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[ CAS No. 721960-43-6 ] {[proInfo.proName]}

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Chemical Structure| 721960-43-6
Chemical Structure| 721960-43-6
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Product Details of [ 721960-43-6 ]

CAS No. :721960-43-6 MDL No. :MFCD09998359
Formula : C12H17BClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BEXOYZKPTUJSCZ-UHFFFAOYSA-N
M.W : 253.53 Pubchem ID :44118796
Synonyms :

Calculated chemistry of [ 721960-43-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.33
TPSA : 44.48 ?2

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 : Yes
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.0989 mg/ml ; 0.00039 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0893 mg/ml ; 0.000352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.26
Solubility : 0.014 mg/ml ; 0.0000552 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.76

Safety of [ 721960-43-6 ]

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 [ 721960-43-6 ]

* 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 [ 721960-43-6 ]

[ 721960-43-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 38762-41-3 ]
  • [ 25015-63-8 ]
  • [ 721960-43-6 ]
YieldReaction ConditionsOperation in experiment
50% A. To a solution of 4-bromo-2-chloro-phenylamine (4.2 g, 20 MMOL), in dioxane (80 mL) was added triethylamine (10 mL, 72 MMOL). The pale yellow solution was sparged with nitrogen. During the nitrogen sparge, 4,4, 5, 5-tetramethyl- [1,3, 2] DIOXABOROLANE (8.5 mL, 59 MMOL) was added dropwise over 10 minutes. After 20 minutes the nitrogen sparge was discontinued and dichloro [1,1'- bis (diphenylphosphino) ferrocene) PALLADIUM (II) DICHLOROMETHANE adduct (603 mg, 0.74 MMOL) was added. The reaction was then heated to 100C in a temperature controlled heating mantle. After stirring for 20 hours at 100C, HPLC analysis of the reaction showed clean conversion to a product. The reaction was allowed to cool to ambient temperature and diluted with ET20 (250 mL) and H20 (100 ML). The resulting brown biphasic suspension was filtered to remove some solids that had formed. The layers were separated, and the aqueous layer was extracted with ET20 (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over NA2SO4, then filtered and concentrated under reduced pressure to afford a brown oil, which partially solidified after standing at ambient temperature. This crude product was purified by silica gel column chromatography eluting with a gradient from 0% to 20% ethyl acetate /hexane on silica. The product peak was collected to afford 2-CHLORO-4- (4, 4,5, 5- tetramethyl- [1, 3,2] DIOXABOROLAN-2-YL)-PHENYLAMINE (2.6 g, 50% yield) as an off-white SOLID. 1H-NMR (400 MHz, CDCI3) : 5 7.69 (1H, d, J = 1.3 Hz), 7.49 (1H, dd, J = 8.1, 1.3 Hz), 6.72 (1H, d, J = 8.1 Hz), 4.25 (2H, br s), 1.31 (12H, s).
  • 2
  • [ 721960-43-6 ]
  • [ 41841-16-1 ]
  • [ 871476-59-4 ]
YieldReaction ConditionsOperation in experiment
48% g) Compound 1.8; To a solution of methyl (4-bromophenyl) acetate (obtained from the corresponding acid (267.5 mg, 1.2 mmol) upon treatment with excess diazomethane) in 1,4-dioxane (5 mL) were added intermediate 1.7 (315 mg, 1.20 mmol) and K3P04 (792 mg, 3.73 mmol). After degassing the reaction mixture for 45 min, PdCl2 (dppf) mg, 0.19 mmol) and dppf (136 mg, 0.06 mmol) were added and the mixture was heated at 100C for 3 h. After cooling to room temperature the reaction mixture was diluted with EtOAc, washed successively with water and brine, dried (MgS04), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using hexane/EtOAc (80/20) to give compound 1.8 (164 mg, 48% yield)
