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Product Details of [ 92352-29-9 ]

CAS No. :92352-29-9 MDL No. :MFCD06738755
Formula : C8H8N4 Boiling Point : -
Linear Structure Formula :- InChI Key :RJFHMLHZCNZQMA-UHFFFAOYSA-N
M.W : 160.18 Pubchem ID :6484152
Synonyms :

Calculated chemistry of [ 92352-29-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.22
TPSA : 67.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.35
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 1.06
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.76
Solubility : 2.78 mg/ml ; 0.0174 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 5.19 mg/ml ; 0.0324 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.157 mg/ml ; 0.000979 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 92352-29-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 92352-29-9 ]

* 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 [ 92352-29-9 ]

[ 92352-29-9 ] Synthesis Path-Downstream   1~54

  • 1
  • sodium 3-ethoxy-3-oxoprop-1-en-1-olate [ No CAS ]
  • [ 92352-29-9 ]
  • 2-Pyridin-2-yl-4H-pyrazolo[1,5-a]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In ethanol for 4h; Heating;
  • 2
  • [ 3788-94-1 ]
  • [ 92352-29-9 ]
  • [ 203587-57-9 ]
YieldReaction ConditionsOperation in experiment
50% In ethanol for 0.5h; Heating;
YieldReaction ConditionsOperation in experiment
88% With hydrazine hydrate In ethanol for 18h; Reflux; 2 Step 2 General procedure: To a solution of the proper compound III (1 eq.) in EtOH (0.2 - 1 M), the proper commercially available hydrazine IV (1 .2 eq.) was added and the mixture was heated at reflux for 18 h. After cooling to r.t., the mixture was concentrated under reduced pressure and purified to give the proper intermediate compound having general formula V.
60%
  • 4
  • [ 92352-29-9 ]
  • 7-Hydroxy-2-pyridin-2-yl-7H-1,4,7,9b-tetraaza-cyclopenta[a]naphthalen-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 50 percent / ethanol / 0.5 h / Heating 2: piperidine / toluene / 24 h / 80 - 90 °C 3: 92 percent / H2NOH*HCl, AcONa / acetic acid / 0.5 h / Heating
  • 5
  • [ 92352-29-9 ]
  • 7-((Z)-2-Dimethylamino-vinyl)-2-pyridin-2-yl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 50 percent / ethanol / 0.5 h / Heating 2: piperidine / toluene / 24 h / 80 - 90 °C
  • 6
  • [ 92352-29-9 ]
  • 7-((E)-2-Dimethylamino-vinyl)-2-pyridin-2-yl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 50 percent / ethanol / 0.5 h / Heating 2: piperidine / toluene / 24 h / 80 - 90 °C
  • 7
  • [ 92352-29-9 ]
  • 4-Ethyl-2-pyridin-2-yl-4H-pyrazolo[1,5-a]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 50 percent / ethanol / 4 h / Heating 2: 25 percent / K2CO3 / dimethylformamide / 6 h / 40 - 50 °C
  • 8
  • [ 67-56-1 ]
  • copper(II) bromide hydrate [ No CAS ]
  • [ 92352-29-9 ]
  • [CuBr(5-amino-3-(pyrid-2-yl)-1H-pyrazole)2]Br*MeOH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol CuBr2*99H2O treated with soln. of ligand in MeOH at -20°C; recrystd. from hot MeOH, dried in vac.; elem. anal.;
  • 9
  • [ 67-56-1 ]
  • copper(II) sulfate hydrate [ No CAS ]
  • [ 92352-29-9 ]
  • [Cu(H2O)(5-amino-3-(pyrid-2-yl)-1H-pyrazole)2]SO4*H2O*MeOH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol CuSO4*99H2O treated with soln. of ligand in MeOH at -20°C; recrystd. from hot MeOH, dried in vac.; elem. anal.;
  • 11
  • [ 54123-21-6 ]
  • [ 92352-29-9 ]
YieldReaction ConditionsOperation in experiment
91% With hydrazine In ethanol for 24h; Reflux; 52.A 3-(2-Pyridyl)-3-oxopropanenitrile (3.0 g, 0.37 mol) was dissolved in ethanol (22 mL) and treated with hydrazine (1.9 mL, 0.062 mol) at reflux for 24 hours. The reaction mixture was concentrated, diluted with brine and extracted into ethyl acetate (2 X 50 mL). The combined organic layers were dried (MgSO4), concentrated and purified by silica gel chromatography eluting with 2-20% methanol in methylene chloride to afford 3-(pyridin- 2-yl)-lH-pyrazol-5-amine (3.0 g, 91% yield).
