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[ CAS No. 859855-53-1 ] {[proInfo.proName]}

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Chemical Structure| 859855-53-1
Chemical Structure| 859855-53-1
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Quality Control of [ 859855-53-1 ]

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Product Details of [ 859855-53-1 ]

CAS No. :859855-53-1 MDL No. :MFCD07787428
Formula : C7H5FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BHMZMZOMQYFFQL-UHFFFAOYSA-N
M.W : 136.13 Pubchem ID :15251694
Synonyms :

Calculated chemistry of [ 859855-53-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.52
TPSA : 49.81 ?2

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 : Yes
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 1.88 mg/ml ; 0.0138 mol/l
Class : Very soluble
Log S (Ali) : -1.8
Solubility : 2.15 mg/ml ; 0.0158 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.578 mg/ml ; 0.00425 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 859855-53-1 ]

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 [ 859855-53-1 ]

* 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 [ 859855-53-1 ]

[ 859855-53-1 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 1009-35-4 ]
  • [ 859855-53-1 ]
YieldReaction ConditionsOperation in experiment
97% With 5%-palladium/activated carbon; hydrogen; In ethanol; under 12001.2 Torr;Flow reactor; General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.
91% Step A 3-amino-4-fluorobenzonitrile Using 4-fluoro-3-nitrobenzonitrile (13.64 g, 82.11 mmol) and according to the method of Reference Example 68, step A, the title compound (10.16 g, yield 91%) was obtained as a pale-yellow solid. 1H-NMR (300 MHz, CDCl3); delta(ppm) 3.94 (brs, 2H), 7.00-7.09 (m, 3H).
87% With iron; ammonium chloride; In water; isopropyl alcohol; for 4h;Reflux; Intermediate 1: 3-Amino-4-fluoro benzonitrile; A solution of 4-fluoro-3-nitro benzonitrile (Combi-Blocks; 5.0 g; 30 mmol) and saturated solution of ammonium chloride (16 g; 0.3 mol in 20ml of water) in iPrOH (100 ml) was treated with iron powder (8.4 g; 0.15 mol) and refluxed for 4h. The mixture was cooled and diluted with ethyl acetate (200ml) and the organic phase was washed with water, brine and dried on MgSO^ The solvents were evaporated under reduced pressure and the residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the Title compound (3.5 g, 87%) as a solid.1H NMR (300MHz, DMSO-dg) delta [ppm] 7.21-7.17 (m, IH), 7.10-7.07 (m, IH), 6.98-6.94 (m, IH), 5.70 (bs, 2H). MS (ESI+): 136.9.
With hydrogen;5%-palladium/activated carbon; In methanol; under 1500.15 Torr; for 2h; 4-fluoro-3-nitrobenzonitrile (5 g, 30 mmol) is first of all subjected to catalytic hydrogenation with 5% palladium on activated charcoal (0.4 g) in 300 mL methanol (2 h at 2 bar hydrogen pressure), whereupon the 3-amino-4-fluorobenzonitrile formed is obtained as a solid after filtration and evaporation of the solvent. Yield: 4.1 g.
With iron; acetic acid; at 80℃; for 1h;Inert atmosphere; A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C. for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2CO3 and extracted with DCM (2×200 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to yield 3-amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1)+.; To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (3.0 g, 18.5 mmol) in anhydrous dichloromethane (50 mL) at 0 C. was added dropwise oxalyl chloride (4.84 mL, 55.5 mmol). Then, three drops of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 3-amino-4-fluorobenzonitrile (48) (2.5 g, 18.5 mmol) in anhydrous pyridine (50 mL) at room temperature. The reaction was stirred for 20 minutes and quenched with water (200 mL) with stirring for another 10 minutes. Then the precipitate was filtered and dried in air to yield N-(5-cyano-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (49). 