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Product Details of [ 120800-50-2 ]

CAS No. :120800-50-2 MDL No. :MFCD03791231
Formula : C11H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QLPWWMSKVYYSEY-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :2794761
Synonyms :

Safety of [ 120800-50-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120800-50-2 ]

* 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 [ 120800-50-2 ]

[ 120800-50-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 79-37-8 ]
  • [ 890315-80-7 ]
  • [ 120800-50-2 ]
  • [ 890314-86-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; citric acid In hexane; dichloromethane; di-isopropyl ether; ethyl acetate; N,N-dimethyl-formamide 497 Example 497 Example 497 1.5 mL of methylene chloride, 0.010 mL of N,N-dimethylformamide and 0.062 mL of oxalyl chloride were added sequentially to 0.13 g of 6-(piperidin-1-yl)pyridine-3-carboxylic acid at room temperature and stirred at the same temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, 1.5 mL of methylene chloride was added and, while ice-cooled, the mixture was added to a mixed solution of 1.5 mL of methylene chloride and 0.14 mL of triethylamine containing 0.15 g of tert-butyl 2-amino-4-phenethylbenzoate and stirred at room temperature overnight. The solvent was evaporated under reduced pressure and ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.17 g of tert-butyl 4-phenethyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate as white solid. 1H-NMR (CDCl3) δ: 1.52-1.77 (6H, m), 1.61 (9H, s), 2.97 (4H, s), 3.66-3.73 (4H, m), 6.70 (1H, d, J = 9.2 Hz), 6.84 (1H, dd, J = 8.2, 1.7 Hz), 7.17-7.31 (5H, m), 7.90 (1H, d, J = 8.2 Hz), 8.10 (1H, dd, J = 9.2, 2.7 Hz), 8.86 (1H, d, J = 1.7 Hz), 8.89 (1H, d, J = 2.7 Hz), 12. 11 (1H, s).
  • 2
  • [ 79-37-8 ]
  • [ 890315-92-1 ]
  • [ 120800-50-2 ]
  • [ 890316-43-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane; N,N-dimethyl-formamide 320 Example 320 Example 320 1.3 mL of methylene chloride, 1.3 μL of N,N-dimethylformamide and 0.031 mL of oxalyl chloride were added sequentially to 69 mg of 6-(piperidin-1-yl)pyridine-3-carboxylic acid at room temperature, and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 57 mg of tert-butyl 2-amino-4-phenoxybenzoate, 3.7 mL of methylene chloride and 0.22 mL of triethylamine and stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane: ethyl acetate = 8:1] to obtain tert-butyl 4-phenoxy-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate.
  • 3
  • [ 79-37-8 ]
  • [ 120800-50-2 ]
  • [ 890316-40-2 ]
  • [ 890316-46-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane; N,N-dimethyl-formamide 368 Example 368 Example 368 1.3 mL of methylene chloride, 1.3 μL of N,N-dimethylformamide and 0.031 mL of oxalyl chloride were sequentially added to 69 mg of 6-(piperidin-1-yl)pyridine-3-carboxylic acid at room temperature, and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 54 mg of tert-butyl 2-amino-4-phenylbenzoate, 3.7 mL of methylene chloride and 0.22 mL of triethylamine and stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane: ethyl acetate = 4:1] to obtain tert-butyl 4-phenyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate.
  • 4
  • [ 120800-50-2 ]
  • [ 1031337-88-8 ]
  • [ 1054611-43-6 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane
  • 5
  • [ 120800-50-2 ]
  • [ 1201663-76-4 ]
  • [ 1201662-24-9 ]
YieldReaction ConditionsOperation in experiment
60% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 185 S^-Dichloro-N-^'-fluorobiphenyM-yOmethyO-Z-hydroxy-N^-((isobutyl amino)methyl)benzyl)benzene sulfonamide (Compound E of Example 184, 0.04 g, 0.066 mmol, 1 eq) was dissolved in acetonitrile. DlPEA (0.034 mL, 0.198 mmol, 3 eq) was added followed by 6-(piperidin-I-yl) nicotinic acid (0.013 g, 0.066 mmol, 1 eq), EDCI (0.018 g, 0.099 mmol, 1.5 eq) and HOBT (0.013 g, 0.099 mmol, 1.5 eq). The reaction mixture was stirred at ambient temperature for 12 h and concentrated to remove the volatiles. The residue obtained was dissolved in ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (0.03 g, 60%). 1H NMR (400 MHz, OMSO-d6) δ 0.74 (t, 6H), 1.50-1.59 (m, 6H), 1.9-2.0 (s, 1H), 3.03-3.04 (t, 2H), 3.54-3.55 (t, 4H), 4.45-4.49 (m, 6H), 6.82-6.84 (d, 1H), 6.9 (t, 1H), 7.03-7.05 (m, 2H), 7.14-7.28 (m, 6H), 7.42- 7.44 (d, 2H), 7.53-7.61 (m, 4H), 7.80 (s, 1H), 8.12 (s, 1H). MS (ESI): 788.6 (M - H)'.
