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[ CAS No. 850567-56-5 ] {[proInfo.proName]}

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Chemical Structure| 850567-56-5
Chemical Structure| 850567-56-5
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Product Details of [ 850567-56-5 ]

CAS No. :850567-56-5 MDL No. :MFCD06659926
Formula : C12H17BClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KHGJUVPQSMKNFA-UHFFFAOYSA-N
M.W : 253.53 Pubchem ID :44118755
Synonyms :

Calculated chemistry of [ 850567-56-5 ]      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 : 2.81

Safety of [ 850567-56-5 ]

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

Application In Synthesis of [ 850567-56-5 ]

* 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 [ 850567-56-5 ]

[ 850567-56-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 15803-02-8 ]
  • [ 850567-56-5 ]
  • [ 1341981-04-1 ]
YieldReaction ConditionsOperation in experiment
44% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 130 - 150℃; for 0.5h;Microwave irradiation; Preparation 132: 2-Chloro-5-(1 -methyl-1 H-pyrazol-4-yl)aniline; [00302] To a mixture of <strong>[850567-56-5]3-amino-4-chlorophenylboronic acid pinacol ester</strong> (0.1 10g, 0.434 mmol), 4-bromo-1 -methylpyrazole (0.087 g, 0.54 mmol), 1 ,1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (2.5 mL) followed by 1 M aqueous sodium carbonate (0.99 mL, 0.99 mmol). The microwave vial was heated at 150C for 20 minutes under microwave irradiation. Further catalyst (0.005 g) was added and the vial was heated at 130C for 10 minutes under microwave irradiation. The reaction mixture was partitioned between ethyl acetate (55 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (2 x 13 mL), dried (Na2S04) and concentrated in vacuo. This residue was purified using preparative TLC eluting with 30% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :3) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :3) (2 x 5 mL) and acetone (3 x 4 mL) to give the title compound as an off- white solid (0.040 g, 44%). 1 H-NMR (500 MHz, DMSO-d6) 3.84 (s, 3H), 5.29 (s, 2H), 6.72 (dd, J = 2.1 , 8.2 Hz, 1 H), 6.94 (d, J = 2.1 Hz, 1 H), 7.14 (d, J = 8.2 Hz, 1 H), 7.68 (d, J = 0.7 Hz, 1 H), 7.98 (s, 1 H).
44% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; at 130 - 150℃; for 0.5h;Microwave irradiation; Preparation 132 2-Chloro-5-(1-methyl-1H-pyrazol-4-yl)aniline To a mixture of <strong>[850567-56-5]3-amino-4-chlorophenylboronic acid pinacol ester</strong> (0.110 g, 0.434 mmol), 4-bromo-1-methylpyrazole (0.087 g, 0.54 mmol), 1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (2.5 mL) followed by 1M aqueous sodium carbonate (0.99 mL, 0.99 mmol). The microwave vial was heated at 150 C. for 20 minutes under microwave irradiation. Further catalyst (0.005 g) was added and the vial was heated at 130 C. for 10 minutes under microwave irradiation. The reaction mixture was partitioned between ethyl acetate (55 mL) and a saturated aqueous NaHCO3 solution (15 mL). The organic layer was washed with a saturated aqueous NaHCO3 solution (2*13 mL), dried (Na2SO4) and concentrated in vacuo. This residue was purified using preparative TLC eluting with 30% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 2% MeOH in ethyl acetate/CH2Cl2 (v/v; 1:3) (20 mL). The silica was removed by filtration, washed with ethyl acetate/CH2Cl2 (v/v; 1:3) (2*5 mL) and acetone (3*4 mL) to give the title compound as an off-white solid (0.040 g, 44%). 1H-NMR (500 MHz, DMSO-d6) 3.84 (s, 3H), 5.29 (s, 2H), 6.72 (dd, J=2.1, 8.2 Hz, 1H), 6.94 (d, J=2.1 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 7.68 (d, J=0.7 Hz, 1H), 7.98 (s, 1H).
