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[ CAS No. 1246372-53-1 ] {[proInfo.proName]}

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Chemical Structure| 1246372-53-1
Chemical Structure| 1246372-53-1
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Product Details of [ 1246372-53-1 ]

CAS No. :1246372-53-1 MDL No. :MFCD16618965
Formula : C23H36BNO6 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 433.35 Pubchem ID :-
Synonyms :

Safety of [ 1246372-53-1 ]

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

Application In Synthesis of [ 1246372-53-1 ]

* 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 [ 1246372-53-1 ]

[ 1246372-53-1 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 269410-22-2 ]
  • [ 109384-19-2 ]
  • [ 1246372-53-1 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; I Intermediate I; 4-[2-Methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]- piperidine-1-carboxylic acid tert-butyl esterTo a solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenol (0.8 g, 3.2 mmol, 1 eq), 1-boc-4-hydroxypiperidine (0.97 g, 4.8 mmol, 1.5 eq) and triphenylphosphine (1.26 g, 4.8 mmol, 1.5 eq) in anhydrous THF (8 mL) was added DIAD (0.94 mL, 4.8 mmol, 1.5 eq) dropwise at OºC. The solution was stirred at RT for 45 h. The solvent was removed, and the resulting light orange oily residue was treated with 20% AcOEt/c-hexane to give white crystals (PPh3O) which were filtered off and washed with the same mixture. The filtrate was evaporated to give an oily residue which was treated with c-hexane and a few drops of AcOEt to give a white precipitate that was removed by filtration and an oily residue that solidified upon standing. The crude product (1.93 g containing some c-hexane) was used as it was in the subsequent step. The remainder was purified by column chromatography (Isolute Flash Si Il column, 25 g silica gel, 0- 8% AcOEt in c-hexane) to give the pure desired product (0.991 g). HPLC-MS (10- 95% B in 4 min at 0.5 mL + 2 min 100% B, flow 0.8 ml_/min, 5OºC): tR= 5.10 min, [M+H]+ m/z 334.3.
9.1 g With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; 1 Intermediate 16: Tert-butyl 4-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenoxy)piperidine-1-carboxylate To a 500 ml round bottom flask were added under an argon atmosphere 2-methoxy-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (6 g, 23.99 mmol), tert-butyl 4- hydroxypiperidine-1-carboxylate (5.5 g, 26.80 mmol), PPh3 (7 g, 26.70 mmol) and THF (120 ml). DIAD (5.6 ml, 28.80 mmol) was slowly added and the RM was stirred at RT overnight. The mixture was diluted with EtOAc and an aq. sat. solution of NaHCO3 was added. The organic phase was washed with brine, dried over MgSO4 and the residue was purified by chromatography on silica gel eluting with EtOAc (from 0 % to 20 %) in CHX, yielding the title compound as a solid (9.1 g). Method D: Rt = 1.41 min; [M+H]+= 434.
  • 2
  • [ 1246372-52-0 ]
  • [ 1246372-53-1 ]
  • [ 1246372-54-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In 1,4-dioxane; water at 115℃; J Intermediate J; 4-[4-(5-lodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-2-methoxy-phenoxy]- piperidine-1-carboxylic acid tert-butyl esterTo a suspension of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.262 g,0.794 mmol, 1 eq) in 1 ,4-dioxane (13 mL), 4-[2-Methoxy-4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (0.413 g, 0.953 mmol, 1.2 eq), Cs2CO3 (0.517 g, 1.588 mmol, 2 eq), dichlorobis(triphenylphosphine)palladium(ll) (0.056 g, 0.079 mmol, 0.1 eq) and water (6 ml) were added. The resulting mixture was heated at 115ºC overnight. Solvents were removed and the crude was purified in an lsolute Flash Si Il column (25 g silica gel, 10%-21% EtOAc in c-hexane) to give the desired product (0.21 g). HPLC-MS (10-95% B in 4 min at 0.5 mL + 2 min 100% B1 flow 0.8 mL/min, 5OºC): tR= 4.98 min, [M+H]+ m/z 557.1.
  • 3
  • [ 1246372-53-1 ]
  • 4-bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one [ No CAS ]
