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Product Details of [ 208519-09-9 ]

CAS No. :208519-09-9 MDL No. :MFCD11504907
Formula : C9H8ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :HLKDVENNWRMMOS-UHFFFAOYSA-N
M.W : 193.63 Pubchem ID :3820802
Synonyms :

Calculated chemistry of [ 208519-09-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.44
TPSA : 54.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.212 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.222 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0188 mg/ml ; 0.0000971 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 208519-09-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 208519-09-9 ]

* 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 [ 208519-09-9 ]

[ 208519-09-9 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 141-97-9 ]
  • [ 208519-09-9 ]
  • [ 77493-74-4 ]
YieldReaction ConditionsOperation in experiment
69% In acetic acid for 20h; Heating;
  • 2
  • [ 94-02-0 ]
  • [ 208519-09-9 ]
  • [ 77493-75-5 ]
YieldReaction ConditionsOperation in experiment
73% In acetic acid for 20h; Heating;
45% With acetic acid at 150℃; for 2h; 1.3 General procedure for the one potsynthesis of pyrazolopyrimidones General procedure: Pyrazolopyrimidinones5, 6. 10, 13, 14, 15 were prepared as per the following literature procedure.1A microwave tube was charged with ketonitrile (0.9 mmol), methanol (1 mL), andhydrazine monohydrate (1.2 mmol) and subjected to microwave irradiation (100 W,150 °C) for 5 minutes. Subsequently, to this solution was added ketoester (0.9mmol) and acetic acid (0.5 mmol), and the mixture was subjected to microwaveirradiation (100 W, 150 °C) for 2 hours. Volatiles were removed underreduced pressure. The mixturewas purified by either trituration with cold methanol or ethyl acetate, or byusing column chromatography.
0.131 g With acetic acid In methanol at 150℃; for 2h; Microwave irradiation; 1.3. General procedure of one pot synthesis of pyrazolopyrimidones General procedure: A microwave tube was charged with ketonitrile (0.9 mmol), methanol (1 mL), and hydrazine monohydrate (1.2 mmol) and subjected to microwave irradiation (100 W, 150 °C) for 5 minutes. Subsequently, to this solution was added ketoester (0.9 mmol) and acetic acid (0.5 mmol), and the mixture was subjected to microwave irradiation (100 W, 150 °C) for 2 hours. Volatiles were removed under reduced pressure. The mixture was purified by either trituration with cold methanol or ethyl acetate, or by using column chromatography
  • 3
  • [ 21667-62-9 ]
  • [ 208519-09-9 ]
YieldReaction ConditionsOperation in experiment
94% With hydrazine hydrate; In methanol; at 150℃; for 0.0833333h;Microwave irradiation; General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.
70% With hydrazine; In ethanol; at 80℃; for 15h; To a stirring solution of 3- (3-clilorophenyl)-3-oxo-propionitrile (2 g, 11.1 mmol) in absolute ethanol (20 mL) was added hydrazine hydrate (3.24 mL, 67 mmol). The reaction mixture was stirred at 80C for 15 h, cooled to room temperature, concentrated in vacuo, and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2C12 as eluent provided 1.53 g (70%) of 5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine as a green solid. 1H NMR (d6-DMSO) No.: 11. 6 and 11. 9 (2 broad s, 1H, NH+tautomer), 7. 69 (s, 1H), 7.60 (d, 1H), 7. 38 (t, 1H), 7.29 (d, 1H), 5.77 (broad s, 1H), 4.98 (broad s, 2H, NH2). To a stirring solution of 5- (3-chloro-phenyl)-2H-pyrazol-3-ylamine (1.53 g, 7.9 mmol) in THF (32 mL) was added N-bromosuccinimide (1.55 g, 8.7 mmol). The reaction mixture was stirred for 5 h at room temperature, then absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CHzClz as eluent provided 1.73 g (80%) of 4-bromo-5- (3- chloro-phenyl)-2H-pyrazol-3-ylamine as a brown solid. 1H NMR (d6-DMSO) No.: 12.2 and 12.4 (2 broad s, 1H, NH+tautomer), 7.77 (s, 1H), 7.73 (broad s, 1H), 7.48 (broad s, 1H), 7.43 (broad s, 1H), 5.30 (broad s, 1H, NH), 4.82 (broad s, 1H, NH) ; HPLC/MS m/z : 272 [MH3+. To a stirring solution of 4-bromo-5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine (50 mg, 0. 183 mmol) in dioxane (1 mL) was added benzoyl isothiocyanate (27 JIL, 0.202 mmol). The reaction mixture was stirred overnight at 90C, cooled at room temperature, and partitioned between ethyl acetate and sodium bicarbonate. The organic layer was isolated and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2C12 as eluent provided 10.8mg (17%) ofN [3- (3-chloro-phenyl)-lH-pyrazolo [3, 4-d] thiazol-5-yl]- benzamide as a white solid NMR (d6-DMSO) d : 13.70 and 13.72 (2 broad s, 1H, NH+tautomer), 12.9 (broad s, 1H, NH), 8.12 (d, 2H), 7.81 and 7. 85 (2 broad s, 1H, tautomers), 7.65-7. 74 (m, 2H), 7.54-7. 62 (m, 3H), 7.45 (m, 1H) ; HPLC/MS m/z : 355 [MH] +.