64% With hydrazine hydrate In ethanol for 20h; Reflux; 52; 15 Preparation of Intermediate 36 [General Procedure 15]; [0275] General Procedure 15 was followed in the preparation of Intermediate 36. General ProcedurIntermediate 35 Intermediate 36[0276] Hydrazine hydrate (0.34 mL, 6.8 mmol, 1 eq) was added to a solution ofIntermediate 35 (1 g, 6.8 mmol) in EtOH (30 mL) at RT. The mixture was then heated to reflux and allowed to stir for 20 h. The solvent was then evaporated. The resulting crude material was triturated with Et20 (2 x 20 mL) and dried under vacuum to afford Intermediate 36 (700 mg, 64%) as a brown liquid. 1H NMR: (DMSO-d6) δ 8.53 (d, J= 4.4 Hz, 1H), 7.78 (d, J= 4.4 Hz, 2H), 7.23-7.26 (m, 1H), 5.95 (s, 1H), 4.84 (br s, 2H); MS: 161 [M + H]+; TLC: EtOAc: Rf: 0.20.
64% With hydrazine hydrate In ethanol at 78℃; for 20h; 31 Preparation of Intermediate 30 [General Procedure 18] 2317 [0269] General Procedure 18 was followed in the preparation of Intermediate 30. 318 General Procedure 15 2320 Intermediate 29 Intermediate 30 2321 [0270] Hydrazine hydrate (0.34 mL, 6.8 mmol, 1 eq) was added to a solution of 2322 Intermediate 29 (1 g, 6.8 mmol) in EtOH (30 mL) at RT. The mixture was then heated to 2323 reflux and allowed to stir for 20 h. The solvent was then evaporated. The resulting crude 2324 material was triturated with Et20 (2 x 20 mL) and dried under vacuum to afford Intermediate 2325 30 (700 mg, 64%) as a brown liquid. 1H NMR: (DMSO-d6) δ 8.53 (d, J= 4.4 Hz, 1H), 7.78 2326 (d, J= 4.4 Hz, 2H), 7.23-7.26 (m, 1H), 5.95 (s, 1H), 4.84 (br s, 2H); MS: 161 [M + H]+; TLC: 2327 EtOAc: Rf: 0.20.
64% With hydrazine hydrate In ethanol for 20h; Reflux; 52 General procedure: General Procedure 15 Hydrazine hydrate (0.34 mL, 6.8 mmol, 1 eq) was added to a solution of Intermediate 35 (1 g, 6.8 mmol) in EtOH (30 mL) at RT. The mixture was then heated to reflux and allowed to stir for 20 h. The solvent was then evaporated. The resulting crude material was triturated with Et2O (220 mL) and dried under vacuum to afford Intermediate 36 (700 mg, 64%) as a brown liquid. 1H NMR: (DMSO-d6) δ 8.53 (d, J=4.4 Hz, 1H), 7.78 (d, J=4.4 Hz, 2H), 7.23-7.26 (m, 1H), 5.95 (s, 1H), 4.84 (br s, 2H); MS: 161 [M+H]+; TLC: EtOAc: Rf: 0.20.