1H NMR (400 MHz, d6-DMSO) delta 10.40 (s, 1H), 9.43 (td, J=1.2, 6.8 Hz, 1H), 8.63 (s, 1H), 8.21 (dd, J=2.0, 7.2 Hz, 1H), 7.78-7.84 (m, 2H), 7.54-7.63 (m, 2H), 7.22 (dt, J=1.2, 6.8, 1H). MS m/z 281.1 (M+1)+.; NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5-cyano-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70 C. for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N?-hydroxycarbamimidoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (50). 1H NMR (400 MHz, d6-DMSO) delta 10.21 (s, 1H), 9.70 (s, 1H), 9.45 (td, J=1.2, 7.2 Hz, 1H), 8.61 (s, 1H), 7.95 (dd, J=2.4, 7.6 Hz, 1H), 7.79 (td, J=1.2, 8.8 Hz, 1H), 7.51-7.60 (m, 2H), 7.31-7.37 (m, 1H), 7.19 (dt, J=1.2, 6.8, 1H), 5.88 (s, 2H). MS m/z 314.1 (M+1)+.
A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2C03 and extracted with DCM (2 x 200 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to yield 3- amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1 ) +.
A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C. for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2CO3 and extracted with DCM (2×200 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to yield 3-amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1)+.
With iron; acetic acid; at 80℃; for 1h;Inert atmosphere; A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2C03 and extracted with DCM (2 x 200 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to yield 3- amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1 ) +. To a stirring suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (3.0 g, 18.5 mmol) in anhydrous dichloromethane (50 mL) at 0 C was added dropwise oxalyl chloride (4.84 mL, 55.5 mmol). Then, three drops of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 3-amino-4- fluorobenzonitrile (48) (2.5 g, 18.5 mmol) in anhydrous pyridine (50 mL) at room temperature. The reaction was stirred for 20 minutes and quenched with water (200 mL) with stirring for another 10 minutes. Then the precipitate was filtered and dried in air to yield N-(5-cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49). 1 H NMR (400MHz, c/6-DMSO) delta 10.40 (s, 1 H), 9.43 (td, J = 1 .2, 6.8 Hz, 1 H), 8.63 (s, 1 H), 8.21(dd, J = 2.0, 7.2 Hz, 1 H), 7.78-7.84 (m , 2H), 7.54-7.63 (m , 2H), 7.22 (dt, J = 1 .2, 6.8, 1 H). MS m/z 281 .1 (M+1 ) +. NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70 C for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N'- hydroxycarbamimidoyl)phenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (50). 1 H NMR (400MHz, c/6-DMSO) delta 10.21 (s, 1 H), 9.70 (s, 1 H), 9.45 (td, J = 1 .2, 7.2 Hz, 1 H), 8.61 (s, 1 H), 7.95 (dd, J = 2.4, 7.6 Hz, 1 H), 7.79 (td, J = 1 .2, 8.8 Hz, 1 H), 7.51 -7.60 (m , 2H), 7.31 -7.37 (m, 1 H), 7.19 (dt, J = 1 .2, 6.8, 1 H), 5.88 (s, 2H). MS m/z 314.1 (M+1 ) +.
With sodium hydrogencarbonate; tin(ll) chloride; In ethyl acetate; 4-Fluoro-3-nitrobenzonitrile (1) (2 g, 0.012 mol) in ethyl acetate(50 mL) was supplemented with stannous chloride (11.4 g,0.06 mol). The reaction mixture was stirred for 30 min and then a saturated solution of sodium hydrogenocarbonate (100 mL) was added. This mixture was treated with ethyl acetate (300 mL) andthe aqueous layer was separated. The ethyl acetate layer was evaporated under reduced pressure. The crude product was dissolved in methanol, and ice was added; the resulting precipitate was collected by filtration (Yield: 30e60%).

