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[ CAS No. 10199-50-5 ]

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Chemical Structure| 10199-50-5
Chemical Structure| 10199-50-5
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Product Details of [ 10199-50-5 ]

CAS No. :10199-50-5 MDL No. :MFCD00067874
Formula : C10H11N3 Boiling Point : 368.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :173.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 10199-50-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10199-50-5 ]

  • Downstream synthetic route of [ 10199-50-5 ]

[ 10199-50-5 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 108-94-1 ]
  • [ 10199-50-5 ]
  • [ 91623-40-4 ]
YieldReaction ConditionsOperation in experiment
54.26% With acetic acid; at 50℃;Inert atmosphere; Under nitrogen atmosphere, to a 100 mL of round bottom flask were added 1-methyl-3-phenyl-5-amino-1-hydro-pyrozole (5g, 28mmol) and 40 mL of glacial acetic acid. 1-methyl-3-phenyl-5-amino-1-hydro-pyrozole was dissolved with stirring. Cyclohexanone (5.6g, 57mmol) was added to obtain a resultant mixture. The mixture was warmed to 50C with stirring. The reaction was kept warm overnight. The reaction was stopped. The solvent was rotary-evaporated. An appropriate amount of ethyl acetate was added. The mixture was washed to be natural with aqueous solution of sodium bicarbonate. The ethyl acetate layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined. The combined organic phase was dried over MgSO4. The solvent was rotary-evaporated. The crude product was purified by column chromatography to give 4.4 g of the pure title compound. Yield: 54.26%. MS (ESI): m/z 254 (M+H)+
54.26% With acetic acid; at 50℃;Inert atmosphere; Example 3A 1-methyl-3-phenyl-4-cyclohexenyl-5-amino-1H-pyrazole Under nitrogen atmosphere, to a 100 mL of round bottom flask were added 1-methyl-3-phenyl-5-amino-1-hydro-pyrozole (5 g, 28 mmol) and 40 mL of glacial acetic acid. 1-methyl-3-phenyl-5-amino-1-hydro-pyrozole was dissolved with stirring. Cyclohexanone (5.6 g, 57 mmol) was added to obtain a resultant mixture. The mixture was warmed to 50 C. with stirring. The reaction was kept warm overnight. The reaction was stopped. The solvent was rotary-evaporated. An appropriate amount of ethyl acetate was added. The mixture was washed to be natural with aqueous solution of sodium bicarbonate. The ethyl acetate layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined. The combined organic phase was dried over MgSO4. The solvent was rotary-evaporated. The crude product was purified by column chromatography to give 4.4 g of the pure title compound. Yield: 54.26%. MS (ESI): m/z 254 (M+H)+
  • 2
  • [ 5436-21-5 ]
  • [ 10199-50-5 ]
  • [ 116835-07-5 ]
  • 3
  • [ 898-22-6 ]
  • [ 10199-50-5 ]
  • 1-Methyl-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-dicarboxylic acid diethyl ester [ No CAS ]
  • 4
  • [ 653-37-2 ]
  • [ 10199-50-5 ]
  • 5,6,7,8-tetrafluoro-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline [ No CAS ]
  • 5
  • [ 10199-50-5 ]
  • [ 132026-42-7 ]
  • 6
  • [ 623-00-7 ]
  • [ 10199-50-5 ]
  • C17H14N4 [ No CAS ]
  • 7
  • [ 623-03-0 ]
  • [ 10199-50-5 ]
  • C17H14N4 [ No CAS ]
  • 8
  • [ 5798-75-4 ]
  • [ 10199-50-5 ]
  • C19H19N3O2 [ No CAS ]
  • 9
  • [ 614-16-4 ]
  • [ 60-34-4 ]
  • [ 10199-50-5 ]
YieldReaction ConditionsOperation in experiment
71% In methanol; at 110℃; for 1.5h;microwave irradiation; A mixture of benzoyl acetonitrile (2.0 g, 13.778 mmol) and methyl hydrazine (0.698, 15.156 mmol) in methanol (10 ml_) was irradiated under microwave conditions at 110 C for 90 min. The reaction mixture was cooled to rt and poured into rapidly stirred ice cold water. The obtained solid was collected by filtration, dried under vacuum and triturated with a mixture of pentane-hexane (-10 mL) to yield a white solid (1.7g, 71 %). [1H-NMR (CDCI3, 300 MHz) δ 7.82-7.65 (m, 2H), 7.45-7.20 (m, 3H), 5.90 (s, 1 H), 3.75 (s, 3H), 3.55 (s, 2H); LCMS RtA = 0.824 min; [M+H]+ = 174.1 ]
71% In methanol; at 20 - 110℃; for 1.5h;Microwave Irradiation; b) 1-methyl-3-phenyl-1H-pyrazol-5-amine A mixture of benzoyl acetonitrile (2.0 g, 13.778 mmol) and methyl hydrazine (0.698, 15.156 mmol) in methanol (10 mL) was irradiated under microwave conditions at 110 C. for 90 min. The reaction mixture was cooled to rt and poured into rapidly stirred ice cold water. The obtained solid was collected by filtration, dried under vacuum and triturated with a mixture of pentane-hexane (10 mL) to yield a white solid (1.7 g, 71%). [1H-NMR (CDCl3, 300 MHz) δ 7.82-7.65 (m, 2H), 7.45-7.20 (m, 3H), 5.90 (s, 1H), 3.75 (s, 3H), 3.55 (s, 2H); LCMS RtA=0.824 min; [M+H]+=174.1]
70.9% In isopropyl alcohol; Step 1 5-Amino-1-methyl-3-phenylpyrazole (Compound CXXVI) A mixture of 11.0 g. (75.9 mmoles) of benzoylacetonitrile, 3.5 g. (75.9 mmoles) of methylhydrazine and 25 ml. of isopropanol is refluxed under nitrogen for 24 hours, allowed to cool to 20-25 C. and evaporated at reduced pressure. The residual oil is triturated with toluene, and the obtained solid is collected by filtration and vacuum dried to obtain the product as a yellow powder (9.3 g. (70.9%)), m.p. 124-128 C.
In pentan-1-ol; for 2h;Heating / reflux; To a solution of 29 g (0.2 mol) of benzoylacetonitrile in 100 cm3 of n-pentanol were added 14.7 cm3 (0.28 mol) of methylhydrazine and the mixture was heated at reflux for 2 hours. The n-pentanol and the excess methylhydrazine were subsequently distilled off under reduced pressure. A beige solid was obtained, which was taken up in 100 cm3 of heptane at room temperature and filtered off on a sinter funnel. After drying under vacuum at a temperature of 40 C., 27 g of 5-amino-1-methyl-3-phenylpyrazole were obtained in the form of a beige solid, the melting point of which was from 104 to 106 C.
In n-heptane; pentan-1-ol; Preparation Example 3: Synthesis of 4,5-diamino-1-methyl-3-phenylpyrazole dihydrochloride STR12 a) Preparation of 5-amino-1-methyl-3-phenylpyrazole To a solution of 29 g (0.2 mol) of benzoylacetonitrile in 100 cm3 of n-pentanol were added 14.7 cm3 (0.28 mol) of methylhydrazine and the mixture was heated at reflux for 2 hours. The n-pentanol and the excess methylhydrazine were subsequently distilled off under reduced pressure. A beige solid was obtained, which was taken up in 100 cm3 of heptane at room temperature and filtered off on a sinter funnel. After drying under vacuum at a temperature of 40 C., 27 g of 5-amino-1-methyl-3-phenylpyrazole were obtained in the form of a beige solid, the melting point of which was from 104 to 106 C.