With sodium ethanolate; hydrazine hydrate In ethanol at 150℃; for 0.166667h; microwave irradiation; 20.1 There were dissolved, in ethanol (10 mL), 3-oxo-3-pyridin-2-yl-propane-nitrile (500 mg, 3.42 mM) and hydrazine monohydrate (199 μL, 4.10 mM) and the solution was stirred at 150° C. for 10 minutes under the irradiation with microwaves. The solvent was distilled off from this reaction liquid, the resulting residue was dissolved in ethanol (8 mL) and then sodium ethoxide (2M ethanol solution, 3.76 mL, 7.52 mM) and diethyl malonate (623 μL, 4.10 mM) were added to the solution. This reaction liquid was stirred at 150° C. for 50 minutes under the irradiation with microwaves. This reaction mixture was filtered and the resulting solid was washed with diethyl ether. Phosphoryl chloride (5 mL) was added to the resulting solid and the resulting suspension was stirred for 2 hours while refluxing the same with heating. The phosphoryl chloride was distilled off from this reaction liquid, ethanol was then added to the residue with ice-cooling and the mixture was stirred for 15 minutes. After the concentration of the reaction liquid, the resulting concentrate was purified by the silica gel column chromatography (methanol/methylene chloride=1:50 to 1:5) to thus give the title compound (378 mg, overall yield of these three steps: 34%). 1H-NMR (300 MHz, CD3OD): δ 7.62 (s, 1H), 7.65 (s, 1H), 8.10 (m, 1H), 8.72-8.74 (m, 2H), 8.89 (m, 1H); MS (ESI) m/z 265 (M+H)+.
With hydrazine hydrate; acetic acid In ethanol for 20h; Reflux; 180 To an ethanol (75 ml) solution of 3-oxo-3-(2-pyridinyl) propanenitrile (5 g) were added a hydrazine monohydrate (2.49 ml) solution and acetic acid (2.50 ml) at room temperature, and the mixture solution was refluxed under heating for 20 h. After the mixture was concentrated, the residue was diluted with ethyl acetate, and washed sequentially with water and with a saturated saline. After the organic layer was dried with anhydrous sodium sulfate, the organic layer was filtrated. After the filtrate was concentrated, the residue was purified by the silica gel column chromatography affording the compound 2 (2.51 g).MS m/z 161 [M+H]+, APCI(+)
630 mg With acetic acid; hydrazine In ethanol at 80℃; for 5h; 6.A Step A: 3-(Pyridin-2-yl)-lH-pyrazol-5-amine. To a solution of 3-oxo-3-(pyridin-2-yl)propanenitrile (1 g, 6.84 mmol) and hydrazine (513 mg, 10.24 mmol, 99%) in EtOH (35 mL) was added two drops of AcOH. The reaction was heated to 80 °C for 5 h. The reaction mixture was concentrated directly under reduced pressure. The resulting residue was purified by silica gel column chromatography with a gradient elution of 20% EtO Ac/PE to 33% EtO Ac/PE to provide 3-(pyridin-2-yl)-lH-pyrazol-5-amine (630 mg, 3.9 mmol) as white solid. LC-MS (ESI+): m/z 161 (MH+). NMR (300 MHz, DMSO-ifc) d 11.9 (brs, 1H), 8.53 (d, J= 4.8 Hz, 1H), 7.78-7.76 (m, 2H), 7.26-7.22 (m, 1H), 5.93 (s, 1H), 4.82 (brs, 2H).
1.34 g With hydrazine hydrate In ethanol Reflux; D.2: Synthesis of 3-(pyridin-2-yl)-lH-pyrazol-5-amine [0162] To a solution of 3-oxo-3-(pyridin-2-yl)propanenitrile (2.5 g, 17.1 mmol) in EtOH (75 mL) was added NH2NH2.H2O (1.71 g, 34.2 mmol). The reaction mixture was heated to reflux overnight. Upon the completion of the reaction as indicated by TLC analysis, the reaction mixture was concentrated directly and purified by silica gel column chromatography with a gradient elution of 1% MeOH/DCM to 3% MeOH/DCM to provide 3-(pyridin-2-yl)-lH-pyrazol-5-amine (1.34 g, 8.37 mmol) as a brown solid. LC-MS (ESI+): m/z 161 (MH+). 1HNMR (300 MHz, CDCb) S: 8.58 (d, J = 4.2 Hz, 1H), 7.75-7.69 (m, 1H), 7.52 (d, J= 8.1 Hz, 1H), 7.24-7.20 (m, 1H), 6.09 (s, 1H).

