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[ CAS No. 817641-86-4 ] {[proInfo.proName]}

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Chemical Structure| 817641-86-4
Chemical Structure| 817641-86-4
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Product Details of [ 817641-86-4 ]

CAS No. :817641-86-4 MDL No. :MFCD18072639
Formula : C11H19N3 Boiling Point : -
Linear Structure Formula :- InChI Key :VZZTXMPAZZZOFX-UHFFFAOYSA-N
M.W : 193.29 Pubchem ID :52988012
Synonyms :

Calculated chemistry of [ 817641-86-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.73
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.47
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.12
Log Po/w (SILICOS-IT) : 1.53
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.841 mg/ml ; 0.00435 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.713 mg/ml ; 0.00369 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.14
Solubility : 1.39 mg/ml ; 0.00719 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.47

Safety of [ 817641-86-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 817641-86-4 ]

* 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 [ 817641-86-4 ]

[ 817641-86-4 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 817641-86-4 ]
  • [ 7424-91-1 ]
  • 1-tert-Butyl-3-cyclobutyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With acetic acid; at 110℃; for 24h; To 2-tert-butyl-5-cyclobutyl-2H-pyrazol-3-ylamine (5.0 g, 25.9 mmol) in acetic acid (25 mL) was added methyl dimethoxypropionate (7.4 mL, 51.8 mmol), and then the reaction was heated to 110 C. After 24 hr, the reaction mixture was cooled to room temperature, and concentrated to a viscous oil that was diluted with EtOAc. The organic layer was washed with aqueous NaHCO3 and then the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by MPLC using a 45L Biotage column eluding with 20% EtOAc/hexanes. The product-containing fractions were collected and concentrated under reduced pressure, and the resulting solid was washed with hexanes and dried to afford the title compound (2.0 g, 32% yield) as a colorless solid. Rf=0.33 (10% MeOH/CH2Cl2). 400 MHz 1H NMR (CDCl3) d 7.72 (d, J=9.1 Hz, 1H), 6.26 (d, J=9.1 Hz, 1H), 3.68 (dddd, J=8.7, 8.7, 8.7, 8.7 Hz, 1H), 2.46-2.32 (m, 4H), 2.14-1.89 (m, 2H), 1.71 (s, 9H). LRMS m/z (APCI+) 246 (M+1).
32% In acetic acid; at 110℃; for 24h; To 2-TERT-BUTYL-5-CYCLOBUTYL-2H-PYRAZOL-3-YLAMINE (5. 0 g, 25.9 MMOL) in ACOH (25 mL) was added methyl dimethoxypropionate (7.4 mL, 51.8 mmol), and then the reaction was heated to 110 oC. After 24 hr, the reaction mixture was cooled to room temperature, and concentrated to a viscous oil that was treated with EtOAc. The organic layer was washed with aqueous NAHCO3 dried over MGS04, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by MPLC using a 45L BIOTAGE column eluting with 20% EtOAc/hexanes. The product-containing fractions were collected and concentrated under reduced pressure, and the resulting solid was washed with hexanes and dried to afford the title compound (2.0 g, 32% yield) as a colorless SOLID. RF= 0.33 (10% MEOH/CH2CI2) ; 500 MHZ H NMR (CDCI3) d 7.72 (d, J = 9.1 Hz, 1H), 6.26 (d, J = 9.1 Hz, 1H), 3.68 (dddd, J = 8. 7,8. 7,8. 7,8. 7 Hz, 1H), 2.46-2. 32 (m, 4H), 2.14-1. 89 (m, 2H), 1.71 (s, 9H); LRMS m/z (APCI+) 246 (M+1).
  • 2
  • [ 817641-86-4 ]
  • [ 105-45-3 ]
  • [ 817641-87-5 ]
YieldReaction ConditionsOperation in experiment
52% With acetic acid at 105℃; for 19h; 3 Preparation 3; 1-tert-Butyl-3-cyclobutyl-4-methyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one To 2-tert-butyl-5-cyclobutyl-2H-pyrazol-3-ylamine (5.0 g, 25.9 mmol) in acetic acid (25 mL) was added methyl acetoacetate (5.5 mL, 51.8 mmol), and the reaction was heated to 105° C. After 19 hr, the reaction mixture was cooled to room temperature, concentrated to a viscous oil, and then taken up in EtOAc. The reaction mixture was quenched by the slow addition of an aqueous solution of NaHCO3. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by trituration with hexanes to give, after two crops, the title compound (0.7 g, 52% yield) as a colorless solid. 400 MHz 1H NMR (CD3OD) d 6.09 (s, 1H), 3.83 (dddd, J=8.3, 8.3, 8.3, 8.3 Hz, 1H), 2.50-2.27 (m, 7H), 2.08-2.01 (m, 1H), 1.99-1.85 (m, 1H), 1.71 (s, 9H). LRMS m/z (APCI+) 260 (M+1).