  • 3
  • [ 38762-41-3 ]
  • [ 73183-34-3 ]
  • [ 721960-43-6 ]
YieldReaction ConditionsOperation in experiment
63% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 6h; Synthesis of 2-chloro-4-(4,4, 5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline (22):A mixture of 4-bromo-2-chloroaniline (5 g, 24.4 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?- bi(1,3,2-dioxaborolane) (6.8 g, 26.8 mmol), Pd(dppf)C12 (1.8 g, 2.4 mmol) and KOAc (4.8 g, 48.8 mmol) in dioxane (80 mL) was degassed and heated at 100C for 6 h. After cooling down to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography (0-25% EtOAc/petroleum ether) to give 4.7 g of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 22 as yellow solid (63% yield). LCMS: m/z 254.1 [M+H], , tR= 2.02 min
63% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 6h; A mixture of 4-bromo-2-chloroaniline (5 g, 24.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2-dioxaborolane) (6.8 g, 26.8 mmol), Pd(dppf)Cl2 (1.8 g, 2.4 mmol) and KOAc (4.8 g, 48.8 mmol) in dioxane (80 mL) was degassed and heated at 100 C for 6 h. After cooling to room temperature the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography (0-25% EtO Ac/petroleum ether) to give 4.7 g of 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (30) (63% yield). LCMS: m/z 254.1 [M+H]+tR= 2.02 min
60% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; water; at 80℃; Compound 12-2 (0403) A solution of 12-1 (12.3 g, 0.06 mmol), Bis(pinacolato)diboron (18.3 g, 0.072 mol), KOAc (11.75 g, 0.12 mmol) and Pd(dppf)2Cl2DCM (2.0 g, 2.45 mmol) in dioxane/H2O (v/v=9/1, 100 mL) was stirred at 80 C. overnight. TLC showed that the reaction was complete. The mixture was evaporated to afford a brown oil. Water (60 mL) was added and the mixture was extracted with ethyl acetate (60 mL×3). The combined organic layers were dried over MgSO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=10:1) to afford 12-2 as a yellow solid (9.1 g, 60%).
44% f) Compound 1.7; A solution of 4-bromo-2-chloroaniline (4.00 g, 19.37 mmol), bis(pinacolato)diboron (5.90 g, 23.2 mmol) and KOAc (12.3 g, 58.1 mmol) in DMSO (100 mL) was deoxygenated by bubbling nitrogen through it for 45 min. PdCl2 (dppf) g, 1.94 mmol) and dppf (1.07 g, 1.94 mmol) were then added and the mixture was heated at 100C for 4 h. After cooling to room temperature the reaction mixture was diluted with EtOAc, washed successively with water and brine, dried (MgS04), filtered and concentrated under reduced pressure. The crude product was purified twice by flash chromatography using CH2Cl2 to give intermediate 1.7 (2.15 g, 44% yield) as a white solid.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 18h;Reflux; Inert atmosphere; Step 7: Synthesis of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (28) A mixture of compound 4-bromo-2-chloroaniline 27 (28 g, 0.135 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (44.76 g, 0.176 mol), KOAc (16.66 g, 0.17 mol) and Pd(dppf)Cl2 (5.4 g) was refluxed in 300 mL of dry dioxane under N2 for 18 h. This mixture was filtered and the filtrate was diluted with water (500 mL) and extracted with EtOAc (3*200 mL). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated to afford 50 g of crude 28, which was used directly in the next step. LCMS m/z 254 (M+H)+