  • 12
  • [ 2940-26-3 ]
  • [ 92352-29-9 ]
  • [ 1186609-04-0 ]
YieldReaction ConditionsOperation in experiment
88% In water at 100℃; 52.B A 50 mL reaction vessel was charged with 3-(pyridin-2-yl)-lH- pyrazol-5 -amine (1.5 g, 9.4 mmol), sodium nitromalonaldehyde monohydrate (1.54 g, 9.8 mmol) and water (9 mL). The flask was heated to 100°C overnight, and the cooled reaction mixture was extracted with ethyl acetate (3 X 25 mL). The combined organic layers were dried (MgSO4), to provide crude 3-(pyridin-2-yl)-5-nitro-lH-pyrazolo[3,4-b]pyridine (2.0 g, 88% yield) as a solid.
  • 13
  • [ 2524-52-9 ]
  • [ 92352-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / toluene; mineral oil / 16 h / 65 °C 2: hydrazine hydrate / ethanol / 20 h / Reflux
Multi-step reaction with 2 steps 1: sodium hydride / toluene; mineral oil / 16 h / 65 °C 2: hydrazine hydrate / ethanol / 20 h / 78 °C
Multi-step reaction with 2 steps 1: mineral oil; toluene / 16 h / 65 °C 2: hydrazine hydrate / ethanol / 20 h / Reflux
  • 14
  • [ 98-98-6 ]
  • [ 92352-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 0 °C / Reflux 2: sodium hydride / toluene; mineral oil / 16 h / 65 °C 3: hydrazine hydrate / ethanol / 20 h / Reflux
Multi-step reaction with 3 steps 1: thionyl chloride / 2 h / 0 - 78 °C 2: sodium hydride / toluene; mineral oil / 16 h / 65 °C 3: hydrazine hydrate / ethanol / 20 h / 78 °C
Multi-step reaction with 3 steps 1: thionyl chloride / ethanol / 2 h / 0 °C / Reflux 2: mineral oil; toluene / 16 h / 65 °C 3: hydrazine hydrate / ethanol / 20 h / Reflux
  • 15
  • [ 105-53-3 ]
  • [ 92352-29-9 ]
  • [ 1232223-43-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: diethyl malonate; 3{5}-amino-5{3}-(pyrid-2-yl)-1H-pyrazole With sodium ethanolate In ethanol at 150℃; for 50h; microwave irradiation; Stage #2: With trichlorophosphate for 2h; Reflux; 20.1 There were dissolved, in ethanol (10 mL), 3-oxo-3-pyridin-2-yl-propane-nitrile (500 mg, 3.42 mM) and hydrazine monohydrate (199 μL, 4.10 mM) and the solution was stirred at 150° C. for 10 minutes under the irradiation with microwaves. The solvent was distilled off from this reaction liquid, the resulting residue was dissolved in ethanol (8 mL) and then sodium ethoxide (2M ethanol solution, 3.76 mL, 7.52 mM) and diethyl malonate (623 μL, 4.10 mM) were added to the solution. This reaction liquid was stirred at 150° C. for 50 minutes under the irradiation with microwaves. This reaction mixture was filtered and the resulting solid was washed with diethyl ether. Phosphoryl chloride (5 mL) was added to the resulting solid and the resulting suspension was stirred for 2 hours while refluxing the same with heating. The phosphoryl chloride was distilled off from this reaction liquid, ethanol was then added to the residue with ice-cooling and the mixture was stirred for 15 minutes. After the concentration of the reaction liquid, the resulting concentrate was purified by the silica gel column chromatography (methanol/methylene chloride=1:50 to 1:5) to thus give the title compound (378 mg, overall yield of these three steps: 34%). 1H-NMR (300 MHz, CD3OD): δ 7.62 (s, 1H), 7.65 (s, 1H), 8.10 (m, 1H), 8.72-8.74 (m, 2H), 8.89 (m, 1H); MS (ESI) m/z 265 (M+H)+.
