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Chemical Structure| 4578-63-6 Chemical Structure| 4578-63-6

Structure of 4578-63-6

Chemical Structure| 4578-63-6

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Product Details of [ 4578-63-6 ]

CAS No. :4578-63-6
Formula : C11H14O3
M.W : 194.23
SMILES Code : CC(C)(C)C1=CC(O)=C(C=C1)C(O)=O
MDL No. :MFCD16999904
InChI Key :DEZCCOKUEFEDGQ-UHFFFAOYSA-N
Pubchem ID :433024

Safety of [ 4578-63-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 4578-63-6 ]

* 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 [ 4578-63-6 ]

[ 4578-63-6 ] Synthesis Path-Downstream   1~9

  • 2
  • [ 4578-63-6 ]
  • [ 100-39-0 ]
  • [ 173336-07-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; sodium iodide; In acetone; for 20h;Heating / reflux; A mixture of 5 g of <strong>[4578-63-6]2-hydroxy-4-tert-butyl-benzoic acid</strong>, 9.1 ml of benzyl bromide, 17 g of caesium carbonate, 0.3 g of sodium iodide and 500 ml of acetone is stirred for 20 hours under reflux and then filtered and the filtrate is concentrated by evaporation. The residue is partitioned between diethyl ether and water, the organic phases are concentrated by evaporation and the residue is purified by means of FC (1000 g of silica gel, dichloromethane/hexane=1 : 1). Title compound: Rf (DICHLOROMETHANE/HEXANE=1 1) =0.47.
  • 3
  • [ 4578-63-6 ]
  • [ 100-39-0 ]
  • [ 534-17-8 ]
  • [ 173336-07-7 ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; In acetone; n) 2-Benzyloxy-4-tert-butyl-benzoic acid benzyl ester A mixture of 5 g of <strong>[4578-63-6]2-hydroxy-4-tert-butyl-benzoic acid</strong>, 9.1 ml of benzyl bromide, 17 g of caesium carbonate, 0.3 g of sodium iodide and 500 ml of acetone is stirred for 20 hours under reflux and then filtered and the filtrate is concentrated by evaporation. The residue is partitioned between diethyl ether and water, the organic phases are concentrated by evaporation and the residue is purified by means of FC (1000 g of silica gel, dichloromethane/hexane=1:1). Title compound: Rf (dichloromethane/hexane=1:1)=0.47.
  • 4
  • [ 932114-04-0 ]
  • [ 4578-63-6 ]
  • 4-({5-[([4-(1,1-dimethylethyl)-2-hydroxyphenyl]carbonyl}amino)methyl]-1,6-diethyl-1H-pyrazolo[3,4-b]pyridin-4-yl}amino)-1-piperidinecarboxamide formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; Example 302 4-({5-[([4-(1 ,1 -dimethylethyl)-2-hydroxyphenyl]carbonyl}amino)- methyl]-1,6-diethyl-1 H-pyrazolo[3,4-b]pyridin-4-yl}amino)-1-piperidine- carboxamide formate EPO <DP n="210"/>, formateA solution of Intermediate 26 (20mg) in DMF (1ml) was added to 4-(1 ,1-dimethylethyl)-2- hydroxybenzoic acid (13.6mg) followed by a solution of PyBOP (36mg) in DMF (0.3ml) and DIPEA (0.025ml). The mixture was allowed to stand at room temperature for 18h and was then evaporated to dryness in vacuo. The residue was taken up in dichloromethane, washed with water and purified by mass directed autoprep HPLC to give Example 302 as a solid (11.8mg). LCMS showed MH+ = 522; TRET = 2.71 min.
  • 5
  • [ 4578-63-6 ]
  • [ 216967-68-9 ]
YieldReaction ConditionsOperation in experiment
prepared from <strong>[4578-63-6]4-tert-butyl-2-hydroxy-benzoic acid</strong>
  • 6
  • [ 932114-04-0 ]
  • [ 4578-63-6 ]
  • [ 932113-35-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; A solution of Intermediate 26 (20 mg) in DMF (1 ml) was added to <strong>[4578-63-6]4-(1,1-dimethylethyl)-2-hydroxybenzoic acid</strong> (13.6 mg) followed by a solution of PyBOP (36 mg) in DMF (0.3 ml) and DIPEA (0.025 ml). The mixture was allowed to stand at room temperature for 18 h and was then evaporated to dryness in vacuo. The residue was taken up in dichloromethane, washed with water and purified by mass directed autoprep HPLC to give Example 302 as a solid (11.8 mg). LCMS showed MH+=522; TRET=2.71 min.
  • 7
  • [ 66232-34-6 ]
  • [ 4578-63-6 ]
  • 8
  • [ 124-38-9 ]
  • [ 585-34-2 ]
  • [ 4578-63-6 ]
  • 9
  • 3-methyl-1,4'-bipiperidine [ No CAS ]
  • [ 4578-63-6 ]
  • (2-hydroxy-4-tert-butylphenyl)(3-methyl-1,4'-bipiperidin-1'-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% Example 12 (2-Hydroxy-4-tert-butylphenyl)(3-methyl-1,4'-bipiperidin-1'-yl)methanone 100 mg (0.52 mmol) of <strong>[4578-63-6](2-hydroxy-4-tert-butyl)benzoic acid</strong> were dissolved in 2.7 ml of DMF, and 99 mg (0.52 mmol) of EDC, 79 mg (0.52 mmol) of HOBT and 266 mg (2.1 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred at RT for 10 min. 94 mg (0.52 mmol) of 3-methyl-1,4'-bipiperidine were then added, and the mixture was subsequently stirred at RT overnight. The resulting product was separated by preparative HPLC [Reprosil, C18 10 mum, 250 mm*30 mm, acetonitrile/water 10:90 to 90:10 over a run time of 38 min]. After HPLC control, the product-containing fractions were combined and concentrated. The residue was dried under HV. This gave 35 mg (19% of theory) of the title compound.10893] LC-MS [Method 1]: R=0.85 mm; MS (ESIpos):mlz=359 (M+H)j0894] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=0.71-0. 91 (m, 1H), 0.82 (d, 3H), 1.24 (s, 9H), 1.3-1.8 (m, 8H),1.98-2.09 (m, 1H), 2.30-2.46 (m, 2H), 2.64-2.78 (m, 5H),2.9-2.96 (m, 1H), 6.82-6.87 (m, 2H), 6.99-7.04 (m, 2H)
 

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