YieldReaction ConditionsOperation in experiment
3.14 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 85℃; for 4.5h;Inert atmosphere; General procedure: 2.1: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 5.0 g (21.1 mmol) of 2-fluoro-4-iodoaniline and 5.89 g (23.2 mmol) of bis(pinacolato)diborane are dissolved in 130 ml of DMSO. 6.21 g (63.3 mmol) of potassium actetate are added and argon is bubbled through for 10 min. 1.21 g (1.50 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complexed with dichloromethane (1:1), is added and the mixture is heated at 85 C. for 4.5 hours, under argon, and then cooled and diluted with 500 ml of water. The mixture is extracted with ethyl acetate (3*200 ml), the organic phases are washed with water, dried over Na2SO4 and then evaporated to dryness. The crude product is purified by chromatography on silica (eluent: cyclohexane/ethyl acetate 90/10). 3.73 g of product are obtained in the form of a white powder. Yield=75%. Melting point: 112 C. 1H NMR (400 MHz; CDCl3): delta (ppm): 1.2 (s; 12H); 3.8 (br s; 2H); 6.55 (t; 1H; 7 Hz); 7.25-7.35 (m; 2H).
  • 5
  • [ 721960-43-6 ]
  • [ 1276129-91-9 ]
  • 6
  • [ 721960-43-6 ]
  • [ 1276129-61-3 ]
  • 7
  • [ 721960-43-6 ]
  • [ 1276129-46-4 ]
  • [ 1276129-50-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃; To a slurry of 34 (500 mg, 0.85 mmol), <strong>[721960-43-6]4-amino-3-chlorophenylboronic acid pinacol ester</strong> (465 mg, 1.84 mmol) and Pd(PPh3)4 (250 mg) in DMF (5 mL) was added aq. sat'd. Na2CO3 (3.5 mL). The reaction mixture was stirred at 100 C. until the starting material was consumed. The reaction mixture was cooled to RT then quenched H2O. The resulting precipitate was filtered then sequentially washed with hexanes/EtOAc and hexanes/DCM to yield 417 mg of 6-(4-amino-3-chloro-phenyl)-1-(4-chloro-benzyl)-1H-thieno[3,2-d]pyrimidin-4-one (40): MS calcd for C19H13Cl2N3OS [M+H]+ 402. Found, 402.
  • 8
  • [ 721960-43-6 ]
  • [ 92525-10-5 ]
  • [ 1400287-22-0 ]
YieldReaction ConditionsOperation in experiment
73% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 135℃; for 1h;Microwave irradiation; Preparation 85: 2-Chloro-4-(1 -methyl-1 H-pyrazol-3-yl)anilineMethod C; [00255] Tetrakis(triphenylphosphine)palladium (0.046g, 0.039mmol) was added to a solution of 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.394mmol), 3-iodo-1 -methyl-1 H-pyrazole (0.123g, 0.592mmol) and sodium carbonate (0.125g, 1 .183mmol) in DME/H20 3/1 (2.00ml_). The reaction mixture was heated for 1 hour at 135C under microwave irradiation before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a yellow solid (60mg, 73%). 1 H NMR (500 MHz, CDCI3): delta 3.93 (s, 3H), 4.09 (br s, 2H), 6.42 (d, J = 2.3Hz, 1 H), 6.79 (d, J = 8.3Hz, 1 H), 7.34 (d, J = 2.3Hz, 1 H), 7.50 (dd, J = 8.3, 2.0Hz, 1 H), 7.71 (d, J = 2.0Hz, 1 H). LC (Method B)-MS (ESI, m/z) fR 2.35 min, 208 [(M+H+), 100%].
73% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 135℃; for 1h;Microwave irradiation; Method C Tetrakis(triphenylphosphine)palladium (0.046 g, 0.039 mmol) was added to a solution of <strong>[721960-43-6]2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (0.1 g, 0.394 mmol), 3-iodo-1-methyl-1H-pyrazole (0.123 g, 0.592 mmol) and sodium carbonate (0.125 g, 1.183 mmol) in DME/H2O 3/1 (2.00 mL). The reaction mixture was heated for 1 hour at 135 C. under microwave irradiation before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a yellow solid (60 mg, 73%). 1H NMR (500 MHz, CDCl3): delta 3.93 (s, 3H), 4.09 (br s, 2H), 6.42 (d, J=2.3 Hz, 1H), 6.79 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.3 Hz, 1H), 7.50 (dd, J=8.3, 2.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 2.35 min, 208 [(M+H+), 100%].
  • 9
  • [ 721960-43-6 ]
  • [ 1432909-93-7 ]
  • 10
  • [ 721960-43-6 ]
  • [ 1432909-94-8 ]
  • 11
  • [ 721960-43-6 ]
  • [ 1432909-95-9 ]
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; ;