  • tert-butyl 4-(2-methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)phenoxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.4 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 100℃; for 2.5h; Inert atmosphere; 1.1 Step 1: tert-butyl 4-(2-methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4- yl)phenoxy)piperidine-1-carboxylate To a 250 ml round bottom flask were added under an argon atmosphere 4-bromo-2- methyl-2,7-naphthyridin-1(2H)-one (intermediate 5, 2.3 g, 7.02 mmol), tert-butyl 4-(2- methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidine-1-carboxylate (intermediate 16, 3.5 g, 8.08 mmol), K2CO3 (3.0 g, 21.71 mmol), ACN (40 ml) and water (10 ml). Solid PdCl2(dppf) (500 mg, 0.683 mmol) was added and the RM was stirred at 100 °C for 2.5 h. The mixture was cooled to RT, filtered through CELITE, the filtrate was diluted with Et2O and the resulting mixture was filtered, yielding the title compound as a solid (3.4 g). Method D: Rt = 1.06 min; [M+H]+= 466.
  • 4
  • [ 1246372-53-1 ]
  • 1-(2-Methoxy-5-(4-((4-(2-methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)phenoxy)piperidin-1-yl)methyl)piperidine-1-carbonyl)phenyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 20 °C 3.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 7 h / 20 °C 3.2: 96 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 5.2: 20 °C
  • 5
  • [ 1246372-53-1 ]
  • 1-(2-Chloro-5-(4-((4-(2-methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)phenoxy)piperidin-1-yl)methyl)piperidine-1-carbonyl)phenyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 20 °C 3.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 7 h / 20 °C 3.2: 96 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 5.2: 48 h / 20 °C
  • 6
  • [ 1246372-53-1 ]
  • 1-(3-(4-((4-(2-Methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)phenoxy)piperidin-1-yl)methyl)piperidine-1-carbonyl)phenyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 20 °C 3.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 7 h / 20 °C 3.2: 96 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 5.2: 48 h / 20 °C
  • 7
  • [ 1246372-53-1 ]
  • 2-butyl-4-(3-methoxy-4-(piperidin-4-yloxy)phenyl)-2,7-naphthyridin-1(2H)-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / acetonitrile; water / 2 h / 100 °C 2: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C
  • 8
  • [ 1246372-53-1 ]
  • tert-butyl 4-((4-(4-(2-butyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)-2-methoxyphenoxy)piperidin-1-yl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / acetonitrile; water / 2 h / 100 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C 3.1: potassium carbonate; zinc(II) chloride / tetrahydrofuran; dimethyl sulfoxide / 0.5 h / 20 °C 3.2: 2 h / 20 °C
  • 9
  • [ 1246372-53-1 ]
  • 1-(5-(4-((4-(4-(2-butyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)-2-methoxyphenoxy)piperidin-1-yl)methyl)piperidine-1-carbonyl)-2-methoxyphenyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / acetonitrile; water / 2 h / 100 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C 3.1: potassium carbonate; zinc(II) chloride / tetrahydrofuran; dimethyl sulfoxide / 0.5 h / 20 °C 3.2: 2 h / 20 °C 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C
  • 10
  • [ 1246372-53-1 ]
  • 1-(5-(4-((4-(4-(2-butyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)-2-methoxyphenoxy)piperidin-1-yl)methyl)piperidine-1-carbonyl)-2-chlorophenyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C 2.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C 2.2: 20 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane; methanol / 4 h / 20 °C 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 5.2: 2 h / 20 °C
  • 11
  • [ 1246372-53-1 ]
