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Chemical Structure| 1104383-06-3 Chemical Structure| 1104383-06-3

Structure of 1104383-06-3

Chemical Structure| 1104383-06-3

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Product Details of [ 1104383-06-3 ]

CAS No. :1104383-06-3
Formula : C11H20N2O3
M.W : 228.29
SMILES Code : O=C(OC(C)(C)C)N1C(C)(C(NCC1)=O)C
MDL No. :MFCD18845275
InChI Key :ADXBXIQTAQOYRW-UHFFFAOYSA-N
Pubchem ID :57657568

Safety of [ 1104383-06-3 ]

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 [ 1104383-06-3 ]

* 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 [ 1104383-06-3 ]

[ 1104383-06-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1104383-06-3 ]
  • [ 4522-35-4 ]
  • [ 824-94-2 ]
  • tert-butyl 4-[2-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxopiperazine-1-carboxylate [ No CAS ]
  • tert-butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxopiperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1-(chloromethyl)-4-methoxy-benzene (2.10 mL, 15.5 mmol) was added to a stirred mixture of <strong>[4522-35-4]3-iodo-1H-pyrazole</strong> (2.01 g, 10.4 mmol) and Cs2CO3 (6.70 g, 20.6 mmol) in DMF (30.0 mL). The reaction mixture was stirred at 60 C for 2 hours and then, cooled to room temperature. Water (100mL) was added and aqueous was extracted with EtOAc (3 x 50 mL). Combined organic extracts were washed with aqueous saturated NH4Cl (25 mL) solution, brine (25 mL) and dried over MgSO4. The mixture was filtered and concentrated to afford 4.06 g of crude material. The residue was adsorbed on silica using DCM and purified by silica gel chromatography to afford 3-iodo-1-[(4- methoxyphenyl)methyl]pyrazole and 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole (3.18 g, 98%) as a white solid as a ca.5:1 mixture of regioisomers. Major Regioisomer: 1H NMR (400 MHz, CDCl3) 7.23 - 7.15 (m, 3H), 7.12 (d, J = 2.3 Hz, 1H), 6.92 - 6.85 (m, 2H), 6.40 (d, J = 2.3 Hz, 1H), 5.24 (s, 2H). : ESI-MS m/z calc.313.9916, found 314.98 (M+1)+; Retention time: 0.93 minutes Using Method J A mixture of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (915 mg, 4.01 mmol), regioisomers mix of 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole/3- iodo-1-[(4-methoxyphenyl)methyl]pyrazole (1.51 g, 4.81 mmol), iodocopper (381.7 mg, 2.00 mmol), N,N'-dimethylethane-1,2-diamine (353.3 mg, 426.7 muL, 4.01 mmol) and K3PO4 (1.702 g, 8.02 mmol) in DMF (18.3 mL) was heated at 120 C for 3.5 hours. The reaction mixture was cooled to r.t. and filtered to remove the copper salts. The filtrate was diluted with water and aqueous was extracted twice with ethyl acetate. Organic extracts were washed with water, followed with brine, dried over Na2SO4, filtered and (0666) concentrated under reduced pressure. The recovered crude compound was purified by silica gel chromatography to give a mixture of the tert-butyl 4-[2-[(4- methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1-carboxylate and the tert-butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo- piperazine-1-carboxylate (1.603 g, 96%). Major regioisomer: 1H NMR (400 MHz, DMSO-d6) 7.70 (d, J = 2.3 Hz, 1H), 7.22 - 7.11 (m, 2H), 6.91 - 6.81 (m, 2H), 6.61 (d, J = 2.3 Hz, 1H), 5.14 (s, 2H), 3.86 - 3.79 (m, 2H), 3.69 (s, 3H), 3.66 - 3.58 (m, 2H), 1.58 (s, 6H), 1.40 (s, 9H). ESI-MS m/z calc.414.2267, found 416.38 (M+1)+
  • 2
  • [ 1104383-06-3 ]
  • [ 4522-35-4 ]
  • [ 824-94-2 ]
  • 1-[2-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-3,3-dimethylpiperazin-2-one hydrochloride [ No CAS ]
  • 1-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-3,3-dimethylpiperazin-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