  • 3
  • [ 817641-86-4 ]
  • [ 94-02-0 ]
  • 1-tert-butyl-3-cyclobutyl-4-phenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% In acetic acid at 110℃; for 14h; 9 Preparation 9; 1-tert-butyl-3-cyclobutyl-4-phenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one To a stirring solution of crude 2-TEFF-BUTYL-5-CYCLOBUTYL-2H-PYRAZOL-3-YLAMINE (4.0 g, 20.7 MMOL) in ACOH (20 mL) was added 3-oxo-3-phenyl-propionic acid ethyl ester (3.5 g, 20.7 MMOL). The reaction was then heated to 110 oC for 14 hr, at which time the reaction was cooled to room temperature and concentrated under reduced pressure. Purification of the resulting material was accomplished by flash chromatography using a 75 g short BIOTAGEE column, eluting with a gradient of 5%, 10% EtOAc/hexanes. The product-containing fractions were collected and concentrated to give the title compound (1.0 g, 15% yield) as a colorless solid. Rf = 0.31 (20% EtOAc/hexanes); LRMS M/Z (APCI) 322 (M+1); 500 MHZ H NMR (CDCI3) 8 7.46-7. 44 (m, 3H), 7.38-7. 36 (m, 2H), 6.17 (s, 1H), 3.16 (dddd, J = 7.9, 7.9, 79,7. 9 Hz, 1H), 2.17-2. 11 (m, 2H), 1.76 (s, 9H), 1.71-1. 67 (m, 4H); 125 MHZ 13C NMR (CDCI3) 8 163. 1,151. 0,147. 5,141. 8,138. 5,128. 9,128. 4,128. 2,112. 5,110. 6,105. 7, 59.7, 34.2, 29.2, 27.6, 18. 4.
  • 4
  • [ 817641-86-4 ]
  • [ 83643-84-9 ]
  • 1-tert-butyl-3-cyclobutyl-4-trifluoromethyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In acetic acid at 110℃; for 18h; 8 Preparation 8; 1-tert-butyl-3-cyclobutyl-4-trifluoromethyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one To a stirring solution of crude 2-TERT-BUTYL-5-CYCLOBUTYL-2H-PYRAZOL-3-YLAMINE (2.0 g, 10.4 MMOL) in ACOH (10 mL) was added 4,4, 4-trifluoro-3-oxo-butyric acid methyl ester (3.5 g, 20.7 MMOL). The reaction was then heated to 110 oC for 18 hr, at which time the reaction was cooled to room temperature, concentrated under reduced pressure, diluted with EtOAc, and quenched with a saturated aqueous solution of NAHCO3. The organic layer was dried over MGS04, filtered through a fritted funnel, and concentrated under reduced pressure to give the title compound (3.2 g, quantitative yield). This material was used without further purification. LRMS M/Z (APCI) 314 (M+1); 500 MHZ H NMR (CDCI3) 8 6.66 (s, 1H), 3.78 (dddd, J = 8.3, 8.3, 8.3, 8.3 Hz, 1H), 2.49-2. 39 (m, 2H), 2.34-2. 26 (m, 2H), 2.06-1. 85 (m, 2H), 1.75 (s, 9H).
  • 5
  • [ 817641-86-4 ]
  • [ 98349-24-7 ]
  • 1-tert-butyl-5-cyclobutyl-4-(2,4,5-trifluoro-phenyl)-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid; at 110℃; for 14h; To a stirring solution of crude 2-TERT-BUTYL-5-CYCLOBUTYL-2H-PYRAZOL-3-YLAMINE (0.5 g, 2.6 mmol) in ACOH (10 mL) was added 3-OXO-3- (2, 4, 5-trifluoro-phenyl)- PROPIONIC acid ethyl ester (1.3 g, 5.1 MMOL). The reaction mixture was then heated to 110 oC for 14 HR, at which time the reaction was cooled to room temperature and concentrated under reduced pressure. Purification of this material was accomplished by flash chromatography using a 35 g ISCO column, eluting with 20% EtOAc/hexanes. The product-containing fractions were collected and concentrated to give the title compound. LRMS M/Z (APCI) 376 (M+1).
  • 6
  • [ 817641-86-4 ]
  • [ 17838-69-6 ]
