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[ CAS No. 184097-88-9 ] {[proInfo.proName]}

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Chemical Structure| 184097-88-9
Chemical Structure| 184097-88-9
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Product Details of [ 184097-88-9 ]

CAS No. :184097-88-9 MDL No. :MFCD08059554
Formula : C9H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :GDTZRPGWZFOSSY-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :21669713
Synonyms :

Calculated chemistry of [ 184097-88-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.97
TPSA : 43.84 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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 1.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.638 mg/ml ; 0.00401 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.42 mg/ml ; 0.00893 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.56
Solubility : 0.444 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 184097-88-9 ]

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

Application In Synthesis of [ 184097-88-9 ]

* 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 [ 184097-88-9 ]

[ 184097-88-9 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 25688-18-0 ]
  • [ 184097-88-9 ]
YieldReaction ConditionsOperation in experiment
92% With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 1h; Reflux; 8.3 3) Synthesis of Compound Represented by Formula 8-c 20.0 g (106 mmol) of the compound represented by the formula 8-b], palladium / carbon catalyst (10%) obtained from the reaction scheme 48,26.5 g (529 mmol) of hydrazine monohydrate,200 ml of ethanol was added and the mixture was refluxed for 1 hour. After completion of the reaction, the reaction mixture was hot-filtered using silica gel / celite and the solvent was concentrated under reduced pressure. (15.5 g, 92% yield)
91% With hydrogen In ethyl acetate at 20℃; for 17h; 110.B A mixture of 110A (0.95 g, 5.0 mmol) and 10% palladium on charcoal (0.27 g) in 10 mL of ethyl acetate was stirred at rt under an atmosphere of hydrogen for 17 h. The resulting mixture was filtered through a pad of celite and the resulting filtrate was concentrated in vacuo to afford 0.73 g (91%) of 110B as a pale yellow oil. LCMS (M+H+) = 160. 1. HPLC Ret. time: 0.74 min.
68% With hydrazine hydrate In ethanol for 1h; Heating;
  • 2
  • [ 544-92-3 ]
  • [ 151-50-8 ]
  • [ 184097-88-9 ]
  • [ 25699-82-5 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 3-(1H-pyrazol-1-yl)aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: copper(I) cyanide; potassium cyanide In water at 60℃; for 0.333333h;
  • 3
  • [ 108-77-0 ]
  • [ 184097-88-9 ]
  • 6-chloro-N,N'-bis(3-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 26h;
  • 4
  • [ 619-27-2 ]
  • [ 184097-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 84 percent / ethanol / 1 h / Heating 2: 68 percent / hydrazine hydrate / Pd/C / ethanol / 1 h / Heating
  • 5
  • [ 184097-88-9 ]
  • 2,4,6-tris(3-(1H-pyrazol-1-yl)phenyl)-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaNO2; HCl / H2O / 0 - 5 °C 1.2: 64 percent / CuCN / H2O / 0.33 h / 60 °C 2.1: 26 percent / piperidine; (CF3COO)3Y / 24 h / 200 °C
  • 6
  • [ 288-13-1 ]
  • [ 6311-60-0 ]
  • [ 1013655-28-1 ]
  • [ 184097-88-9 ]
  • 7
  • [ 12107-56-1 ]
  • [ 1079-66-9 ]
  • [ 184097-88-9 ]
  • [ 1033630-77-1 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine In hexane; toluene under Ar atm. soln. ClPPh2 in toluene was added dropwise to soln. amine and Et3N in toluene-hexane at room temp. and stirred for 10 h, added to suspn. Pd complex in toluene and heated to reflux for 4 h; soln. was filtered and concd. in vacuo, residue was dissolved in acetoneand cooled to -20°C; elem. anal.;
  • 8
  • [ 98-88-4 ]
  • [ 184097-88-9 ]
  • [ 1152493-51-0 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine In ethyl acetate at 0 - 20℃; for 4h;
  • 9
  • [ 1372890-32-8 ]
  • [ 184097-88-9 ]
  • [ 1372890-53-3 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate; 3-(1H-pyrazol-1-yl)aniline In methanol at 20℃; for 0.5h; Stage #2: With sodium cyanoborohydride; acetic acid In methanol at 20℃; 75.1 Example 752-(2-{(cyclopropylcarbonyl)[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-N-hydroxy-1-oxo-1,2-dihydroisoquinoline-7-carboxamide; Compound I-45 Step 1: methyl 1-oxo-2-(2-[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1,2-dihydroisoquinoline-7-carboxylateA solution of methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.15 g, 0.61 mmol) and 3-(1H-pyrazol-1-yl)aniline (0.15 g, 0.92 mmol) in methanol (2 mL) was stirred at rt for 30 mins. Then acetic acid (3.5 μL, 0.06 mmol) and sodium cyanoborohydride (96 mg, 1.5 mmol) was added and the reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (20% to 70% EtOAc/hexanes) to afford methyl 1-oxo-2-(2-[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.14 g, 59%). LC-MS: (FA) ES+389.