1-(chloromethyl)-4-methoxy-benzene (2.10 mL, 15.5 mmol) was added to a stirred mixture of <strong>[4522-35-4]3-iodo-1H-pyrazole</strong> (2.01 g, 10.4 mmol) and Cs2CO3 (6.70 g, 20.6 mmol) in DMF (30.0 mL). The reaction mixture was stirred at 60 C for 2 hours and then, cooled to room temperature. Water (100mL) was added and aqueous was extracted with EtOAc (3 x 50 mL). Combined organic extracts were washed with aqueous saturated NH4Cl (25 mL) solution, brine (25 mL) and dried over MgSO4. The mixture was filtered and concentrated to afford 4.06 g of crude material. The residue was adsorbed on silica using DCM and purified by silica gel chromatography to afford 3-iodo-1-[(4- methoxyphenyl)methyl]pyrazole and 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole (3.18 g, 98%) as a white solid as a ca.5:1 mixture of regioisomers. Major Regioisomer: 1H NMR (400 MHz, CDCl3) 7.23 - 7.15 (m, 3H), 7.12 (d, J = 2.3 Hz, 1H), 6.92 - 6.85 (m, 2H), 6.40 (d, J = 2.3 Hz, 1H), 5.24 (s, 2H). : ESI-MS m/z calc.313.9916, found 314.98 (M+1)+; Retention time: 0.93 minutes Using Method J A mixture of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (915 mg, 4.01 mmol), regioisomers mix of 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole/3- iodo-1-[(4-methoxyphenyl)methyl]pyrazole (1.51 g, 4.81 mmol), iodocopper (381.7 mg, 2.00 mmol), N,N'-dimethylethane-1,2-diamine (353.3 mg, 426.7 muL, 4.01 mmol) and K3PO4 (1.702 g, 8.02 mmol) in DMF (18.3 mL) was heated at 120 C for 3.5 hours. The reaction mixture was cooled to r.t. and filtered to remove the copper salts. The filtrate was diluted with water and aqueous was extracted twice with ethyl acetate. Organic extracts were washed with water, followed with brine, dried over Na2SO4, filtered and (0666) concentrated under reduced pressure. The recovered crude compound was purified by silica gel chromatography to give a mixture of the tert-butyl 4-[2-[(4- methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1-carboxylate and the tert-butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo- piperazine-1-carboxylate (1.603 g, 96%). Major regioisomer: 1H NMR (400 MHz, DMSO-d6) 7.70 (d, J = 2.3 Hz, 1H), 7.22 - 7.11 (m, 2H), 6.91 - 6.81 (m, 2H), 6.61 (d, J = 2.3 Hz, 1H), 5.14 (s, 2H), 3.86 - 3.79 (m, 2H), 3.69 (s, 3H), 3.66 - 3.58 (m, 2H), 1.58 (s, 6H), 1.40 (s, 9H). ESI-MS m/z calc.414.2267, found 416.38 (M+1)+ A HCl solution in dioxane (4.84 mL of 4 M, 19.3 mmol) was added to a stirred solution of the mixture of regioisomers tert-butyl 4-[2-[(4- methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1-carboxylate/ tert- butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1- carboxylate (1.60 g, 3.87 mmol) in DCM (16 mL). The reaction mixture was stirred 24h at room temperature and then, solvents were removed by evaporation in vacuo. The recovered gummy residue was dissolved in DCM and sonicated. Diethyl ether was added dropwise until full precipitation of the desired product in the sonicator bath. The mixture was filtered. The recovered white solid was washed with diethyl ether and dried under vacuum to give a mixture of regioisomers 1-[2-[(4-methoxyphenyl)methyl]pyrazol-3-yl]- 3,3-dimethyl-piperazin-2-one and 1-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-3,3- dimethyl-piperazin-2-one (1.153 g, 85%) as hydrochloride salt. Major isomer: 1H NMR (400 MHz, DMSO-d6) 10.07 (broad s, 1H), 7.79 (d, J = 2.3 Hz, 1H), 7.23 - 7.08 (m, 2H), 6.93 - 6.83 (m, 2H), 6.64 (d, J = 2.3 Hz, 1H), 5.18 (s, 2H), 4.04 (t, J = 5.8 Hz, 2H), 3.71 (s, 3H), 3.65 - 3.50 (m, 2H), 3.42 - 3.32 (m, 1H), 1.58 (s, 6H). ESI-MS m/z calc. 314.1743, found 315.78 (M+1)+; Retention time: 0.34 using Method J
 

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