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[ CAS No. 936353-84-3 ] {[proInfo.proName]}

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Chemical Structure| 936353-84-3
Chemical Structure| 936353-84-3
Structure of 936353-84-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 936353-84-3 ]

CAS No. :936353-84-3 MDL No. :MFCD09907981
Formula : C10H16BN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YGZOCDXCJWHNQN-UHFFFAOYSA-N
M.W : 221.06 Pubchem ID :53398055
Synonyms :

Calculated chemistry of [ 936353-84-3 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 70.32
TPSA : 59.83 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.02
Log Po/w (WLOGP) : -2.25
Log Po/w (MLOGP) : -0.71
Log Po/w (SILICOS-IT) : -1.64
Consensus Log Po/w : -0.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.37
Solubility : 9.46 mg/ml ; 0.0428 mol/l
Class : Very soluble
Log S (Ali) : -0.83
Solubility : 32.8 mg/ml ; 0.148 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.09
Solubility : 17.9 mg/ml ; 0.0809 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.54

Safety of [ 936353-84-3 ]

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

Application In Synthesis of [ 936353-84-3 ]

* 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 [ 936353-84-3 ]

[ 936353-84-3 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 936353-84-3 ]
  • [ 1380106-79-5 ]
  • C24H29ClN4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 86℃; for 5.0h; General procedure: A mixture of 3-(4-bromo-2-chloro-phenyl)-N-(tetrahydropyran-2-yloxy)-acrylamide (70 mg, 0.194 mmol), pyridine-3-boronic acid (35.8 mg, 0.291 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (14.2 mg, 0.019 mmol) and potassium carbonate (42.9 mg, 0.31 mmol) in 1,4-dioxane (1.5 mL) and water (0.5 mL) was heated at 86 C for 5 h. After cooling down the reaction mixture was partitioned between water and ethyl acetate, the organic layer was dried over sodium sulfate, filtered, concentrated and purified by thin layer chromatography (1 mm) eluting with 40% ethyl acetate/hexanes to give the product as a white solid. This intermediate was dissolved in dichloromethane (1 mL), 4 N hydrogen chloride in dioxane (1 mL) was added. The reaction mixture was stirred at room temperature for 4 h and the precipitates were filtered. The solid was dried under vacuum to give 39 mg (Yield 65%, HPLC purity 100%) product as a white solid.
  • 2
  • [ 936353-84-3 ]
  • [ 1380106-79-5 ]
  • 3-{2-chloro-4-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-phenyl}-N-hydroxy-acrylamide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 1.5h;Microwave irradiation; General procedure: To a solution of 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (239 mg, 1 mmol) in NMP (2 mL) was added pyrrolidin-3-ol (174 mg, 2 mmol) and DIPEA (500 uL, 3 mmol), then the mixture was sealed in a microwave tube and heated in microwave reactor at 180 C. for 1.5 hours. TLC and LC-Ms showed the reaction had completed and the desired compound was detected. The reaction mixture was poured into 30 mL of H2O, and extracted with n-BuOH, washed with water and brine, concentrated and purified on TLC(CH2Cl2:MeOH=10:1) to give a white solid. MS
  • 4
  • [ 1192885-47-4 ]
  • [ 936353-84-3 ]