  • 2
  • [ 4595-59-9 ]
  • [ 850567-56-5 ]
  • [ 1400287-54-8 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Microwave irradiation; Preparation 134: 2-Chloro-4-(pyrimidin-5-yl)aniline; [00304] To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.1 10g, 0.434 mmol), 5-bromopyrimidine (0.090 g, 0.56 mmol), 1 ,1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (23 mg, 0.028 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1 .06 mmol). The microwave vial was heated at 150C for 15 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (15 mL), dried (Na2S04) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 20% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :5) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :1 ) (2 x 5 mL) and acetone (3 x 4 mL) to give the title compound as a white solid (0.075 g, 84%). 1 H-NMR (500 MHz, DMSO-d6) 5.72 (s, 2H), 6.91 (d, J = 8.4, 1 H), 7.51 (dd, J = 2.2, 8.3 Hz, 1 H), 7.72 (d, J = 2.2 Hz, 1 H), 9.04, 9.05 (2 x s, 3H).
  • 3
  • [ 56423-63-3 ]
  • [ 850567-56-5 ]
  • [ 1400287-53-7 ]
YieldReaction ConditionsOperation in experiment
44% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 75 - 90℃; for 1.75h;Microwave irradiation; Preparation 133: 2-Chloro-4-(pyrazin-2-yl)aniline; [00303] To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.1 10g, 0.434 mmol), 2-bromopyrazine (0.090 g, 0.56 mmol), 1 ,1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1 .06 mmol). The microwave vial was heated at 75C for 40 minutes under microwave irradiation. Further catalyst (0.012 g) was added and the vial was heated at 90C for 25 minutes under microwave irradiation. Further 2-bromopyrazine (0.060g), catalyst (12 mg) and 2M aqueous sodium carbonate (0.25 mL) were added and the reaction mixture was heated at 90C for an additional 30 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (2 x 15 mL), dried (Na2S04) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 7% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :10) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :5) (2x5 mL) and acetone (3 x 4 mL) to give the title compound as an off- white solid (0.039 g, 44%). 1 H-NMR (500 MHz, DMSO-d6) 5.86 (s, 2H), 6.89 (d, J = 8.5, 1 H), 7.85 (dd, J = 2.1 , 8.5 Hz, 1 H), 8.02 (d, J = 2.1 Hz, 1 H), 8.44 (d, J = 2.5 Hz, 1 H), 8.57 (dd, J = 1 .6, 2.5 Hz, 1 H), 9.12 (d, J = 1 .5 Hz, 1 H).
  • 4
  • [ 850567-56-5 ]
  • [ 73183-34-3 ]
  • [ 1417036-35-1 ]
  • 5
  • [ 850567-56-5 ]
  • [ 661-69-8 ]
  • [ 1565857-78-4 ]
  • 6
  • [ 73183-34-3 ]
  • [ 850567-56-5 ]
  • 7
  • [ 913836-26-7 ]
  • [ 850567-56-5 ]
YieldReaction ConditionsOperation in experiment
94% With iron; ammonium chloride; In ethanol; water; at 105℃; for 2.0h; Compound 1 (55.0 g, 190 mmol) was added to a three-neck flask.Ethanol (500 mL),Water (100 mL) andAmmonium chloride (20.4 g, 390 mmol);Iron powder (49 g, 880 mmol) was slowly added with stirring at room temperature.The reaction solution was heated to reflux at 105 C for 2 hours.After cooling to room temperature, Celite was filtered to remove excess iron; ethanol was distilled off under reduced pressure, and water (100 mL) and saturated aqueous sodium bicarbonate solution (150 mL) were added.Extraction with ethyl acetate (200 mL x 3); the organic phases were combined, washed with saturated aqueous sodium bicarbonate (150 mL) and saturated brine (150 mL), dried over sodium sulfate and filtered.The filtrate was spin-dried to give a yellow liquid, compound 2 (45.5 g, 179 mmol, 94%)