  • 8
  • [ 120800-50-2 ]
  • 4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(pyrrolidin-1-ylmethyl)benzoate [ No CAS ]
  • 5,6-dihydroxy-4-oxo-2-(4-((4-(pyrrolidin-1-ylmethyl)benzoyl)oxy)phenyl)-4H-chromen-7-yl 6-(piperidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.4% With dmap; dicyclohexyl-carbodiimide In dichloromethane; dimethyl sulfoxide at 20℃; Preparation of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein(7a-7f) General procedure: A 50 mL, three-necked, round-bottomed flask, fitted witha nitrogen inlet adapter, was charged with 4′-N-substituted(aminomethyl) benzoate derivative of scutellarein (5a-d)(0.21 mmol), 6-substituted nicotinic acid (6a-c) (0.27mmol), 4-dimethylaminopyridine (0.21 mmol), CH2Cl2 (25 mL), and dimethyl sulphoxide (DMSO) (1 mL). Theresulting mixture was stirred for 30 min until it becomehomogeneous and a solution of dicyclohexylcarbodiimide(0.21 mmol) in CH2Cl2 (5.0 mL) was then added slowly tothe solution. After stirring at room temperature for 24 h, themixture was filtered and concentrated in vacuo. The residuewas purified by flash column chromatography on silica gelusing gradient elution with chloroform/methanol (100:1 to30:1, v/v) to give the target compound. Products 7a-f wereobtained in this way as yellow solids in 36.4-45.1% yield. 5,6-dihydroxy-4-oxo-2-(4-((4-(pyrrolidin-1-ylmethyl)benzoyl)oxy)phenyl)-4H-chromen-7-yl 6-(piperidin-1-yl)nicotinate (7a)Yellow solid, yield: 36.4 %, m.p. 242-244 °C.1H NMR(400 MHz, DMSO-d6): δ = 12.95 (brs, 1H, 5-OH), 8.74(s,1H, pyr-H2), 8.18(d, J = 8.0 Hz, 2H, Ar″-H2,6), 8.08 (d, J= 8.0 Hz, 2H, Ar′-H2,6), 8.02 (dd, J1 = 8.0 Hz, J2 = 2.4 Hz,1H, pyr-H4), 7.50-7.46 (m, 2H, Ar″-H3,5), 7.28-7.20 (m,2H, Ar′-H3,5), 7.03 (s, 1H, Ar-H3), 6.69 (s, 1H, Ar-H8),6.52(d, J = 8.0 Hz, 1H, pyr-H5), 3.55-3.44 (m, 6H, 3 ×CH2N), 2.46-2.41(m, 4H, 2 × CH2N), 1.99-1.93 (m, 10H,5 × CH2). 13C NMR (100 MHz, DMSO-d6) δ = 182.7 (C,C-4), 164.6 (C, C-7′), 163.7 (C, C-2), 163.3 (C, pyr-CO),159.1 (C, C-6), 157.8(C, C-5), 154.5 (C, C-9), 153.9 (CH,pyr-C2), 153.0 (C, C-4′), 152.2 (C, C-7), 145.8(C, C-4′′),138.4 (CH, pyr-C4), 130.4 (2 × CH, C-2′′, C-6′′), 129.7(2 × CH, C-2′, C-6′), 129.4 (2 × CH, C-3′′, C-5′′), 128.7(2 × CH, C-3′, C-5′), 127.5 (C, pyr-C3), 123.3 (C, C-10),123.1 (CH, pyr-C5), 111.7 (CH, C-3), 106.5 (CH, C-8),63.4 (CH2, CH2N), 53.0 (2 × CH2, 2×CH2N), 47.2 (2 ×CH2, 2×CH2N), 25.7 (2 × CH2, 2×CH2CH2N), 25.3 (2 ×CH2, 2×CH2CH2N), 24.1 (CH2, CH2CH2CH2). ESI-MS(m/z): 662.3[M+H]+. HRESIMS m/z (pos): 662.2489C38H36N3O8 (calcd. 662.2497).
  • 9
  • [ 120800-50-2 ]
  • 4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(piperidin-1-ylmethyl)benzoate [ No CAS ]
  • 5,6-dihydroxy-4-oxo-2-(4-((4-(piperidin-1-ylmethyl)benzoyl)oxy)phenyl)-4H-chromen-7-yl 6-(piperidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.4% With dmap; dicyclohexyl-carbodiimide In dichloromethane; dimethyl sulfoxide at 20℃; Preparation of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein(7a-7f) General procedure: A 50 mL, three-necked, round-bottomed flask, fitted witha nitrogen inlet adapter, was charged with 4′-N-substituted(aminomethyl) benzoate derivative of scutellarein (5a-d)(0.21 mmol), 6-substituted nicotinic acid (6a-c) (0.27mmol), 4-dimethylaminopyridine (0.21 mmol), CH2Cl2 (25 mL), and dimethyl sulphoxide (DMSO) (1 mL). Theresulting mixture was stirred for 30 min until it becomehomogeneous and a solution of dicyclohexylcarbodiimide(0.21 mmol) in CH2Cl2 (5.0 mL) was then added slowly tothe solution. After stirring at room temperature for 24 h, themixture was filtered and concentrated in vacuo. The residuewas purified by flash column chromatography on silica gelusing gradient elution with chloroform/methanol (100:1 to30:1, v/v) to give the target compound. Products 7a-f wereobtained in this way as yellow solids in 36.4-45.1% yield.
