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[ CAS No. 915201-07-9 ] {[proInfo.proName]}

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Chemical Structure| 915201-07-9
Chemical Structure| 915201-07-9
Structure of 915201-07-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 915201-07-9 ]

CAS No. :915201-07-9 MDL No. :MFCD03095046
Formula : C7H8BClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WAVZSRUGKKOQRB-UHFFFAOYSA-N
M.W : 186.40 Pubchem ID :17750234
Synonyms :

Calculated chemistry of [ 915201-07-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.77
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 0.03
Log Po/w (MLOGP) : 0.6
Log Po/w (SILICOS-IT) : -0.1
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.37 mg/ml ; 0.00734 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.56 mg/ml ; 0.00834 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.03
Solubility : 1.73 mg/ml ; 0.00927 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 915201-07-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338 UN#:1759
Hazard Statements:H302-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 915201-07-9 ]

* 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 [ 915201-07-9 ]

[ 915201-07-9 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 915201-07-9 ]
  • [ 216485-72-2 ]
  • (5'-chloro-6-methanesulfonyl-3'-methoxy-2-methyl-biphenyl-3-yl)-(1-ethyl-5-hydroxy-1<i>H</i>-pyrazol-4-yl)-methanone [ No CAS ]
  • 3
  • [ 108-69-0 ]
  • [ 915201-07-9 ]
  • N-(3,5-dimethylphenyl)-3-chloro-5-methoxyphenylamine [ No CAS ]
  • 4
  • [ 929626-16-4 ]
  • [ 915201-07-9 ]
  • 6
  • [ 151266-23-8 ]
  • [ 915201-07-9 ]
  • 3-(3-chloro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 80℃; for 12.5h;Inert atmosphere; Intermediate 82 3-(3-chloro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.700 g, 2.68 mmoles) in DMF (10 ml), ethanol (6 ml) and water (6 ml), 3-chloro-5-methoxyphenyl boroinc acid (0.600 g, 3.21 mmoles) and sodium carbonate (1.40, 13.40 mmoles) were added and the system is degassed for 30 min. Tetrakis triphenylphosphine Palladium (0.610 g, 0.528 mmoles) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as yellow solid (0.198 g, 27% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 13.66 (s, 1H), 8.21 (s, 1H), 7.24 (t, J=1.6 Hz, 1H), 7.13 (d, J=1.2 Hz, 1H), 7.11 (t, J=2.1 Hz, 1H), 3.83 (s, 3H).
  • 7
  • [ 915201-07-9 ]
  • [ 1300584-66-0 ]
  • 8
  • [ 915201-07-9 ]
  • [ 1300584-68-2 ]
  • 9
  • [ 870823-05-5 ]
  • [ 915201-07-9 ]
  • C37H38ClN3O5 [ No CAS ]
  • 10
  • [ 1422978-17-3 ]
  • [ 915201-07-9 ]
  • [ 1621256-03-8 ]
YieldReaction ConditionsOperation in experiment
58.3% With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave irradiation; Intermediate compound62b:(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((2-(3-chloro-5-methoxyphenyl)-5,5-dimethylcyclohex-1-enyl)methyl)-4-methoxyoxazolidin-2-one[1128]Starting material16(0.500 g, 2.682 mmol), <strong>[915201-07-9]3-chloro-5-methoxyphenyl boronic acid</strong> (1.380 g, 2.682 mmol), Pd(di-t-Bupf)Cl2(0.087 g, 0.134 mmol) and sodium carbonate (0.569 g, 5.365 mmol) were added to dimethoxyethane (6 mL)/water (2 mL) and heated by microwave irradiation at 120 for 15 minutes. Then, the reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried with anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified and concentrated by MPLC (SiO2, EtOAc/hexane = 0% ~ 15%) to obtain desired compound62b(0.900 g, 58.3 %) as a brown foam solid.
  • 11
  • 2-((5-(3-bromophenyl)-1H-1,2,4-triazol-3-yl)thio)acetic acid [ No CAS ]
  • [ 915201-07-9 ]