  • 4
  • [ 208519-09-9 ]
  • [ 3788-94-1 ]
  • [ 203587-56-8 ]
YieldReaction ConditionsOperation in experiment
90% In ethanol for 0.5h; Heating;
  • 5
  • [ 25177-85-9 ]
  • [ 208519-09-9 ]
  • N-[5-(3-chlorophenyl)-1H-pyrazol-3-yl]-2-indanecarboxamide [ No CAS ]
  • 6
  • [ 208519-09-9 ]
  • [ 1885-14-9 ]
  • [5-(3-chloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-carbamic acid phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 2h;
  • 7
  • [ 2905-65-9 ]
  • [ 208519-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 - 20 °C 2.1: hydrazine monohydrate / ethanol / 5 h / Heating
Multi-step reaction with 2 steps 1: 70 percent / NaH / toluene / 40 h / 60 - 70 °C 2: 67 percent / H2NNH22*H2O / ethanol / 2 h / Heating
  • 8
  • [ 208519-09-9 ]
  • 4-(2-methanesulfonylamino-phenyl)-piperazine-1-carboxylic acid [5-(3-chloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 2 h / 20 °C 2: 30 mg / triethylamine / CHCl3 / 1 h / Heating
  • 9
  • [ 208519-09-9 ]
  • [ 77493-90-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 69 percent / acetic acid / 20 h / Heating 2: 84 percent / N,N-dimethylaniline, POCl3 / 3 h / Heating
  • 10
  • [ 208519-09-9 ]
  • [ 77493-91-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / acetic acid / 20 h / Heating 2: 50 percent / N,N-dimethylaniline, POCl3 / 3 h / Heating
  • 11
  • [ 208519-09-9 ]
  • [ 860477-80-1 ]
YieldReaction ConditionsOperation in experiment
80% With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 5h; 1 To a stirring solution of 3- (3-clilorophenyl)-3-oxo-propionitrile (2 g, 11.1 mmol) in absolute ethanol (20 mL) was added hydrazine hydrate (3.24 mL, 67 mmol). The reaction mixture was stirred at 80°C for 15 h, cooled to room temperature, concentrated in vacuo, and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2C12 as eluent provided 1.53 g (70%) of 5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine as a green solid. 1H NMR (d6-DMSO) No.: 11. 6 and 11. 9 (2 broad s, 1H, NH+tautomer), 7. 69 (s, 1H), 7.60 (d, 1H), 7. 38 (t, 1H), 7.29 (d, 1H), 5.77 (broad s, 1H), 4.98 (broad s, 2H, NH2). To a stirring solution of 5- (3-chloro-phenyl)-2H-pyrazol-3-ylamine (1.53 g, 7.9 mmol) in THF (32 mL) was added N-bromosuccinimide (1.55 g, 8.7 mmol). The reaction mixture was stirred for 5 h at room temperature, then absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CHzClz as eluent provided 1.73 g (80%) of 4-bromo-5- (3- chloro-phenyl)-2H-pyrazol-3-ylamine as a brown solid. 1H NMR (d6-DMSO) No.: 12.2 and 12.4 (2 broad s, 1H, NH+tautomer), 7.77 (s, 1H), 7.73 (broad s, 1H), 7.48 (broad s, 1H), 7.43 (broad s, 1H), 5.30 (broad s, 1H, NH), 4.82 (broad s, 1H, NH) ; HPLC/MS m/z : 272 [MH3+. To a stirring solution of 4-bromo-5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine (50 mg, 0. 183 mmol) in dioxane (1 mL) was added benzoyl isothiocyanate (27 JIL, 0.202 mmol). The reaction mixture was stirred overnight at 90°C, cooled at room temperature, and partitioned between ethyl acetate and sodium bicarbonate. The organic layer was isolated and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2C12 as eluent provided 10.8mg (17%) ofN [3- (3-chloro-phenyl)-lH-pyrazolo [3, 4-d] thiazol-5-yl]- benzamide as a white solid NMR (d6-DMSO) d : 13.70 and 13.72 (2 broad s, 1H, NH+tautomer), 12.9 (broad s, 1H, NH), 8.12 (d, 2H), 7.81 and 7. 85 (2 broad s, 1H, tautomers), 7.65-7. 74 (m, 2H), 7.54-7. 62 (m, 3H), 7.45 (m, 1H) ; HPLC/MS m/z : 355 [MH] +.