  • 2-(3-(3-methoxy-5-methylphenyl)-4-(2-(6-(4-methylpiprazine-1-yl)pyridin-3-yl)pyridin-4-yl)-1H-pyrazole-1-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; at 70℃; for 12.0h;Inert atmosphere; General procedure: A mixture of compound 4 (100 mg, 0.29 mmol), aryl boronic acid (0.35 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 0.013 mmol) and K2CO3 (71 mg, 0.52 mmol) was placed in a mixed solvent of THF and water (4:1, v/v, 10 mL). N2 gas was bubbled into this mixture for 10 min, and then the mixture was heated at 70 C while stirring under N2 for 12 h. The reaction mixture was left to cool at room temperature, and extracted with ethyl acetate (100 mL × 3). The combined organic extracts were dried over anhydrous MgSO4 and evaporated under vacuum. The target compounds 5a-j were separated in pure form by column chromatography (silica gel) using the proper ratio of ethyl acetate and n-hexane.
  • 5
  • [ 936353-84-3 ]
  • C11H8BrN5 [ No CAS ]
  • C21H22N8 [ No CAS ]
  • 6
  • [ 936353-84-3 ]
  • [ 1354745-85-9 ]
  • 6-chloro-7-methoxy-2-methyl-3-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)quinolin-4(1H)-one [ No CAS ]
  • 7
  • [ 936353-84-3 ]
  • 4-bromo-1-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indole-6-carboxamide [ No CAS ]
  • 1-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl) methyl)-4-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80 - 85℃; for 16.5h;Inert atmosphere; To a solution of 4-bromo-l-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-l,2-dihydro pyridin-3-yl)methyl)-lH-indole-6-carboxamide (Example 30, 300 mg, 0.654 mmol) and (lH-indazol-4-yl) boronic acid(6-(4-methylpiperazin-l-yl)pyridin-3-yl)boronic acid (202 mg, 0.916 mmol) in 1,4-dioxane (5 mL) was added water (2.500 mL) and bubbled argon gas for 30 minutes. PdCl2(dppf)-CH2Cl2 adduct (53.4 mg, 0.065 mmol) was added and the reaction mass was stirred at 80-85 C for 16 h. After completion of reaction, the reaction mixture was cooled to RT, filtered through celite, added water, extracted with ethyl acetate, concentrated and purified by column chromatography (silica gel, 5 % MeOH in chloroform) to obtain the title compound. Yield: 444 mg (80 ); JH NMR (CDCI3, 300 MHz): delta 11.48 (s, 1H), 8.33 (s, 1H), 8.02 (s, 1H), 7.77 (s, 1H), 7.61 (s, 1H), 6.95 (s, 1H), 6.88 (s, 1H), 6.52 (s, 1H), 5.89 (s, 1H), 5.23 (m, 1H), 4.32 (s, 2H), 3.53 (s, 4H), 2.66 (s, 3H), 2.42 (s, 4H), 2.23 (s, 3H), 2.12 (s, 3H), 2.09 (m, 2H), 1.56 (m, 2H), 1.47 (d, 6H, J=3.6Hz), 0.95 (m, 3H); MS (ESI+): m/z 555 (M+l)+; HPLC purity: 98.81 %.
  • 8
  • [ 936353-84-3 ]
  • 5-bromo-3-(ethyl (tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-yl)methyl)benzamide [ No CAS ]
  • 3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-yl)methyl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)benzamide [ No CAS ]
  • 9
  • [ 936353-84-3 ]
  • 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yltrifluoromethane sulfonate [ No CAS ]
  • 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; Sealed tube; In a pressure tube, a solution of 3-chloro-6-(i-methyl-1H-pyrazol-4-yl)pyrazolo[i,5- a]pyridin-4-yl trifluoromethanesulfonate (Intermediate P8; 15 mg, 0.039 mmol) in dioxane (0.5 mL) was treated with (6-(4-methylpiperazin-i-yl)pyridin-3-yl)boronic acid (13 mg, 0.059 mmol), 2 M Na2CO3(aq) (98 tL, 0.20 mmol) and Pd(PPh3)4 (2.3 mg, 0.0020 mmol). The reaction mixture was purged with nitrogen, sealed and then heated at 90 C overnight. After cooling to ambient temperature, the reaction mixture was diluted with water (25 mL) and extracted with DCM (25 mL) and then with a 5:95 solution of MeOHIDCM (2 x 25 mL). The combined organic extracts were dried over anhydrous MgSO4, vacuum filtered, and concentrated in vacuo. The crude residue was purified directly by reverse phase chromatography (5-60% ACN/water) to afford the title compound as a solid contaminated with triphenylphosphine oxide (9.0 mg). That material was purified by preparative thin layer silica chromatography (10:90 0.2 M NH3 in MeOH:DCM). The lower band was isolated, suspended in 10:90 MeOHIDCM with NH4OH, and then filtered. The filtrate was concentrated in vacuo to cleanly provide the title compound (7.1 mg, 44% yield). MS (apci) m/z = 408.1 (M+H).
