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[ CAS No. 170572-48-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 170572-48-2
Chemical Structure| 170572-48-2
Chemical Structure| 170572-48-2
Structure of 170572-48-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 170572-48-2 ]

CAS No. :170572-48-2 MDL No. :MFCD03094192
Formula : C7H5F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRGQSKODTJDDHT-UHFFFAOYSA-N
M.W : 173.12 Pubchem ID :2774183
Synonyms :

Calculated chemistry of [ 170572-48-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.15
TPSA : 45.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 3.02
Log Po/w (MLOGP) : 2.87
Log Po/w (SILICOS-IT) : 0.98
Consensus Log Po/w : 2.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.363 mg/ml ; 0.00209 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.208 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.33 mg/ml ; 0.00191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 170572-48-2 ]

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

Application In Synthesis of [ 170572-48-2 ]

* 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 [ 170572-48-2 ]

[ 170572-48-2 ] Synthesis Path-Downstream   1~33

  • 1
  • 1,3-difluoro-2-methyl-5-nitrobenzene [ No CAS ]
  • [ 100644-65-3 ]
  • 4-chloro-1-[(2,6-difluoro-4-nitrophenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: 1,3-difluoro-2-methyl-5-nitrobenzene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 15h; Stage #2: 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine With potassium carbonate In tetrachloromethane; N,N-dimethyl acetamide at 80℃; for 3h; 1.46.1 Stage 1: Production of 4-chloro-1-[(2,6-difluoro-4-nitro-phenyl)methyl] pyrazolo[3,4-d]pyrimidin-6-amine (intermediate compound S112) To the solution of 1,3-difluoro-2-methyl-5-nitro-benzene (2 g, 11.55 mmol, 1 eq) in tetrachloromethane (50 mL) were added NBS (3.08 g, 17.33 mmol, 1.5 eq) and AIBN (190 mg, 1.16 mmol, 0.1 eq). Then the mixture was stirred at 90 °C for 15 h. The reaction mixture was concentrated in vacuum to give a residue. To the residue was added DMAc (50 mL), 4- chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (1.96 g, 11.55 mmol, 1 eq) and K2CO3 (3.19 g, 23.11 mmol, 2 eq). Then the mixture was stirred at 80 °C for 3 h. To the mixture was added water (130 mL) and ethyl acetate (130 mL), and the layers were separated. The aqueous was extracted with ethyl acetate (130 mL x 2). Combined the organic phase to wash by brines (150 mL x 2), dry over anhydrous sodium sulfate, filter and the filtrate was concentrated in vacuum to give a residue. The residue was purified by flash silica gel chromatography (40 g SepaFlash Silica Flash Column, Eluent of 0~30% Ethyl acetate/Petroleum ether gradient 60 mL/min). Intermediate compound S112 or 4-chloro-1-[(2,6-difluoro-4-nitro-phenyl) methyl]pyrazolo[3,4-d]pyrimidin-6-amine (1.5 g, 4.26 mmol, 37% yield, 96.7% purity) was obtained as a yellow solid.
  • 2
  • [ 170572-48-2 ]
  • [ 2645363-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 2 h / 110 °C / Microwave irradiation; Sealed tube 4: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 1 h / 80 °C
  • 3
  • [ 170572-48-2 ]
  • [ 2645364-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C
  • 4
  • [ 170572-48-2 ]
  • [ 1260879-41-1 ]
YieldReaction ConditionsOperation in experiment
With NBS; azobisisobutyronitrile In Carbon tetrachloride at 90℃; for 15h; 1.10.1 Stage 1: Production of 4-chloro-1-r(2.6-difluoro-4-nitro-phenyl)methyll pyrazolo[3.4- d]pyriniidine-6-amine (intermediate compound S12) To the solution of 1,3-difluoro-2-methyl-5-nitro-benzene (2 g, 11.55 mmol, 1 eq) in tetrachloromethane (50 mL) were added NBS (3.08 g, 17.33 mmol, 1.5 eq) and AIBN (190 mg, 1.16 mmol, 0.1 eq). Then the mixture was stirred at 90 °C for 15 h. The reaction mixture was concentrated in vacuum to give a residue. To the residue was added DMAc (50 mL), 4-chloro- lH-pyrazolo[3,4-d]pyrimidine-6-amine (1.96 g, 11.55 mmol, 1 eq) and K2CO3 (3.19 g, 23.11 mmol, 2 eq). Then the mixture was stirred at 80 °C for 3 h. To the mixture was added water (130 mL) and ethyl acetate (130 mL), and the layers were separated. The aqueous was extracted with ethyl acetate (130 mL x 2). Combined the organic phase to wash by brines (150 mL x 2), dry over anhydrous sodium sulfate, filter and the filtrate was concentrated in vacuum to give a residue. The residue was purified by flash silica gel chromatography (40 g SepaFlash Silica Flash Column, Eluent of 0~30% Ethyl acetate/Petroleum ether gradient 60 mL/min). Intermediate compound S12 or 4-chloro-1-[(2,6-difluoro-4-nitro-phenyl) methyl]pyrazolo[3,4- d]pyrimidine-6-amine (1.5 g, 4.26 mmol, 37% yield, 96.7% purity) was obtained as a yellow solid.