  • 12
  • [ 68-11-1 ]
  • [ 208519-09-9 ]
  • [ 1141402-10-9 ]
YieldReaction ConditionsOperation in experiment
98% In toluene at 110℃; Inert atmosphere;
  • 13
  • [ 141-97-9 ]
  • [ 208519-09-9 ]
  • [ 332899-44-2 ]
YieldReaction ConditionsOperation in experiment
88% In o-xylene at 155 - 160℃; for 20h; 2-(3-Chlorophenyl)-5-methylpyrazolofl,5-aJpyrimidin-7-ol. ; A suspension of 3-(3- chlorophenyl)-lH-pyrazol-5 -amine (10 g, 51.6 mmol) and ethyl 3-oxobutanoate (26.3 ml, 207 mmol) in o-xylene (200 mL) was heated at reflux (oil bath temp: 155-160 °C) for 20 h. Note: The reaction turned clear solution between 60-70 °C and solids started crashing out at 130 °C. Then, cooled, diluted with hexanes (100 mL), filtered, washed with hexanes (100 mL) and dried to afford 2-(3-chlorophenyl)-5- methylpyrazolo[l,5-a]pyrimidin-7-ol (1 1.8 g, 45.4 mmol, 88 % yield) as off-white solid. 'H NMR (400MHZ, DMSO-d6) δ: 12.46 (s, 1H), 8.05 (s, 1H), 8.00 - 7.95 (m, 1H), 7.56 - 7.45 (m, 2H), 6.70 (s, 1H), 5.64 (s, 1H), 2.33 (s, 3H). LCMS (M+H) calcd for Ci3HnClNnO: 260.06; found: 260.1.
  • 14
  • [ 208519-09-9 ]
  • [ 1364597-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2: trichlorophosphate / 2.5 h / Reflux
  • 15
  • [ 208519-09-9 ]
  • [ 1364597-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C
  • 16
  • [ 208519-09-9 ]
  • [ 1364597-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
  • 17
  • [ 208519-09-9 ]
  • [ 1364597-58-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 3.5 h / -45 - -15 °C
  • 18
  • [ 208519-09-9 ]
  • [ 1364597-62-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 3.5 h / -45 - -15 °C 6.1: perchloric acid / dichloromethane / 16 h / 20 °C
  • 19
  • [ 208519-09-9 ]
  • [ 1364597-66-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 3.5 h / -45 - -15 °C 6.1: perchloric acid / dichloromethane / 16 h / 20 °C 7.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 125 °C / Microwave irradiation
  • 20
  • [ 208519-09-9 ]
  • [ 1364597-66-9 ]
  • [ 1364597-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: perchloric acid / dichloromethane / 5 h / 20 °C 5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 115 °C / Microwave irradiation 6.1: Chiralpak AD-H / carbon dioxide; methanol / 35 °C / 112511 Torr / Resolution of racemate
  • 21
  • [ 208519-09-9 ]
  • [ 1364597-70-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: perchloric acid / dichloromethane / 5 h / 20 °C 5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 115 °C / Microwave irradiation 6.1: Chiralpak AD-H / carbon dioxide; methanol / 35 °C / 112511 Torr / Resolution of racemate 7.1: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / N,N-dimethyl-formamide / 0.5 h / 130 °C / Microwave irradiation
Multi-step reaction with 8 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 3.5 h / -45 - -15 °C 6.1: perchloric acid / dichloromethane / 16 h / 20 °C 7.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 125 °C / Microwave irradiation 8.1: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / N,N-dimethyl-formamide / 0.5 h / 130 °C / Microwave irradiation
  • 22
  • [ 208519-09-9 ]
  • [ 1364592-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: perchloric acid / dichloromethane / 5 h / 20 °C 5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 115 °C / Microwave irradiation 6.1: Chiralpak AD-H / carbon dioxide; methanol / 35 °C / 112511 Torr / Resolution of racemate 7.1: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / N,N-dimethyl-formamide / 0.5 h / 130 °C / Microwave irradiation 8.1: sodium hydroxide; water / 1,4-dioxane / 2 h / 50 °C
Multi-step reaction with 9 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 3.5 h / -45 - -15 °C 6.1: perchloric acid / dichloromethane / 16 h / 20 °C 7.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 125 °C / Microwave irradiation 8.1: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / N,N-dimethyl-formamide / 0.5 h / 130 °C / Microwave irradiation 9.1: sodium hydroxide; water / 1,4-dioxane / 2 h / 50 °C
  • 23
  • [ 208519-09-9 ]
  • [ 1364597-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: perchloric acid / dichloromethane / 5 h / 20 °C
  • 24
  • [ 208519-09-9 ]