  • 16
  • [ 92352-29-9 ]
  • [ 1232220-49-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium ethanolate / ethanol / 50 h / 150 °C / microwave irradiation 1.2: 2 h / Reflux 2.1: 1,4-dioxane / 0.33 h / 1 - 30 °C 3.1: potassium carbonate; hydrazine hydrate / ethanol / 0.33 h / 150 °C / microwave irradiation 4.1: acetic acid / ethanol / 0.5 h / 1 - 30 °C 4.2: NH-silica gel
  • 17
  • [ 92352-29-9 ]
  • [ 1232223-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium ethanolate / ethanol / 50 h / 150 °C / microwave irradiation 1.2: 2 h / Reflux 2.1: 1,4-dioxane / 0.33 h / 1 - 30 °C
Multi-step reaction with 3 steps 1: ethanol; sodium / 110 °C 2: P,P-dichlorophenylphosphine oxide / 110 °C 3: 1,4-dioxane / 1 h / 20 °C
  • 18
  • [ 92352-29-9 ]
  • [ 1232220-78-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium ethanolate / ethanol / 50 h / 150 °C / microwave irradiation 1.2: 2 h / Reflux 2.1: 1,4-dioxane / 0.33 h / 1 - 30 °C 3.1: potassium carbonate; hydrazine hydrate / ethanol / 0.33 h / 150 °C / microwave irradiation 4.1: acetic acid / ethanol / 1 h / 1 - 30 °C 4.2: NH-silica gel
  • 19
  • [ 92352-29-9 ]
  • [ 1232220-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium ethanolate / ethanol / 50 h / 150 °C / microwave irradiation 1.2: 2 h / Reflux 2.1: 1,4-dioxane / 0.33 h / 1 - 30 °C 3.1: potassium carbonate; hydrazine hydrate / ethanol / 0.33 h / 150 °C / microwave irradiation 4.1: acetic acid / ethanol / 0.5 h / 1 - 30 °C 4.2: NH-silica gel
  • 20
  • [ 92352-29-9 ]
  • C15H17N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium ethanolate / ethanol / 50 h / 150 °C / microwave irradiation 1.2: 2 h / Reflux 2.1: 1,4-dioxane / 0.33 h / 1 - 30 °C 3.1: potassium carbonate; hydrazine hydrate / ethanol / 0.33 h / 150 °C / microwave irradiation
  • 21
  • [ 2516-99-6 ]
  • [ 124-41-4 ]
  • [ 92352-29-9 ]
  • [ 1411693-24-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,3,3-Trifluoropropionic acid With trichlorophosphate In N,N-dimethyl-formamide for 4h; Stage #2: sodium methylate; 3{5}-amino-5{3}-(pyrid-2-yl)-1H-pyrazole In acetonitrile at 0 - 20℃; 180 DMF was heated to 50° C., and 3,3,3-trifluoropropionic acid (1.5 ml) was added thereto and the solution was stirred. The mixture was heated to 70° C., and phosphorus oxychloride (2.60 ml) was added thereto by drops for 1 h. After the mixture was stirred for 3 h, the reaction solution was concentrated i vacuo. The residue was dissolved in acetonitrile (6 ml), and at 0° C., the compound 2 (300 mg) and sodium methoxide (546 mg) were added slowly. After the reaction solution was stirred at room temperature for 2 h, an insoluble material was filtrated and diluted by ethyl acetate. The organic layer was washed sequentially with water and with a saturated saline. The organic layer was dried with anhydrous sodium sulfate and filtrated The filtrate was concentrated, and the residue was purified by the silica gel column chromatography affording the compound 3 (125 mg) was obtained.MS m/z 265 [M+H]+, APCI(+)
  • 22
  • [ 92352-29-9 ]
  • [ 1312308-63-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 4 h 1.2: 0 - 20 °C 2.1: N-iodo-succinimide / acetonitrile / 3 h / 50 °C 3.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 20 h / 90 °C / Inert atmosphere
  • 23
  • [ 92352-29-9 ]
  • [ 1411693-81-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 4 h 1.2: 0 - 20 °C 2.1: N-iodo-succinimide / acetonitrile / 3 h / 50 °C