  • 1-tert-butyl-3-cyclobutyl-5-phenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% In acetic acid at 110℃; for 18h; 7 Preparation 7; 1-tert-butyl-3-cyclobutyl-5-phenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one To a stirring solution of crude 2-TERT-BUTYL-5-CYCLOBUTYL-2H-PYRAZOL-3-YLAMINE (1.0 g, 5.2 MMOL) in ACOH (5 mL) was added 3-oxo-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 MMOL). The reaction was then heated to 110 oC for 18 hr, at which time the reaction was cooled to room temperature, concentrated under reduced pressure to remove HOAC, diluted with EtOAc, and quenched with a saturated aqueous solution of NAHCO3. The organic layer was dried over MGS04, filtered through a fritted funnel, and concentrated under reduced pressure. Purification of the resulting material was accomplished by flash chromatography with a BIOTAGEE 35L column (A Dynax Corp., Charlottesville, VA), eluting with a gradient of 5%, 10%, 20% ETOAC/HEXANES. The product was collected and concentrated under reduced pressure to give the title compound (15 mg, 9% yield). LRMS M/Z (APCI) 322 (M+1).
  • 7
  • [ 7400-27-3 ]
  • [ 118431-89-3 ]
  • [ 817641-86-4 ]
YieldReaction ConditionsOperation in experiment
80% To a slurry of tert-butylhydrazine hydrochloride (68.0 g, 546.1 mmol) in EtOH (1L) was added NaOH pellets (18.7 g, 468.1 mmol). After 30 min, crude 3-cyclobutyl-3-oxo-propionitrile in EtOH (300 mL) was added. The resulting slurry was heated to 75° C. (oil bath). After 14 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. The resulting slurry was taken up in EtOAc and washed with saturated aqueous NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered through a pad of diatomaceous earth, and concentrated under reduced pressure. Purification of this material was accomplished by recrystallization from 1:1 EtOAc/hexanes to yield, after several crops, the title compound (60.0 g, 80percent yield) as a colorless solid. 400 MHz 1H NMR (CDCl3) d 5.53 (s, 1H), 3.46 (bs, 2H), 3.42 (dddd, J=8.7, 8.7, 8.7, 8.7 Hz, 1H), 2.32-2.23 (m, 2H), 2.14-1.76 (m, 2H), 1.61 (s, 9H). LRMS m/z (APCI+) 194 (M+1).
80% To a slurry of TERT-BUTYLHYDRAZINE HYDROCHLORIDE (68 g, 546 MMOL) in 1 L of EtOH was added sodium hydroxide (18. 7 g, 468.1 MMOL). After 1 hr of stirring, a solution of crude 3-cyclobutyl-3-oxo-propionitrile (390.1 MMOL, in 100 mL of ETOH) was added, and the resulting slurry was heated to reflux. After 12 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. The slurry was diluted with EtOAc and then washed with a saturated solution of NAHCO3. The organic layer was dried over MGS04, filtered through a fritted funnel, and concentrated under reduced pressure. The product was isolated by trituration with 25percent EtOAc/hexanes. After several trituration cycles, the title compound (60 g, 80percent yield) was collected as a colorless solid, which was used without further purification. LRMS m/z (APCI) 194 (M+1).
In ethanol; for 20h;Reflux; A round bottom flask was charged with 3-cyclobutyl-3-oxo-propionitrile (CK01, 12.3 g, 0.1 mol), tert-butylhydrazine hydrochloride ([7400-27-3], 13.5 g, 0.11 mol) and EtOH (150 mL). The reaction mixture was refluxed for 20 hours and cooled down to RT. Half of the solvent was removed by concentration in vacuo, and the mixture was cooled in an ice bath. The formed precipitate was collected by filtration and washed successively with diethyl ether and n-pentane. The filtrate was allowed to stand for 1 hour, and the formed precipitate was again collected by filtration and washed with diethyl ether and w-pentane. The combined solids were stirred in ethyl acetate and a saturated solution of NaHCO3. The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the titled compound.
for 20h;Reflux; 11484] A round bottom flask was charged with 3-cyclobu- tyl-3-oxo-propionitrile (CKO1, 12.3 g, 0.1 mol), tert-butylhydrazine hydrochloride ([7400-27-3], 13.5 g, 0.11 mol) and EtOH (150 mE). The reaction mixture was refluxed for 20 hours and cooled down to RT. Half of the solvent was removed by concentration in vacuo, and the mixture was cooled in an ice bath. The formed precipitate was collected by filtration and washed successively with diethyl ether and n-pentane. The filtrate was allowed to stand for 1 hour, and the formed precipitate was again collected by filtration and washed with diethyl ether and n-pentane. The combined solids were stirred in ethyl acetate and a saturated solution of NaHCO3. The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the titled compound.