  • 2-butyl-4-(3-methoxy-4-((1-(piperidin-4-ylmethyl)piperidin-4-yl)oxy)phenyl)-2,7-naphthyridin-1(2H)-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / acetonitrile; water / 2 h / 100 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C 3.1: potassium carbonate; zinc(II) chloride / tetrahydrofuran; dimethyl sulfoxide / 0.5 h / 20 °C 3.2: 2 h / 20 °C 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1 h / 20 °C
  • 12
  • [ 1246372-53-1 ]
  • 4-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidine hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.33 g With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 2h; 1.1 Step 1: 4-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidine To a 100 ml round bottom flask were added tert-butyl 4-(2-methoxy-4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenoxy)piperidine-1-carboxylate (intermediate 16, 5.48 g, 11.50 mmol), a solution of HCl (4 M) in 1,4-dioxane (15 ml) and MeOH (25 ml). The RM was stirred at RT for 2 h and concentrated. The residue was taken up in cold Et2O and the mixture was filtered, yielding the corresponding hydrochloride salt of the title compound as a solid (4.33 g). Method D: Rt = 0.77 min; [M+H]+= 334.
  • 13
  • [ 1246372-53-1 ]
  • tert-butyl 4-((4-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidin-1-yl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C 2.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C 2.2: 20 h / 20 °C
  • 14
  • [ 1246372-53-1 ]
  • 4-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-1-(piperidin-4-ylmethyl)piperidine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C 2.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C 2.2: 20 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane; methanol / 4 h / 20 °C
  • 15
  • [ 1246372-53-1 ]
  • 2-butyl-4-(3-methoxy-4-((1-(piperidin-4-ylmethyl)piperidin-4-yl)oxy)phenyl)-2,7-naphthyridin-1(2H)-one TFA salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C 2.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C 2.2: 20 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane; methanol / 4 h / 20 °C 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
  • 16
  • [ 1246372-53-1 ]
  • 4-bromo-2-butyl-2,7-naphthyridin-1(2H)-one [ No CAS ]
  • tert-butyl 4-(4-(2-butyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)-2-methoxyphenoxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
470 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; acetonitrile at 100℃; for 2h; 2.1 Step 1: tert-butyl 4-(4-(2-butyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)-2- methoxyphenoxy)piperidine-1-carboxylate To a 50 ml round bottom flask were added under an argin atmosphere tert-butyl 4-(2- methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidine-1-carboxylate (intermediate 16, 390 mg, 0.9 mmol), 4-bromo-2-butyl-2,7-naphthyridin-1(2H)-one (intermediate 32, 252 mg, 0.9 mmol), Na2CO3 (238 mg, 2.25 mmol), ACN (12 ml), water (3 ml) and PdCl2(dppf) (66 mg, 0.09 mmol). The RM was stirred at 100 °C for 2 h, the solvents were removed and the residue was purified by chromatography on silica gel eluting with EtOAc (from 0 % to 80 %) in PE, yielding the title compound as a solid (470 mg). Method E: Rt = 1.86 min; [M+H]+= 508.
  • 17
  • [ 1246372-53-1 ]
  • 4-(3-methoxy-4-(piperidin-4-yloxy)phenyl)-2-methyl-2,7-naphthyridin-1(2H)-one trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2: dichloromethane / 1 h / 20 °C
  • 18
  • [ 1246372-53-1 ]
  • tert-butyl 4-((4-(2-methoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)phenoxy)piperidin-1-yl)methyl)piperidine-1-carboxylate trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 20 °C 3.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 7 h / 20 °C 3.2: 96 h / 20 °C
  • 19
  • [ 1246372-53-1 ]
  • 4-(3-methoxy-4-((1-(piperidin-4-ylmethyl)piperidin-4-yl)oxy)phenyl)-2-methyl-2,7-naphthyridin-1(2H)-one trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 20 °C 3.1: zinc(II) chloride; triethylamine / tetrahydrofuran; methanol / 7 h / 20 °C 3.2: 96 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
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