  • 10
  • [ 10199-50-5 ]
  • [ 19848-97-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; isopentyl nitrite; In ethanol; water; at 0 - 20℃; for 4h; To a solution of 17.3 g (0.1 mol) of <strong>[10199-50-5]5-amino-1-methyl-3-phenylpyrazole</strong>, obtained in the above step, in 200 cm3 of absolute ethanol were added dropwise 0.5 cm3 of 12 N hydrochloric acid and then 13.5 cm3 of isoamyl nitrite, at 0 C. The solution was subsequently warmed to and left at room temperature for 4 hours. An orange-coloured solid crystallized out. This was filtered off on a sinter funnel and washed with 100 cm3 of isopropyl ether. After drying under vacuum at room temperature, 17 g of 5-amino-1-methyl-4-nitroso-3-phenylpyrazole were obtained in the form of an orange-coloured solid, the melting point of which was from 224 to 226 C.
  • 11
  • 3-dimethylaminomethylene-6-(2-furanyl)oxindole (E isomer) [ No CAS ]
  • 3-dimethylaminomethylene-6-(2-furanyl)oxindole [ No CAS ]
  • [ 10199-50-5 ]
  • 6-(2-furyl)-3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 6-(2-furyl)-3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 12
  • [ 297757-16-5 ]
  • [ 10199-50-5 ]
  • ethyl 3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]
  • ethyl 3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 13
  • 3-dimethylaminomethylene-6-phenyloxindole (E isomer) [ No CAS ]
  • 3-dimethylaminomethylene-6-phenyloxindole (Z isomer) [ No CAS ]
  • [ 10199-50-5 ]
  • 3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino] methylidene}-6-phenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino] methylidene}-6-phenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 14
  • [ 297757-18-7 ]
  • [ 10199-50-5 ]
  • 3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-5-phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-5-phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 15
  • [ 295327-31-0 ]
  • [ 10199-50-5 ]
  • 5-(2-furyl)-3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 5-(2-furyl)-3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 16
  • [ 295327-32-1 ]
  • [ 10199-50-5 ]
  • 3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-5-(3-thienyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl)amino]methylidene}-5-(3-thienyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 17
  • [ 295327-33-2 ]
  • [ 10199-50-5 ]
  • 5-bromo-3-{(E)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl) amino]methylidene}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 5-bromo-3-{(Z)-[(1-methyl-3-phenyl-1H-pyrazol-5-yl) amino]methylidene}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
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