  • 2-((5-(3’-chloro-5’-methoxy-[1,1’-biphenyl]-3-yl)-1H-1,2,4-triazol-3-yl)thio)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In acetonitrile; at 150℃; for 0.166667h;Sealed tube; Microwave irradiation; Example 6 Preparation of 2-((5-(3'-chloro-5'-methoxy-[1,1'-biphenyl]-3-yl)-1H-1,2,4-triazol-3-yl)thio)acetic acid General Synthetic Scheme for Arylation: 2-((5-(3-bromophenyl)-1H-1,2,4-triazol-3-yl)thio)acetic acid (20 mg, 0.063 mmol) was dissolve in anhydrous acetonitrile (1 ml) in a vial and <strong>[915201-07-9](3-chloro-5-methoxyphenyl)boronic acid</strong> (28 mg), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II)), (5 mg) and K2PO3 solution (2M, 500 mul) were added. The vial was sealed and heated for 10 m in a microwave reactor at 150 C. The pure product was isolated by automated LC/MS purification upon evaporation to dryness.
  • 12
  • [ 4408-64-4 ]
  • [ 915201-07-9 ]
  • C12H13BClNO5 [ No CAS ]
  • 13
  • (P)-1-(4-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide [ No CAS ]
  • [ 915201-07-9 ]
  • (P)-1-(3'-chloro-3,5'-dimethoxy-4-biphenylyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.4% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 50℃; for 4h; A vial charged with Pd(PPh3)4 (74.5 mg, 0.064 mmol), <strong>[915201-07-9](3-chloro-5-methoxyphenyl)boronic acid</strong> (235 mg, 1.26 mmol), (P)-1-(4-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (307 mg, 0.645 mmol), potassium carbonate (356 mg, 2.58 mmol) and 3 mL dioxane and 1 mL water was heated to 50 C. for 4 hours. The reaction mixture was allowed to cool to room temperature and HCl 4N in dioxane (1611 mul, 1.11, 6.45 mmol) was added. The reaction mixture was then concentrated. Purification of the crude residue by reverse phase column chromatography [puriflash C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave (P)-1-(3'-chloro-3,5'-dimethoxy-4-biphenylyl)-n-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide (0.092 g, 0.17 mmol, 54.4%). 1H NMR (ACETONITRILE-d3) ?: 8.35 (d, J=1.8 Hz, 1H), 8.25 (d, J=2.2 Hz, 1H), 7.98 (d, J=9.5 Hz, 1H), 7.80 (dd, J=9.0, 2.2 Hz, 1H), 7.36-7.47 (m, 3H), 7.30 (d, J=8.1 Hz, 1H), 7.23 (dd, J=2.4, 1.6 Hz, 1H), 7.01-7.07 (m, 1H), 6.73-6.81 (m, 2H), 6.42-6.46 (m, 1H), 3.88 (s, 3H), 3.77 (s, 3H). m/z (ESI) 538.2 (M+H)+.
  • 14
  • (P)-perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate [ No CAS ]
  • [ 915201-07-9 ]
  • (P)-perfluorophenyl 1-(3'-chloro-3,5'-dimethoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.0% A RBF was charged with (P)-perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (1.475, 2.56 mmol), 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (181 mg, 0.256 mmol), and cesium carbonate (3336 mg, 10.24 mmol). The flask was flushed with Ar (g), then DMF (12.4 mL) was added. The flask was lowered into a 50 C. heating bath. After 3 min, a solid mixture of <strong>[915201-07-9](3-chloro-5-methoxyphenyl)boronic acid</strong> (1431 mg, 7.68 mmol) and copper(I) chloride (760 mg, 7.68 mmol) was added directly. After 50 min, the mixture was cooled, diluted with EtOAc, and filtered through celite. The filtrate was concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel column, 0-40% EtOAc/Heptane). Fractions containing pure product were combined and concentrated to give (P)-perfluorophenyl 1-(3'-chloro-3,5'-dimethoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (980 mg, 1.536 mmol, 60.0% yield) as a pink foam. m/z (ESI) 638.0 (M+H)+.
  • 15
  • methyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate [ No CAS ]
  • [ 915201-07-9 ]
  • 4-(3-chloro-5-methoxyphenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid [ No CAS ]
  • 16
  • 6-(tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine [ No CAS ]
  • [ 915201-07-9 ]
  • 6-(tert-butylsulfonyl)-3-(3-chloro-5-methoxyphenyl)-7-methoxyimidazo[1,2-a]pyridine [ No CAS ]
  • 17
  • 6-(1-(5-bromo-2-methoxyphenyl)-3-methylureido)-N-(isoxazol-3-yl)pyridine-3-sulfonamide [ No CAS ]
  • [ 915201-07-9 ]