  • 8
  • [ 817641-86-4 ]
  • ethyl 1-tert-butyl-3-cyclobutyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 20 h / 20 °C 2: 24 h / 185 - 190 °C / Sealed tube
  • 9
  • [ 817641-86-4 ]
  • ethyl 1-tert-butyl-3-cyclobutyl-4-[(trifluoromethanesulfonyl)oxy]-1H-pyrazolo[3,4-b]pyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 20 h / 20 °C 2: 24 h / 185 - 190 °C / Sealed tube 3: pyridine / acetonitrile / 20 h / 20 - 25 °C
Multi-step reaction with 3 steps 1: ethanol / 20 h / 20 °C 2: 24 h / 185 - 190 °C / Sealed tube 3: pyridine / acetonitrile / 20 h / 20 - 25 °C
  • 10
  • [ 817641-86-4 ]
  • [ 762-21-0 ]
  • diethyl 2-[(1-tert-butyl-3-cyclobutyl-1H-pyrazol-5-yl)amino]but-2-enedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20℃; for 20h; 1 Step 1: diethyl 2-[(1-tert-butyl-3-cyclobutyl-1H-pyrazol-5-yl)amino]but-2-enedioate In an amber round bottom flask, diethyl acetylenedicarboxylate ([762-21-0], 14.8 mL, 87 mmol) was added to a suspension of AMP94 (15.2 g, 78.8 mmol) in ethanol (200 mL). The reaction mixture was stirred at room temperature for 20 hours, and the mixture was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (heptane/dichloromethane 100/0 to 0/100) to give the titled compound.
In ethanol at 20℃; for 20h; 1 Step 1: diethyl 2-[(1-tert-butyl-3-cyclobutyl-1H-pyrazol-5-yl)amino]but-2-enedioate In an amber round bottom flask, diethyl acetylenedicarboxylate ([762-21-0], 14.8 mL, 87 mmol) was added to a suspension of AMP94 (15.2 g, 78.8 mmol) in ethanol (200 mL). The reaction mixture was stirred at room temperature for 20 hours, and the mixture was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (heptane/dichloromethane 100/0 to 0/100) to give the titled compound.
  • 11
  • [ 14924-53-9 ]
  • [ 817641-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 °C 2.1: ethanol / 20 h / Reflux
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