
54.5% With RuPhos Pd G3; caesium carbonate; ruphos In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; 1.1 Step 1: (S)-4-(1-Chloro-3-(5-(difluoromethyl)-1,3,4-thiadiazol-2-yl)-6-(N-(3-methyloxetan-3-yl)-N-(2-(trimethylsilyl)ethoxy)methyl)sulfamoyl)imidazo[1,5-a]pyridin-8-yl)-2-(methoxymethyl)piperazine-1-carboxylic acid tert-butyl ester Under nitrogen, to a solution of 1,8-dichloro-3-(5-(difluoromethyl)-1,3,4-thiadiazol-2-yl)-N-(3-methyloxetan-3-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)imidazo[1,5-a]pyridine-6-sulfonamide (1 g, 1.67 mmol) and (S)-tert-butyl 2-(methoxymethyl)piperazine-1-carboxylate (576 mg, 2.50 mmol) in 1,4-dioxane (20 mL) were added cesium carbonate (1627 mg, 5.01 mmol), Ruphos (156 mg, 0.27 mmol), and Ruphos Pd G3 (139 mg, 0.17 mmol) in sequence.The reaction mixture was purged with nitrogen three times and stirred at 80°C under a nitrogen atmosphere for 2 hours.After the reaction was complete, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate.The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate, gradient: 0-30% ethyl acetate) to afford the title compound (yellow solid, 720 mg, 54.5% yield).
  • 9
  • [ 1217728-72-7 ]
  • [ 3067324-82-4 ]
  • [ 3067324-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ruphos; RuPhos Pd G3; caesium carbonate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Cooling with ice
 

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