  • 6-((3‘-chloro-4,5‘-dimethoxy-3-biphenylyl)(methylcarbamoyl)amino)-N-3-isoxazolyl-3-pyridinesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.2% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; under 760.051 Torr; for 1.5h;Inert atmosphere; To a vial containing 6-(1-(5-bromo-2-methoxyphenyl)-3-methylureido)- N-(isoxazol-3-yl)pyridine-3 -sulfonamide (100 mg, 0.207 mmol), (3-chloro-5- methoxyphenyl)boronic acid (58 mg, 0.311 mmol), potassium carbonate (86 mg, 0.622 mmol), and tetrakis(triphenylphosphine) palladium (24 mg, 0.021 mmol) were added 1,4- dioxane (0.78 mL) and water (0.26 mL). The reaction mixture was purged under nitrogen and was then heated to 80C for 90 mins, until reaction complete as shown by LCMS. The reaction was cooled to RT and partitioned between saturated aqueous NH4C1 and DCM. The organic phase was separated and the aqueous phase was further extracted with DCM (2x). The combined organic layers were then dried with Mg504, filtered and concentrated in vacuo. The resulting crude material was absorbed onto a plug of silica gel and purified by chromatography through a RediSep Rf Gold pre-packed silica gel column (12 g), eluting with a gradient of 50% to 90% ethyl acetate in heptane, to provide 6-(1 -(3 ?-chloro-4,5 ?-dimethoxy- [1,1? -biphenylj -3 -yl)-3 -methylureido)-N-(isoxazol-3- yl)pyridine-3-sulfonamide (63.4 mg, 0.117 mmol, 56.2% yield) as white solid, (see Table 7 for analytical data).
  • 18
  • C21H24N4O4S [ No CAS ]
  • [ 915201-07-9 ]
  • (S)-1-(3-chloro-5-methoxyphenyl)-5-(5-(3,5-dimethylisoxazol-4-yl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-benzo[d]imidazol-2-yl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 40℃; for 18h; A solution of DBU (22 mu,, 0.146 mmol) and Intermediate E3 (60 mg, 0.139 mmol) in acetonitrile (4 mL) was added to a vial charged with CuTMEDA (10 mg, 0.022 mmol) and <strong>[915201-07-9](3-chloro-5-methoxyphenyl)boronic acid</strong> (28 mg, 0.150 mmol) before stirring for 18 h at 40C. The mixture was concentrated under reduced pressure then purified by chromatography on the Companion (4 g column, 0-50% MeAc/DCM) to afford a colourless gum. The gum was dissolved in methyl ethyl ketone (0.5 mL) then diluted with diethyl ether. The supernatant was removed then the solid was dried overnight in a desiccator at 50C to yield (,S)-l-(3-chloro-5-methoxyphenyl)-5-(5-(3,5- dimethylisoxazol-4-yl)- 1 -( 1 , 1 -dioxidotetrahydro-2H-thiopyran-4-yl)- 1H- benzo[<i]imidazol-2-yl)pyrrolidin-2-one (47 mg, 57%) as a white solid; Rt 1.94 min (method 1), m/z 569 (M+H)+ (ES+); 1H MR (d6-DMSO) delta: 7.66 (d, J = 1.6 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.33 (t, J = 1.9 Hz, 1H), 7.30 (dd, J = 8.5, 1.7 Hz, 1H), 7.06 (t, J = 2.1 Hz, 1H), 6.79 (t, J = 2.0 Hz, 1H), 6.05 (d, J = 7.5 Hz, 1H), 5.16 - 4.99 (m, 1H), 3.69 (s, 3H), 3.64 - 3.51 (m, 2H), 3.33 - 3.26 (m, 2H), 3.02 - 2.83 (m, 2H), 2.83 - 2.52 (m, 3H), 2.38 (s, 3H), 2.35 - 2.23 (m, 1H), 2.21 (s, 3H), 2.19 - 2.08 (m, 2H; Chiral HPLC (Diacel Chiralpak IA, 5 mupiiota, 4.6x250 mm, 30 min method, 1.0 mL/min, isocratic 30% EtOH in isohexane (0.2% TFA): 148485, RT = 10.72 min, >99%, >98% de 254 nm.
  • 19
  • (S)-5-(5-(3,5-dimethylisoxazol-4-yl)-1-((R)-1-(methylsulfonyl)pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-yl)pyrrolidin-2-one [ No CAS ]
  • [ 915201-07-9 ]
  • (S)-1-(3-chloro-5-methoxyphenyl)-5-(5-(3,5-dimethylisoxazol-4-yl)-1-((R)-1-(methylsulfonyl)pyrrolidin-3-yl)1H-benzo[d]imidazol-2-yl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 40℃; for 2h; DBU (25 mu, 0.166 mmol) was added to a solution of Intermediate El (70 mg, 0.156 mmol) in acetonitrile (5 mL) then stirred for 5 minutes. CuTMEDA (10 mg, 0.022 mmol) was added and the suspension was stirred for a further 2 minutes before adding <strong>[915201-07-9](3-chloro-5-methoxyphenyl)boronic acid</strong> (33 mg, 0.177 mmol) and stirring for 2 h at 40C. The mixture was concentrated under reduced pressure then purified by chromatography on the Companion (4 g column, 0-50% MeAc/DCM) to afford (-S)-l- (3-chloro-5-methoxyphenyl)-5-(5-(3,5-dimethylisoxazol-4-yl)-l-((R)-l- (methylsulfonyl)pyrrolidin-3-yl)-lH-benzo[
  • 20
  • [ 1899-24-7 ]
  • [ 915201-07-9 ]
  • 5-(3-chloro-5-methoxyphenyl)furan-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 70℃;Inert atmosphere; Sealed tube; General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9).
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