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Chemical Structure| 1097180-24-9 Chemical Structure| 1097180-24-9

Structure of 1097180-24-9

Chemical Structure| 1097180-24-9

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Product Details of [ 1097180-24-9 ]

CAS No. :1097180-24-9
Formula : C13H22BrNO3
M.W : 320.22
SMILES Code : O=C(N1[C@H](CC(CBr)=O)CCCC1)OC(C)(C)C

Safety of [ 1097180-24-9 ]

Application In Synthesis of [ 1097180-24-9 ]

* 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 [ 1097180-24-9 ]

[ 1097180-24-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1097180-24-9 ]
  • [ 42182-27-4 ]
  • [ 1097264-60-2 ]
  • C19H24N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 2.5h; To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.27 mmol) in DMF (1 ml), 2-amino-4-pyridinecarbonitrile (0.032 g, 0.27 mmol) was added and the mixture heated at 80° C. for 2.5 h. The reaction was eluted through a SCX column. Collected fractions gave 0.049 g of an oil containing a mixture of the final compound, the corresponding N-Boc protected derivative and some residual 2-amino-4-pyridinecarbonitrile. [N-Boc derivative data: HPLC: rt=0.65 min, peak observed: 341 (M+1). C19H24N4O2 requires 340]. The crude was dissolved in DCM (2.50 ml) and the resulting solution cooled to 0° C. TFA (0.50 ml) was added dropwise, the reaction left under stirring for 1 h and then eluted through a SCX column. Collected fractions gave the title compound D15 (0.041 g, 0.17 mmol, 63percent yield from D2, two steps) contaminated with some residual 2-amino-4-pyridinecarbonitrile.UPLC: rt=0.38 min, peak observed: 241 (M+1). C14H16N4 requires 240.
  • 2
  • [ 1097180-24-9 ]
  • [ 1597-32-6 ]
  • [ 1097264-67-9 ]
  • C18H24FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 2.5h; To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.11 g, 0.26 mmol) in DMF (1 ml) was added <strong>[1597-32-6]6-fluoro-2-pyridinamine</strong> (0.029 g, 0.26 mmol) and the mixture was stirred at 80 C. for 2.5 h. The reaction mixture was eluted through a SCX column. Collected fractions gave 0.032 g of an oil containing a mixture of the title compound, the corresponding N-Boc protected derivative and some residual <strong>[1597-32-6]6-fluoro-2-pyridinamine</strong>. [N-Boc derivative data. LC-MS: rt=1.54 min, peak observed: 334 (M+1). C18H24FN3O2 requires 333]. The crude was dissolved in DCM (2.50 ml) and the resulting solution cooled to 0 C. TFA (0.50 ml) was added dropwise, the reaction left under stirring for 1 h and then eluted through a SCX column. Collected fractions gave the title compound D22 (0.020 g) contaminated with <strong>[1597-32-6]6-fluoro-2-pyridinamine</strong>. The material was used without further purification in the next step.HPLC (walk-up): rt=1.50 min. MS: (ES/+) m/z: 234 (M+1). C13H16FN3 requires 233.
  • 3
  • [ 1097264-90-8 ]
  • [ 1097180-24-9 ]
  • [ 1097264-91-9 ]
  • C19H26FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 2h; To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.19 g, 0.60 mmol) in DMF (1 ml), <strong>[1097264-90-8]5-fluoro-3-(methyloxy)-2-pyridinamine</strong> D48 (0.071 g, 0.50 mmol) was added and the mixture stirred at 80 C. for 2 h. The reaction mixture was eluted through a SCX column. Collected fractions gave 0.14 g of a crude oil containing a mixture of the title compound, the corresponding N-Boc protected derivative and some residual <strong>[1097264-90-8]5-fluoro-3-(methyloxy)-2-pyridinamine</strong>. The material was used in the next step without further purification. [N-Boc derivative data. MS: (ES/+) m/z: 364 (M+1). C19H26FN3O3 requires 363]. The crude (0.14 g) was dissolved in DCM (2 ml) and TFA (0.40 ml) was added at 0 C. The reaction was left under stirring for 1 h, then volatiles were removed under vacuum and the residue eluted through a SCX column. Collected fractions gave an oil (0.13 g) containing the title compound D49. The material was used in the next step without further purification. UPLC: rt=0.33 min, peak observed: 264 (M+1). C14H18FN3O requires 263.
  • 4
  • [ 54568-12-6 ]
  • [ 1097180-24-9 ]
  • [ 1097180-31-8 ]
  • C19H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 4h; A solution of 1,1-dimethylethyl (25)-2-(3-bromo-2-oxopropyl)-l-piperidinecarboxylate D2 (0.10 g, 0.31 mmol) and 5,6-dimethyl-4-pyrimidinamine D9 (0.042 g, 0.34 mmol) in DMF (1 ml) was stirred at 80 0C for 4 h. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (from DCM 100 to DCM /MeOH 98/2) and then eluted through a SCX column to afford a crude material (0.018 g) containing the title compound DlO, the corresponding N-Boc protected derivative and some residual 5,6-dimethyl-4-pyrimidinamine. [N-Boc derivative data. UPLC: rt = 0.58 min, peak observed: 345 (M+l). C1QH2SN4O2 requires 344]. The crude was dissolved in DCM (2 ml), TFA (0.50 ml) was added drop wise and the reaction left under stirring for 1 h at room temperature. Volatiles were removed under reduced pressure and the residue eluted through a SCX cartridge to afford a crude material containing the title compound DlO (0.012 g) contaminated with some residual 5,6-dimethyl-4-pyrimidinamine. UPLC: rt = 0.36 min, peak observed: 245 (M+l). C14H20N4 requires 244.
 

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