  • 10
  • [ 1439908-36-7 ]
  • [ 184097-88-9 ]
  • [ 1439909-30-4 ]
YieldReaction ConditionsOperation in experiment
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; caesium carbonate; bis(dibenzylideneacetone)-palladium(0) In toluene at 105℃; Inert atmosphere; 34 The mixture of tert-butyl (1S,2S)-2-(4-chloro-5-cyanopyrimidin-2-ylamino)-3,3-difluorocyclohexylcarbamate (A17, Example 14) (70 mg, 0.18 mmol), 3-(lH-pyrazol-l- yl)aniline (58 mg, 0.36 mmol), fine powder Cs2C03 (180 mg, 0.54 mmol), Q-Phos (28 mg, 0.04 mmol) and Pd(dba)2 (23 mg, 0.04 mmol) in 15 mL toluene was degassed using argon stream and stirred at 105°C under argon atmosphere for overnight. It was diluted with 100 mL EtOAc, filtered through celite, concentrated in vacuo and subjected to flash column to isolate tert-butyl (( 1 S,2S)-2-((4-((3 -( 1 H-pyrazol- 1 -yl)phenyl)amino)-5-cyanopyrimidin-2-yl)amino)-3 ,3- difluorocyclohexyl)carbamate.It was treated with 5 mL TFA and 1 mL concentrate H2S04 at 80°C for 1 h. It was cooled to RT. To it was added 5 mL water. The mixture was stirred, cooled, filtered and subjected to reverse phase preparative HPLC to isolate the title compound (21 mg). MS found for C20H22F2N8O as (M+H)+ 429.4. UV: λ=244 nm.
  • 11
  • 2-chloro-5-fluoro-N-[(3S)-1-methylpiperidin-3-yl]methyl}pyrimidin-4-amine [ No CAS ]
  • [ 184097-88-9 ]
  • 5-fluoro-N4-[(3S)-1-methylpiperidin-3-yl]methyl}-N2-[3-(1H-pyrazol-1-yl)phenyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride In ethyl acetate; isopropyl alcohol at 120℃; for 9h; 23 5-Fluoro-N4-[(3S)-1-methylpiperidin-3-yl]methyl}-N2-[3-(1H-pyrazol-1-yl)phenyl]pyrimidine-2,4-diamine (14d) Compound 14d was prepared from compound 13 in 86% yield as a colorless solid, using a similar approach to that described for 14a. 1H NMR (DMSO-d6) δ 0.82-0.97 (1H, m), 1.31-1.45 (1H, m), 1.53-1.68 (3H, m), 1.74-1.97 (2H, m), 2.08 (3H, s), 2.50-2.71 (2H, m), 3.21-3.41 (2H, m), 6.52 (1H, dd, J = 2.4, 1.6 Hz), 7.24-7.34 (2H, m), 7.48-7.59 (2H, m), 7.71 (1H, d, J = 1.6 Hz), 7.88 (1H, d, J = 4.0 Hz), 8.34 (1H, d, J = 2.4 Hz), 8.44 (1H, dd, J = 1.6, 1.6 Hz), 9.24 (1H, s); MS (ESI) m/z 382 [M+H]+; HRMS (ESI) calcd for C20H24FN7 [M+H]+: 382.2155, found: 382.2148.
  • 12
  • [ 402-67-5 ]
  • [ 184097-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 17 h / 100 °C 2: hydrogen / palladium 10% on activated carbon / ethyl acetate / 17 h / 20 °C
  • 13
  • [ 288-13-1 ]
  • [ 591-19-5 ]
  • [ 184097-88-9 ]
YieldReaction ConditionsOperation in experiment
89% With D-galacturonic acid; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 80 - 100℃; Inert atmosphere; Green chemistry; General Procedure for Catalytic Experiments General procedure: To a 10 mL vial was charged with aryl halide (0.8 mmol), N-containing heterocycle (1.0 mmol), CuBr (0.04 mmol), GalA (0.08mmol), K2CO3 (2.4 mmol), and 50% aq DMSO. The flask wasevacuated and backfilled with argon three times, and the reaction mixture was stirred at appropriate temperature under oil bath for the indicated time. After the complete consumption of aryl halide monitored by TLC, the mixture was then cooled to ambient temperature (if the product was acidic, the mixture was acidified), diluted with ethyl acetate (5 mL), filtered via aCelite pad, and washed with ethyl acetate (10-20 mL). The organic layer was separated by the separating funnel, which was washed successively with water (2 × 10 mL) and brine (2 ×10 mL). The organic layer was dried over anhydrous MgSO4 and concentrated by reduced pressure in a rotary evaporator, which was then purified by column chromatography on silica gel to provide the desired products.
  • 14
  • [ 4295-06-1 ]
  • [ 184097-88-9 ]
  • N-[3-(1H-pyrazol-1-yl)phenyl]-2-methylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.95% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
91.95% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
  • 15
  • [ 86-98-6 ]
  • [ 184097-88-9 ]
  • N-[3-(1H-pyrazol-1-yl)phenyl]-7-chloroquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.6% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
85.6% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
  • 16
  • [ 75896-68-3 ]
  • [ 184097-88-9 ]
  • N-[3-(1H-pyrazol-1-yl)phenyl]-7-methoxy-2-methylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.88% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
91.88% With indium(III) chloride In acetonitrile at 110 - 170℃; Microwave irradiation; 5 General procedure for synthesis of biarylquinoline derivatives General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110°C to 170°C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
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