YieldReaction ConditionsOperation in experiment
75% General procedure: Step 3-Preparation of 3-aminophenylboronic acid pinacolate ester (2-(3-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane; Compound 6) from 3-aminophenylboronic acid hydrogen sulphate salt solution of Example 2. [0054] 1 V of Toluene was added to 300 g of 3-aminophenylboronic acid hydrogen sulphate salt solution (obtained at *point 1 of the previous example and containing about 202 mmoles of product) and, under stirring, the pH value of this mixture was corrected to a final pH value of 8,0 with NaOH 33%. 1 eq. Of Pinacol was added and the obtained reaction mixture maintained under stirring at room temperature until the conversion was complete. The organic phase was separated and evaporated under vacuum to residue. 1V of Heptane was added and the obtained slurry maintained under stirring at 20-25C for 1 hour to afford a precipitate that was recovered by filtration and dried under vacuum (200 mmHg) at 40C for 8 hours to give 36,5 g of compound 6 (169 mmoles; 84 % yields). [0055] Overall molar yields from Benzophenone (without isolation of intermediate compound 5): 61%
75% With sodium hydroxide; In water; at 20℃;pH 8.0; General procedure: Step 3Preparation of 3 -aminophenylboronic acid pinacolate ester (2- ( 3 -bromophenyl) -4 , 4 , 5 , 5- tetramethyl-1, 3 , 2 -Dioxaborolane ; Compound 6) from 3- aminophenylboronic acid hydrogen sulphate salt solution of Example 2IV of Toluene was added to 300 g of 3~ aminophenylboronic acid hydrogen sulphate salt solution (obtained at *point 1 of the previous example and containing about 202 mmoles of product) and, under stirring, the pH value of this mixture was corrected to a final pH value of 8,0 with NaOH 33%. 1 eq. Of Pinacol was added and the obtained reaction mixture maintained under stirring at room temperature until the conversion was complete. The organic phase was separated and evaporated under vacuum to residue. IV of Heptane was added and the obtained slurry maintained under stirring at 20-25C for 1 hour to afford a precipitate that was recovered by filtration and dried under vacuum (200 mmHg) at 40C for 8 hours to give 36,5 g of compound 6 {169 mmoles; 84 % yields) . Overall molar yields from Benzophenone (without isolation of intermediate compound 5) : 61%
  • 9
  • [ 195457-61-5 ]
  • [ 850567-56-5 ]
  • 6-(3-amino-4-chlorophenyl)-N-(3-chloro-4-fluorophenyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With potassium carbonate; In 1,4-dioxane; at 100℃; for 0.3h;Inert atmosphere; Sealed tube; Microwave irradiation; A mixture consisting of 6-bromo-N-(3-chlorophenyl)quinazolin-4-amine - HC1 (350 mg 0.90mmol), <strong>[850567-56-5]2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (251 mg, 0.99 mmol)and 1 .4M K2C03 (2.8 mL) in 10 mL of 1 ,4-dioxane was degassed (vacuum/nitrogen, 3 times).To the reaction mixture was added SiliCat DPP-Pd (150 mg, 0.26 mmol/g loading). The reactionmixture was sealed and heated at 100 C for 12 minutes in a Biotage Emrys Optimizer microwave. To the reaction mixture was added additional 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)aniline (40 mg, 0.16 mmol) and SiliCat DPP-Pd (30 mg). The reaction mixture was heated again at 100 C for 6 minutes and cooled. The aqueous phase was