  • 2
  • [ 859855-53-1 ]
  • [ 140-89-6 ]
  • [ 149367-90-8 ]
YieldReaction ConditionsOperation in experiment
76% In N,N-dimethyl-formamide; at 110 - 120℃; S-Cyano-^-mercaptobenzothiazole (14): A mixture of 3-amino-4-chloro benzonitrile (13, 0.50 g, 3.28 mmol) and potassium O-ethyl dithiocarbonate (1.05 g, 6.55 mmol) in DMF (15 mL) was heated overnight at 110-120 0C under N2. After cooling, the reaction mixture was diluted with water and acidified with IN HCl. The precipitate was collected by filtration, washed with water, and dried under vacuum to yield 14 (0.48 g, 76%).
  • 3
  • [ 859855-53-1 ]
  • [ 75-36-5 ]
  • [ 939999-17-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 0.5h; N-(5-Cyano-2-fluoro-phenyl)-acetamide 10 mmol of <strong>[859855-53-1]3-Amino-4-fluoro-benzonitrile</strong> were dissolved in 30 ml THF. 1.5 eq of DIPEA were added and the reaction mixture cooled to 0 C. 1.2 eq of acetylchloride were added dropwise, the reaction warmed up to rt and stirred for additional 30 min. The solvent was evaporated and the product isolated via extraction from ethylacetate and saturated NaHCO3 solution. MS(ISO): 179.2 (MH+)
  • 4
  • [ 859855-53-1 ]
  • [ 1204572-73-5 ]
  • 5
  • [ 859855-53-1 ]
  • [ 1262338-81-7 ]
  • 6
  • [ 859855-53-1 ]
  • [ 1262337-56-3 ]
  • 9
  • [ 859855-53-1 ]
  • [ 1262338-80-6 ]
YieldReaction ConditionsOperation in experiment
80% Intermediate 2: [2-Fluoro-5-(lH-tetrazol-5-yl)phenyl] amine hydrochloride; A solution of 3-amino-4-fluoro-benzonitrile (Intermediate 1; 2.0 g; 14.7 mmol) in dry toluene (75 ml) was treated with sodium azide (2.86 g; 44 mmol) and triethylamine hydrochloride (6.0 g) and the mixture was refluxed for 24 h under nitrogen. The reaction mass was cooled and water (25 ml) was added to it. The aqueous phase was separated and acidified with an aqueous (6 N) HCl solution till pH=2. A solid precipitated, which was filtered, washed with cold water and dried under suction to afford the Title compound (2.5 g, 80%) as a solid.1H NMR (300MHz, DMSOd6) delta [ppm] 7.75-7.70 (m, IH), 7.53-7.52 (m, IH), 7.33-7.28 (m, IH), 5.56 (bs, 2H). MS (ESI+): 179.9. HPLC (Condition B): Rt 4.47 min (HPLC purity 99.8%).
  • 10
  • [ 859855-53-1 ]
  • [ 29668-44-8 ]
  • [ 1262338-85-1 ]
YieldReaction ConditionsOperation in experiment
Intermediate 8: 3-[(2,3-dihydro-l,4-benzodioxin-6-ylmethyl)amino]-4-fluorobenzonitrile; A suspension of 1 ,4-benzodioxan-6-carboxaldehyde (ABCR; 1.03 g; 6.27 mmol) and 3-amino-4- fluorobenzonitrile (Intermediate 1; 997 mg; 7.32 mmol) in Toluene (100 ml) was treated with p- toluenesulphonic acid monohydrate (10 mg; 0.06 mmol). A Dean-Stark trap was added and the suspension heated at reflux during 20 h, after which the reaction solution was cooled and concentrated to give a yellow solid. This was dissolved in MeOH (100 ml) and DCM (300 ml). The solution was cooled to -10 0C then treated with three portions OfNaBH4 (441 mg; 11.7 mmol each, 20 minutes apart). After stirring at room temperature for 3 h, the solution was concentrated then dissolved in DCM and washed with aqueous HCl (1 N). The layers were separated and the organic layer dried on MgSO4 and concentrated to give the Title compound (1.88 g, 90%) as an orange oil, which was used without further purification.1H NMR (300MHz, DMSOd6) delta [ppm] 7.27-7.16 (m, IH), 7.02-6.93 (m, 2H), 6.90-6.68 (m, 4H), 4.25 (d, J= 6.3 Hz, 2H), 4.20 (s, 4H). HPFC (Condition A): Rt 4.04 min (HPFC purity 89.2%).
  • 11
  • [ 859855-53-1 ]
  • [ 1350660-03-5 ]
  • [ 1350730-07-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; for 48h; Example 8: 4-Fluoro-3-[5-(3-morpholin-4-ylphenoxy)-pyrimidin-2-ylamino]- benzonitrileA suspension of 4-[3-(2-chloro-pyrimidin-5-yloxy)phenyl]morpholine (180mg, 0.619mmol), <strong>[859855-53-1]3-amino-4-fluorobenzonitrile</strong> (75.8mg, 0.557mmol), ira(dibenzylidene- acetone)palladium(O) (28.3mg, 0.030mmol), 4,5-bis,(diphenylphosphino)-9,9- dimethylxanthene (35.8mg, 0.061mmol) and cesium carbonate (403mg, 1.238mmol) in degassed 1,4-dioxane (4mL) was heated at 80C for 2 days. The suspension was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (ethyl acetate:hexane, 1: 1) to afford 4-fluoro-3-[5-(3-morpholin-4-ylphenoxy)-pyrimidin-2-ylamino]-benzonitrile as colourless oil (l l lmg, 46%). Mass: (ES+) 392 (M+H)+ HPLC: 94.1%NMR: 5H (d6-DMSO) 3.08 (4H, m), 3.69 (4H, m), 6.38 (1H, dd), 6.61 (1H, br s), 6.70 (1H, dd), 7.18 (1H, t), 7.47 (1H, t), 7.59 (1H, m), 8.40 (2H, s), 8.43 (1H, m) and 9.55 (1H, s).
  • 12
  • [ 859855-53-1 ]
  • [ 1262338-85-1 ]
  • 13
  • [ 859855-53-1 ]
  • [ 29668-44-8 ]
  • C16H11FN2O2 [ No CAS ]
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; ;