  • 24
  • tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]
  • C40H34IrN3O5S [ No CAS ]
  • [ 92352-29-9 ]
  • C36H28IrN6O4(1+)*C32H12BF24(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: C40H34IrN3O5S; 3{5}-amino-5{3}-(pyrid-2-yl)-1H-pyrazole With ammonium hexafluorophosphate In acetonitrile at 65℃; Inert atmosphere; Darkness; Stage #2: tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Darkness;
  • 25
  • [ 407-25-0 ]
  • [ 92352-29-9 ]
  • [ 1437326-50-5 ]
YieldReaction ConditionsOperation in experiment
73% With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
  • 26
  • [ 123-72-8 ]
  • [ 92352-29-9 ]
  • [ 1437326-51-6 ]
YieldReaction ConditionsOperation in experiment
23% With sodium tris(acetoxy)borohydride In dichloromethane at 60℃; Inert atmosphere;
  • 28
  • [ 4422-95-1 ]
  • [ 92352-29-9 ]
  • [ 1610948-36-1 ]
YieldReaction ConditionsOperation in experiment
52% In acetonitrile Reflux;
  • 29
  • [ 3739-94-4 ]
  • [ 92352-29-9 ]
  • N<SUP>2</SUP>,N<SUP>6</SUP>-bis(3-(pyridin-2-yl)-1H-pyrazole-5-yl)pyridine-2,6-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In acetonitrile Reflux;
  • 30
  • [ 92352-29-9 ]
  • phenyl (4-chloro-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2: pyridine / 12 h / 0 - 20 °C / Inert atmosphere
  • 31
  • [ 92352-29-9 ]
  • 1-(3-chlorophenyl)methyl-3-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 32
  • [ 92352-29-9 ]
  • 1-benzyl-3-(4-chloro-3-(pyridin-2-yl)-1H-pyrazol-5-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 3: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 33
  • [ 92352-29-9 ]
  • 4-phenyl-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 34
  • [ 92352-29-9 ]
  • 4-chloro-3-(pyridin-2-yl)-1H-pyrazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With N-chloro-succinimide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
  • 35
  • [ 92352-29-9 ]
  • 4-(4-fluorophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 36
  • [ 92352-29-9 ]
  • 4-(3-fluorophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 37
  • [ 92352-29-9 ]
  • 4-(4-chlorophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 38
  • [ 92352-29-9 ]
  • 4-(3-chlorophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 39
  • [ 92352-29-9 ]
  • 4-(4-cyanophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 40
  • [ 92352-29-9 ]
  • 4-phenoxy-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 41
  • [ 92352-29-9 ]
  • 4-(4-cyanophenoxy)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 42
  • [ 92352-29-9 ]
  • N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-4-(pyridin-2-yloxy)piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 43
  • [ 92352-29-9 ]
  • 4-(4-fluorophenyl)-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-piperazine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / chloroform / 16 h / Inert atmosphere; Reflux
  • 44
  • 3-isopropoxy-5-(pyrrolidine-1-carbonyl)benzoyl chloride [ No CAS ]
  • [ 92352-29-9 ]
  • 3-isopropoxy-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-5-(pyrrolidine-1-carbonyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In acetonitrile for 16h; Inert atmosphere; Reflux;
  • 48
  • ammonium hexafluorophosphate [ No CAS ]
  • (S),Λ-Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2((S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)phenol) [ No CAS ]