  • [ 1364597-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / o-xylene / 2 h / Reflux 2.1: trichlorophosphate / 2.5 h / Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C 3.2: 2.5 h / -78 °C 4.1: perchloric acid / dichloromethane / 5 h / 20 °C 5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.75 h / 115 °C / Microwave irradiation
  • 25
  • [ 208519-09-9 ]
  • [ 1364598-94-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: copper(I) bromide / tetrahydrofuran / 1.08 h 4.2: 1 h
  • 26
  • [ 208519-09-9 ]
  • [ 1364598-97-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: copper(I) bromide / tetrahydrofuran / 1.08 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.67 h / -35 °C 5.2: 0.5 h
  • 27
  • [ 208519-09-9 ]
  • [ 1364599-00-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: copper(I) bromide / tetrahydrofuran / 1.08 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.67 h / -35 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 2 h / 20 °C
  • 28
  • [ 208519-09-9 ]
  • [ 1364594-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: copper(I) bromide / tetrahydrofuran / 1.08 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.67 h / -35 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 2 h / 20 °C 7.1: sodium hydroxide; methanol / 16 h / 60 °C
  • 29
  • [ 208519-09-9 ]
  • 2-(3-chlorophenyl)-7-isobutyl-5-methylpyrazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 6.08 h / 20 °C 4.2: 1 h
  • 30
  • [ 208519-09-9 ]
  • [ 1364599-13-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.25 h 4.2: 1 h
  • 31
  • [ 208519-09-9 ]
  • [ 1364599-16-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.25 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 1 h / -35 - -15 °C 5.2: 0.5 h
  • 32
  • [ 208519-09-9 ]
  • [ 1364599-19-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.25 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 1 h / -35 - -15 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 2 h / 20 °C
  • 33
  • [ 208519-09-9 ]
  • [ 1364594-90-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.25 h 4.2: 1 h 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 1 h / -35 - -15 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 2 h / 20 °C 7.1: sodium hydroxide; methanol / 3 h / Reflux
  • 34
  • [ 208519-09-9 ]
  • [ 1364599-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.67 h / 20 °C 4.2: 20 °C
  • 35
  • [ 208519-09-9 ]
  • [ 1364599-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.67 h / 20 °C 4.2: 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.58 h / -35 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 1.5 h / 20 °C / Sealed reaction
  • 36
  • [ 208519-09-9 ]
  • [ 1364599-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.67 h / 20 °C 4.2: 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.58 h / -35 °C 5.2: 0.5 h
  • 37
  • [ 208519-09-9 ]
  • [ 1364594-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 2.67 h / 20 °C 4.2: 20 °C 5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene; tetrahydrofuran / 0.58 h / -35 °C 5.2: 0.5 h 6.1: perchloric acid / dichloromethane / 1.5 h / 20 °C / Sealed reaction 7.1: sodium hydroxide; methanol / Reflux
  • 38
  • [ 208519-09-9 ]
  • 2-(3-chlorophenyl)-7-cyclohexyl-5-methylpyrazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: o-xylene / 20 h / 155 - 160 °C 2.1: bromine / dichloromethane; methanol / 2.33 h 3.1: N,N-diethylaniline; trichlorophosphate / 16 h / 120 °C 4.1: lithium chloride / copper(I) bromide / tetrahydrofuran / 1.67 h / 20 °C 4.2: 1 h
  • 39
  • [ 10420-33-4 ]
  • [ 208519-09-9 ]
  • [ 1364597-43-2 ]
YieldReaction ConditionsOperation in experiment
99% toluene-4-sulfonic acid; In o-xylene; for 2h;Reflux; Methyl 2-(2-(3-chlorophenyl)-7-hydroxy-5-methylpyrazolo [ 1 ,5-a] pyrimidin-6- yl)acetate.; To a solution of 3-(3-chlorophenyl)-lH-pyrazol-5-amine (23 g, 119 mmol), <strong>[10420-33-4]dimethyl 2-acetylsuccinate</strong> (22.35 g, 1 19 mmol) in o-Xylene (200 mL) was added -toluenesulfonic acid monohydrate (100 mg, 0.526 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 2 h. The solid was filtered and washed with hexanes to afford (39 g, 99%) of the title compound. XH NMR (500MHz, METHANOL-d4) delta 8.14 - 7.95 (m, 1H), 7.93 - 7.79 (m, 1H), 7.51 - 7.27 (m, 2H), 6.62 - 6.35 (m, 1H), 3.72 (s, 3H), 3.67 (s, 2H), 2.39 (s, 3H).