With NBS; azobisisobutyronitrile In Carbon tetrachloride at 90℃; for 15h; 1.10.1 Stage 1: Production of 4-chloro-1-r(2.6-difluoro-4-nitro-phenyl)methyll pyrazolo[3.4- d]pyriniidine-6-amine (intermediate compound S12) To the solution of 1,3-difluoro-2-methyl-5-nitro-benzene (2 g, 11.55 mmol, 1 eq) in tetrachloromethane (50 mL) were added NBS (3.08 g, 17.33 mmol, 1.5 eq) and AIBN (190 mg, 1.16 mmol, 0.1 eq). Then the mixture was stirred at 90 °C for 15 h. The reaction mixture was concentrated in vacuum to give a residue. To the residue was added DMAc (50 mL), 4-chloro- lH-pyrazolo[3,4-d]pyrimidine-6-amine (1.96 g, 11.55 mmol, 1 eq) and K2CO3 (3.19 g, 23.11 mmol, 2 eq). Then the mixture was stirred at 80 °C for 3 h. To the mixture was added water (130 mL) and ethyl acetate (130 mL), and the layers were separated. The aqueous was extracted with ethyl acetate (130 mL x 2). Combined the organic phase to wash by brines (150 mL x 2), dry over anhydrous sodium sulfate, filter and the filtrate was concentrated in vacuum to give a residue. The residue was purified by flash silica gel chromatography (40 g SepaFlash Silica Flash Column, Eluent of 0~30% Ethyl acetate/Petroleum ether gradient 60 mL/min). Intermediate compound S12 or 4-chloro-1-[(2,6-difluoro-4-nitro-phenyl) methyl]pyrazolo[3,4- d]pyrimidine-6-amine (1.5 g, 4.26 mmol, 37% yield, 96.7% purity) was obtained as a yellow solid.
  • 5
  • [ 170572-48-2 ]
  • [ 2645364-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 2 h / 110 °C / Microwave irradiation; Sealed tube
  • 6
  • [ 170572-48-2 ]
  • [ 2645363-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 15 h / 110 °C 4: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 1 h / 80 °C
  • 7
  • [ 170572-48-2 ]
  • [ 2645364-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 15 h / 110 °C
  • 8
  • [ 170572-48-2 ]
  • [ 2645363-50-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / Heating 4: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 2 h / 80 °C
  • 9
  • [ 170572-48-2 ]
  • [ 2645364-27-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / Heating
  • 10
  • [ 170572-48-2 ]
  • [ 2645363-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: tricyclohexylphosphine; C4H6O4Pd(2+); potassium carbonate / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 4: iron(0); ammonia hydrochloride / tetrahydrofuran; lithium hydroxide monohydrate / 5 h / 80 °C
  • 11
  • [ 170572-48-2 ]
  • [ 2645364-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: tricyclohexylphosphine; C4H6O4Pd(2+); potassium carbonate / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
  • 12
  • [ 170572-48-2 ]
  • [ 2645363-59-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 3 h / 80 °C 4: tricyclohexylphosphine; C4H6O4Pd(2+); potassium carbonate / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
  • 13
  • [ 170572-48-2 ]
  • [ 2645364-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 3 h / 80 °C
  • 14
  • [ 170572-48-2 ]
  • [ 2645363-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 15 h / 100 °C 4: iron(0); ammonia hydrochloride / lithium hydroxide monohydrate; ethanol / 2 h / 80 °C
  • 15
  • [ 170572-48-2 ]
  • [ 2645364-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS; azobisisobutyronitrile / Carbon tetrachloride / 15 h / 90 °C 2: potassium carbonate / N,N-dimethyl acetamide / 3 h / 80 °C 3: potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 15 h / 100 °C
  • 16
  • [ 170572-48-2 ]
  • [ 878285-13-3 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; for 3h; 1.2 Step 2 To a solution of 1 ,3-difluoro-2-methyl-5-nitrobenzene (500 mg, 2.89 mmol, 1 .00 eq) in tetra hydrofuran (5.00 mL) was added palladium on carbon (80.0 mg, 1 0% purity). The mixture was stirred under hydrogen at 25 °C for 3 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to afford 3,5-difluoro-4-methylaniline. ’ H NMR (400 MHz, DMSO-d 6) δ= 6.1 6 (d, J= 10.0 Hz, 2H), 5.45 (s, 2H), 2.55 - 2.46 (m, 3H).
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; for 3h; 1.2 Step 2 To a solution of 1 ,3-difluoro-2-methyl-5-nitrobenzene (500 mg, 2.89 mmol, 1 .00 eq) in tetra hydrofuran (5.00 mL) was added palladium on carbon (80.0 mg, 1 0% purity). The mixture was stirred under hydrogen at 25 °C for 3 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to afford 3,5-difluoro-4-methylaniline. ’ H NMR (400 MHz, DMSO-d 6) δ= 6.1 6 (d, J= 10.0 Hz, 2H), 5.45 (s, 2H), 2.55 - 2.46 (m, 3H).
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; for 3h; 2.2 Step 2: To a solution of 1 ,3-difluoro-2-methyl-5-nitrobenzene (500 mg, 2.89 mmol, 1 .00 eq) in tetrahydrofuran (5.00 mL) was added palladium on carbon (80.0 mg, 10% purity). The mixture was stirred under hydrogen at 25 °C for 3 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to afford 3,5-difluoro-4-methylaniline.1H NMR (400 MHz, DMSO-dO 5= 6.16 (d, J= 10.0 Hz, 2H), 5.45 (s, 2H), 2.55 - 2.46 (m, 3H).
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; for 3h; 2.2 Step 2: To a solution of 1 ,3-difluoro-2-methyl-5-nitrobenzene (500 mg, 2.89 mmol, 1 .00 eq) in tetrahydrofuran (5.00 mL) was added palladium on carbon (80.0 mg, 10% purity). The mixture was stirred under hydrogen at 25 °C for 3 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to afford 3,5-difluoro-4-methylaniline.1H NMR (400 MHz, DMSO-dO 5= 6.16 (d, J= 10.0 Hz, 2H), 5.45 (s, 2H), 2.55 - 2.46 (m, 3H).