  • [ 92352-29-9 ]
  • C32H18F10IrN6(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In acetonitrile at 65℃; for 5h; Inert atmosphere; Darkness;
  • 49
  • [ 92352-29-9 ]
  • [ 1186609-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water / 100 °C 2: tin(ll) chloride / methanol; ethyl acetate / 3 h / Heating; Reflux
  • 50
  • [ 13360-57-1 ]
  • [ 92352-29-9 ]
  • 5-amino-N,N-dimethyl-3-(pyridin-2-yl)-1H-pyrazole-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
310 mg Stage #1: 3{5}-amino-5{3}-(pyrid-2-yl)-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran 6.B Step B: 5-Amino-N,N-dimethyl-3-(pyridin-2-yl)-lH-pyrazole-l-sulfonamide. To a solution of 3-(pyridin-2-yl)-lH-pyrazol-5-amine (630 mg, 3.94 mmol) in THF (5 mL) at 0 °C was added NaH (315 mg, 7.88 mmol). After stirring at 0 °C for 1 h, to the solution was added dimethyl sulfamoyl chloride (676 mg, 4.72 mmol). The reaction mixture was quenched with saturated aq. MbCl. The aqueous solution was extracted with ethyl acetate (3 x 50 mL). The combined organic phase was dried over anhydrous Na2SC>4, filtrated, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with a gradient elution of 20% EtO Ac/PE to 33% EtO Ac/PE to provide the title compound (310 mg, 1.16 mmol). LC-MS (ESI+): m/z 268 (MH+). NMR (300 MHz, CDCb) d 8.59 (d, J= 5.7 Hz, 1H), 8.04 (d, 7= 8.1 Hz, 1H), 7.72 (td, 7= 7.8, 1.8 Hz, 1H), 7.25-7.22 (m, 1H), 6.11 (s, 1H), 4.89 (brs, 2H), 3.02 (s, 6H).
  • 51
  • [ 92352-29-9 ]
  • N,N-dimethyl-5-((4-morpholinopyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl)amino)-3-(pyridin-2-yl)-1H-pyrazole-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; caesium carbonate / N,N-dimethyl-formamide; 1,4-dioxane / 0.67 h / 90 °C / Microwave irradiation
  • 52
  • [ 105-53-3 ]
  • [ 92352-29-9 ]
  • 2-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol; sodium at 110℃; D.3: Synthesis of 2-(pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-5,7(4H,6H)-dione [0164] To a solution of anhydrous EtOH (10 mL) was added small pieces of sodium (580 mg, 25.2 mmol) at ambient temperature carefully. After all of the sodium was dissolved, the solution was concentrated to provide fresh NaOEt as a white solid. The freshly prepared NaOEt was added to a mixture of diethyl malonate (40 mL) and 3-(pyridin-2-yl)-lH-pyrazol-5-amine (1.34 g, 8.37 mmol). The mixture was heated to 110 °C and stirred at that temperature overnight. After the reaction mixture was cooled to ambient temperature, a large amount of solid was precipitated. After filtration, the filter cake was washed with diethyl ether twice to provide crude 2-(pyridin-2- yl)pyrazolo[l,5-a]pyrimidine -5,7(4H,6H)-dione (3.89 g, 17.1 mg) as a yellow solid. The crude product was used directly for the next step without further purification. LC-MS (ESI+): 229 (MH+).
  • 53
  • [ 92352-29-9 ]
  • [ 1232223-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol; sodium / 110 °C 2: P,P-dichlorophenylphosphine oxide / 110 °C
  • 54
  • [ 92352-29-9 ]
  • 4-(2-(pyridin-2-yl)-5-(3-(m-tolyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ethanol; sodium / 110 °C 2: P,P-dichlorophenylphosphine oxide / 110 °C 3: 1,4-dioxane / 1 h / 20 °C 4: caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 120 °C
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