  • 40
  • [ 420-04-2 ]
  • [ 208519-09-9 ]
  • [ 122-51-0 ]
  • 4-amino-7-(3-chlorophenyl)pyrazolo[1,5-a][1,3,5]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In methanol at 150℃; for 0.416667h; Microwave irradiation; regioselective reaction; General method for the synthesis of 5-aza-9-deaza-adenines 6. General procedure: A mixture of 5-aminopyrazole 4 (1.3 mmol), cyanamide (63.3 mg, 1.5 mmol) and triethylorthoformate (0.3 mL, 2.3 mmol) in MeOH (2 mL) was irradiated in a 10mL seamless pressure vial using a CEM Discover microwave synthesizer operating at maximal microwave power up to 150 W at 150 °C for 25 min. After cooling, the precipitated product 6 was filtered, washed with cold MeOH and dried under vacuum.
  • 41
  • [ 614-16-4 ]
  • [ 208519-09-9 ]
  • 3-(3-chlorophenyl)-4-cyclopropyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 16 h / 90 °C 2: sodium nitrite / acetic acid / 0.17 h / 20 °C
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 16 h / 90 °C 2: sodium nitrite; acetic acid / 0.17 h
  • 42
  • [ 614-16-4 ]
  • [ 208519-09-9 ]
  • [ 1489-69-6 ]
  • C22H17ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h; 3-(3-Chlorophenyl)-4-cyclopropyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (12); Typical Procedure 3-(3-Chlorophenyl)-1H-pyrazol-5-amine (400 mg, 2.07 mmol, 1equiv), 3-oxo-3-phenylpropanenitrile (300 mg, 2.07 mmol, 1 equiv), cyclopropanecarbaldehyde (154 μL, 2.07 mmol, 1 equiv), and Et3N (576 μL, 4.13 mmol, 2 equiv) were stirred in DMF (2.1 mL, 1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (positive N2 (g) pressure can also be used). NaNO2 (428 mg, 6.20 mmol, 3 equiv) and AcOH (1.56 mL, 273 mmol, 134 equiv) were added to the crude material, and the mixture was stirred for 10 min. The volatiles were removed under reduced pressure, and the crude mixture was subjected to column chromatography (silica gel, 0-30% EtOAc/hexanes gradient) to give the product (500 mg, 1.35 mmol, 65%) as an off-white solid; Rf = 0.41 (30% EtOAc/hexanes).
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h;
  • 43
  • [ 1246765-49-0 ]
  • [ 208519-09-9 ]
  • [ 4640-66-8 ]
  • C23H16Cl2F2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h; Typical Reaction Procedure General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.
  • 44
  • [ 59997-51-2 ]
  • [ 208519-09-9 ]
  • C20H19ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 16 h / 90 °C 2: sodium nitrite / acetic acid / 0.17 h / 20 °C
  • 45
  • [ 59997-51-2 ]
  • [ 208519-09-9 ]
  • [ 1489-69-6 ]
  • C20H21ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h; Typical Reaction Procedure General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.
  • 46
  • [ 208519-09-9 ]
  • [ 118431-89-3 ]
  • C20H17ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 16 h / 90 °C 2: sodium nitrite / acetic acid / 0.17 h / 20 °C
  • 47
  • [ 208519-09-9 ]
  • [ 118431-89-3 ]
  • [ 1489-69-6 ]
  • C20H19ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h; Typical Reaction Procedure General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.
  • 48
  • [ 96798-17-3 ]
  • [ 406-87-1 ]
  • [ 208519-09-9 ]
  • C21H22ClF3N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h; Typical Reaction Procedure General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.
  • 52
  • [ 208519-09-9 ]
  • [ 10420-33-4 ]
  • [ 1364597-43-2 ]
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