removedand the remaining organic phase was filtered through a glass frit. The solids were washed withmethanol. The filtrate was concentrated under reduced pressure. The residue was applied to a120 g silica column and eluted with a gradient of 35:65 to 75:25 ethyl acetate-heptane to give126 mg (35%) of the title compound as a colorless solid; MS (ES-API+) m/z 399.0 (M+1), 401.0 (Cl isotope), (ES-API-) m/z 397.0 (M-1), 399.0 (Cl isotope); ?H NMR (400 MHz, DMSO-d6) oe10.04 (s, 1H), 8.73 (d, J=1.74 Hz, 1H), 8.64 (s, 1H), 8.20 (dd, J=2.65, 6.86 Hz, 1H), 8.06 (dd,J=1.83, 8.69 Hz, 1H), 7.83-7.90 (m, 2H), 7.47 (t, J=9.10 Hz, 1H), 7.37 (d, J=8.23 Hz, 1H), 7.23(d, J2.20 Hz, 1H), 7.03 (dd, J2.20, 8.23 Hz, 1H), 5.51 (s, 2H).
  • 10
  • [ 850567-56-5 ]
  • trifluoromethanesulfonic acid 1-benzyl-5-methyl-1,4,5,6-tetrahydropyridin-3-yl ester [ No CAS ]
  • 5-(1-benzyl-5-methyl-1,4,5,6-tetrahydropyridin-3-yl)-2-chlorophenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.5% With bis(tri-t-butylphosphine)palladium(0); sodium carbonate; In 1,4-dioxane; water; at 45℃;Inert atmosphere; A mixture of trifluoro-methanesulfonic acid 1 -benzyl-5-methyl- 1,4,5 ,6-tetrahydro-pyridin-3 -yl ester (6097mg; 18.18 mmol), 2-Chloro-5-(4,4,5,5-tetramethyl- [1,3 ,2jdioxaborolan-2-yl)- phenylamine (4.61 g; 18.18 mmol), sodium carbonate (3.85 g; 36.36 mmol) in dioxane (150 ml)and water (15 ml) was degassed, added bis(tri-tert-butylphosphine) palladium (0) (464 mg; 0.91mmol). The mixture was stirred at 45C overnight. The reaction mixture was filtered and thefiltrate was concentrated. The crude was purified by Biotage silica gel column (340g, elutingwith hex/EA 0-35) to yield the title compound (2700 mg, yield 47.5%) LC-MS (M+1) =3 13/3 15.
  • 11
  • [ 850567-56-5 ]
  • (R)-3-methyl-5-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • (R)-5-(3-amino-4-chlorophenyl)-3-methyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With bis(tri-t-butylphosphine)palladium(0); sodium carbonate; In 1,4-dioxane; water; at 45℃;Inert atmosphere; A mixture of 3-Methyl-5-trifluoromethanesulfonyloxy-3,4- dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3237 mg; 9.37 mmol), 2-Chloro-5- (4,4,5 ,5-tetramethyl- [1,3 ,2j dioxaborolan-2-yl)-phenylamine (1.90 g; 7.50 mmol) and sodium carbonate (1.99 g; 18.75 mmol) in dioxane (150 ml) and water (15 ml) was degassed, and then added bis(tri-tert-butylphosphine)palladium(0) (239.52 mg; 0.47 mmol). The mixture was stirred at 45C overnight. The reaction mixture was filtered. The filtrate was concentrated. The curde was purified by Biotage silica gel column (150 g, eluted with hex/EA 0-35%) to yield (R)-5-(3- Amino-4-chloro-phenyl)-3 -methyl-3 ,6-dihydro-2H-pyridine- 1 -carboxylic acid tert-butyl ester as the major product (526mg, 18%). LC-MS (M+1) =323. 1HNMR (400 MHz, Chloroform-d) 7.41 (ddt, I = 8.9, 6.7, 1.8 Hz, 1H), 7.37 - 7.30 (m, 1H), 7.22 - 7.12 (m, 1H), 6.87 - 6.68 (m, 2H),4.11 - 3.74 (m, 3H), 2.51 - 2.40 (m, 1H), 2.10 - 1.94 (m, 2H), 1.55 (s, 9H), 1.10 (d, I = 6.1 Hz, 3H) and (R)-5-(3 -Amino-4-chloro-phenyl)-3 -methyl-3 ,4-dihydro-2H-pyridine- 1 -carboxylic acid tert-butyl ester (300mg, 10%). LC-MS (M+1) =323. 1HNMR (400 MHz, Chlorofonn-d) 7.21 (d, I = 8.3 Hz, 1H), 6.76 (dd, I = 22.4, 5.2 Hz, 2H), 6.01 (dt, I = 3.6, 1.9 Hz, 1H), 4.32 (d, I = 17.5 Hz, 1H), 4.09 (d, I = 23.5 Hz, 2H), 2.93 (d, I = 51.9 Hz, 1H), 2.50 (s, 1H), 1.52 (s, 9H),1.33 - 1.24 (m, 3H), 1.08 (d, I = 7.1 Hz, 3H).
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; ;