  • 10
  • [ 936353-84-3 ]
  • 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yltrifluoromethane sulfonate [ No CAS ]
  • 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In a pressure tube a solution of 3-chloro-6-(i-methyl-1H-pyrazol-4-yl)pyrazolo[i,5- a]pyridin-4-yl trifluoromethanesulfonate (Intermediate P8; 95 mg, 0.25 0 mmol) in dioxane (3 mL) was treated with (6-(4-methylpiperazin-i-yl)pyridin-3-yl)boronic acid (82.7 mg, 0.374 mmol), 2 MNa2CO3(aq) (624 tL, 1.25 mmol) and Pd(PPh3)4 (14.4 mg, 0.0125 mmol). The reaction mixture was purged with nitrogen, sealed and then heated at 90 C overnight. After cooling to ambient temperature, the reaction mixture was diluted with water (25 mL) and extracted with a 10:90 solution of MeOHIDCM (3 x 25 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phase chromatography (5-60% ACN/water with 0.1 N HC1). The product was triturated in Et20 (5 mL) and then filtered. The isolated solids were rinsed with Et20 (3 mL) and dried in vacuo to afford the title compound (69.3 mg, 58% yield). MS (apci) m/z = 408.0 (M+H).
  • 11
  • [ 936353-84-3 ]
  • (S)-(-)-8-bromo-1-(1-(4-fluorophenyl)ethyl)-1H-[1,2,3]-triazolo[4,5-c]quinoline [ No CAS ]
  • (S)-1-(1-(4-fluorophenyl)ethyl)-8-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]quinoline [ No CAS ]
  • 12
  • [ 936353-84-3 ]
  • 3-bromo-5-(methylsulfonyl)-4H-1,2,4-triazole [ No CAS ]
  • C13H18N6O2S [ No CAS ]
  • 13
  • 9-bromo-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one [ No CAS ]
  • [ 936353-84-3 ]
  • 9-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.1% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 80℃; for 4.0h; General procedure: To a solution of compound 3(4.18 g, 10 mmol) in 1,4-dioxane at room temperature, we subsequentlyadded Pd(PPh3)4 (1.16 g, 1 mmol), K2CO3 (2.76 g, 20 mmol),and (2-oxoindolin-5 -yl)boronic acid (2.12 g, 12 mmol). Afterdegassing, the resulting mixture was heated to 80 C for 4 h beforecooling to room temperature. The solution was extracted withEtOAc. The organic layer was washed with water and brine, dried(MgSO4), filtered, and evaporated to dryness as a yellow solid. (3.89 g, 82.6% yield)
  • 14
  • [ 936353-84-3 ]
  • N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-bromobenzimidazole-4-carboxamide [ No CAS ]
  • N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-benzimidazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 140℃; for 0.166667h;Inert atmosphere; Sealed tube; Microwave irradiation; N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-bromobenzimidazole-4-carboxamide (187.5mg, 0.5mmol), <strong>[936353-84-3]6-(4-methylpiperazin-1-yl)pyridine-3-boronic acid</strong> (132.6 mg, 0.6 mmol), Na2CO3 (318 mg, 1.5 mmol) was dissolved in a mixture of ethylene glycol dimethyl ether and water (4 mL: 1 mL), and argon gas was bubbled in for 10 min. Pd(dppf)Cl2 (55.03 mg, 0.075 mmol) was added, and the reaction tube was sealed. The reaction was carried out at 140 C for 10 min under microwave irradiation. The reaction solution was spun and the residue was dissolved in methanol. Filter through diatomaceous earth, collect the filtrate, spin dry, Silica gel column chromatography gave a solid.
  • 15
  • [ 936353-84-3 ]
  • 8-(N-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methylamino)formyl-6-bromo-4-cyclohexyl-3,4-dihydro-2H-benzo[1,4]oxazine [ No CAS ]
  • 4-cyclohexyl-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)amide [ No CAS ]
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