  • 17
  • [ 170572-48-2 ]
  • [ 2803883-52-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 25 °C 2: pyridine / acetonitrile / 3 h / 25 °C
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 25 °C 2: pyridine / acetonitrile / 3 h / 25 °C
  • 18
  • [ 170572-48-2 ]
  • [ 2803880-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 25 °C 2: pyridine / acetonitrile / 3 h / 25 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 25 °C
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 25 °C 2: pyridine / acetonitrile / 3 h / 25 °C 3: sodium hydride / N,N-dimethyl-formamide / 1 h / 25 °C
  • 19
  • [ 2935-90-2 ]
  • [ 170572-48-2 ]
  • [ 2778374-29-9 ]
YieldReaction ConditionsOperation in experiment
56.8% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 60℃; for 8h; Inert atmosphere; 1.1 Step 1: Synthesis of methyl 3-((3-fluoro-2-methyl-5-nitrophenyl)thio)propanoate Add A1-a (1.73g, 10mmol, 1eq) to a 50mL three-necked flask,Methyl 3-mercaptopropionate (1.8g, 15mmol, 1.5eq)and NMP (10mL),After the system was dissolved, potassium carbonate (2g, 15mmol, 1.5eq) was added,Stir under argon at 60°C for 8h.After cooling to room temperature,Add water (30mL) to dilute the system,The precipitated solid was filtered, washed with water,Filter cake column chromatography (PE/EA=1/12-1/7) gave yellow solid A2-a (1.55g,yield 56.8%), LC-MS: 274.2 [M+H]+.
  • 20
  • [ 170572-48-2 ]
  • [ 2820043-34-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate 10.1: 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 °C
  • 21
  • [ 170572-48-2 ]
  • [ 2820044-46-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate 10.1: 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 °C
  • 22
  • [ 170572-48-2 ]
  • [ 2820045-13-2 ]
  • [ 2820045-08-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate 10.1: 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 °C
  • 23
  • [ 170572-48-2 ]
  • [ 2820043-85-2 ]
  • [ 2820043-91-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate 10.1: 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 °C
  • 24
  • [ 170572-48-2 ]
  • [ 2778374-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere
  • 25
  • [ 170572-48-2 ]
  • [ 2778373-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
  • 26
  • [ 170572-48-2 ]
  • [ 2778374-30-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere
  • 27
  • [ 170572-48-2 ]
  • [ 2778374-31-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere
  • 28
  • [ 170572-48-2 ]
  • [ 2778374-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice
  • 29
  • [ 170572-48-2 ]
  • [ 2778374-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate
  • 30
  • [ 170572-48-2 ]
  • [ 2778374-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate
  • 31
  • [ 170572-48-2 ]
  • [ 2778373-95-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere 7.1: glacial acetic acid; p-toluenesulfonic acid monohydrate; magnesium(II) sulfate / 24 h / 105 °C / Inert atmosphere 8.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane / 24 h / 80 °C / Inert atmosphere 9.1: trifluoroacetic acid / lithium hydroxide monohydrate; acetonitrile / Resolution of racemate 10.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / Cooling with ice
  • 32
  • [ 170572-48-2 ]
  • [ 2778374-33-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C
  • 33
  • [ 170572-48-2 ]
  • [ 2778374-34-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 8 h / 60 °C / Inert atmosphere 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 16 h / 90 °C / Inert atmosphere 2.2: 4 h / 65 °C / Inert atmosphere 3.1: Eaton′s reagent / 1 h / 60 °C / Inert atmosphere 4.1: N,N-dimethyl-4-aminopyridine; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 5.1: potassium-t-butoxide; n-Butyl nitrite / tetrahydrofuran / 2 h / -20 - 5 °C 5.2: 2.08 h / 20 °C 6.1: hydrogenchloride / lithium hydroxide monohydrate; 1,4-dioxane; methanol / 2 h / 40 °C / Inert atmosphere
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