  • 10
  • [ 120800-50-2 ]
  • 4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(morpholinomethyl)benzoate [ No CAS ]
  • 5,6-dihydroxy-2-(4-((4-(morpholinomethyl)benzoyl)oxy)phenyl)-4-oxo-4H-chromen-7-yl 6-(piperidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.6% With dmap; dicyclohexyl-carbodiimide In dichloromethane; dimethyl sulfoxide at 20℃; Preparation of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein(7a-7f) General procedure: A 50 mL, three-necked, round-bottomed flask, fitted witha nitrogen inlet adapter, was charged with 4′-N-substituted(aminomethyl) benzoate derivative of scutellarein (5a-d)(0.21 mmol), 6-substituted nicotinic acid (6a-c) (0.27mmol), 4-dimethylaminopyridine (0.21 mmol), CH2Cl2 (25 mL), and dimethyl sulphoxide (DMSO) (1 mL). Theresulting mixture was stirred for 30 min until it becomehomogeneous and a solution of dicyclohexylcarbodiimide(0.21 mmol) in CH2Cl2 (5.0 mL) was then added slowly tothe solution. After stirring at room temperature for 24 h, themixture was filtered and concentrated in vacuo. The residuewas purified by flash column chromatography on silica gelusing gradient elution with chloroform/methanol (100:1 to30:1, v/v) to give the target compound. Products 7a-f wereobtained in this way as yellow solids in 36.4-45.1% yield.
  • 11
  • [ 120800-50-2 ]
  • C34H30N2O7 [ No CAS ]
  • 2-(4-((4-((4-benzylpiperazin-1-yl)methyl)benzoyl)oxy)phenyl)-5,6-dihydroxy-4-oxo-4H-chromen-7-yl 6-(piperidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.2% With dmap; dicyclohexyl-carbodiimide In dichloromethane; dimethyl sulfoxide at 20℃; Preparation of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein(7a-7f) General procedure: A 50 mL, three-necked, round-bottomed flask, fitted witha nitrogen inlet adapter, was charged with 4′-N-substituted(aminomethyl) benzoate derivative of scutellarein (5a-d)(0.21 mmol), 6-substituted nicotinic acid (6a-c) (0.27mmol), 4-dimethylaminopyridine (0.21 mmol), CH2Cl2 (25 mL), and dimethyl sulphoxide (DMSO) (1 mL). Theresulting mixture was stirred for 30 min until it becomehomogeneous and a solution of dicyclohexylcarbodiimide(0.21 mmol) in CH2Cl2 (5.0 mL) was then added slowly tothe solution. After stirring at room temperature for 24 h, themixture was filtered and concentrated in vacuo. The residuewas purified by flash column chromatography on silica gelusing gradient elution with chloroform/methanol (100:1 to30:1, v/v) to give the target compound. Products 7a-f wereobtained in this way as yellow solids in 36.4-45.1% yield.
  • 12
  • [ 110-89-4 ]
  • [ 5326-23-8 ]
  • [ 120800-50-2 ]
YieldReaction ConditionsOperation in experiment
at 120 - 130℃; Inert atmosphere; General procedure: The synthetic route is outlined in Scheme 1A 100 mL, three-necked, round-bottomed flask, fittedwith a nitrogen inlet adapter, was charged with6-chloronicotinic acid (500.0 mg, 3.18 mmol) and substitutedamine (15.92 mmol). The resulting mixture wasstirred for 30 min until it became homogeneous and thenstirred at 120-130 °C for 6 h, when thin layer chromatography(TLC) (eluent:dichloromethane/methanol/acetic acid(15:1:1, v/v/v)) indicated that the reaction was complete.The resulting mixture was partially purified by flash columnchromatography on silica gel, using dichloromethane/methanol/acetic acid (30:1:1, v/v/v) as the eluent. Theresulting crude product was dissolved in ethanol (10 mL)and precipitated by the addition of acetic acid (0.5 mL).This process was repeated three times and the suspensionwas then centrifuged for 10 min at 4000 g. The sedimentwas collected and washed with Et2O to obtain pure 6-substituted nicotinic acid (6a-6c).
  • 13
  • [ 15317-58-5 ]
  • [ 120800-50-2 ]
  • 2-(1H-indol-3-yl)-5-(6-(piperidin-1-yl)-pyridin-3-yl)-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With trichlorophosphate at 50℃;
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