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[ CAS No. 1065267-10-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1065267-10-8
Chemical Structure| 1065267-10-8
Chemical Structure| 1065267-10-8
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Product Details of [ 1065267-10-8 ]

CAS No. :1065267-10-8 MDL No. :MFCD11616885
Formula : C8H7F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VEXJJUULFRUNOQ-UHFFFAOYSA-N
M.W :187.14 Pubchem ID :46311358
Synonyms :

Calculated chemistry of [ 1065267-10-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.24
TPSA : 39.19 Ų

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 : No
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 1.61
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.3 mg/ml ; 0.00695 mol/l
Class : Soluble
Log S (Ali) : -2.04
Solubility : 1.69 mg/ml ; 0.00902 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.161 mg/ml ; 0.000859 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 1065267-10-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1065267-10-8 ]

* 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 [ 1065267-10-8 ]

[ 1065267-10-8 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 298709-29-2 ]
  • [ 64-17-5 ]
  • [ 1065267-10-8 ]
YieldReaction ConditionsOperation in experiment
69% 3,5-Difluoropyridine-2-carbonitrile (3.5g, 25mmol) was dissolved in EtOH (5OmL) and 4N HCl/l,4-dioxane (5OmL) was added. This reaction mixture was refiuxed for 24 hours under a nitrogen atmosphere. The reaction mixture was concentrated, dissolved in ethyl acetate (10OmL), and washed with saturated NaHCO3. The organic layer was dried over Na2SO4, and concentrated under reduced pressure. Purification by column chromatography (EtOAc : Hexanes = 1 :9) gave the title compound (3.1g, 69percent) as a semi solid. LCMS: [M+H]+188
  • 2
  • [ 1065267-10-8 ]
  • [ 1065267-14-2 ]
YieldReaction ConditionsOperation in experiment
98% With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 2h;Cooling with ice; Step B: Preparation of (3,5-difluoro-pyridin-2-yl)-methanol To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of Step A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0 C. for thirty minutes and at ambient temperature for two hours. The reaction was returned to 0 C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g, 98%). MS (M+H): 146
71% With lithium borohydride; In tetrahydrofuran; at 0 - 25℃; A stirred solution of ethyl 3,5-difluoropyridine-2-carboxylate (Intermediate 29, 3.1g, 16.57mmol) in anhydrous THF (10OmL) was cooled to O0C. To this solution was added portion- wise LiBH4 (l.lg, 50mmol) under a nitrogen atmosphere. After stirring 30 minutes at O0C, the reaction mixture was warmed to room temperature and stirred overnight. After cooling to O0C, the reaction mixture was quenched with MeOH, followed by saturated NH4Cl (aq) solution. After most of the organic solvent was removed by evaporation, the residue remaining was diluted with H2O and extracted with EtOAc (2x). The combined organic phases were dried (Na2SO4) and evaporated to give the title compound (1.7g, 71%). <n="75"/>LCMS: [M+H]+ 146.
  • 3
  • [ 1065267-10-8 ]
  • [ 1222633-85-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / Cooling with ice 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Cooling with ice
  • 4
  • [ 1065267-10-8 ]
  • [ 1442482-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / Cooling with ice 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Cooling with ice 3: potassium carbonate; 18-crown-6 ether / 18 h / 60 °C
  • 5
  • [ 1065267-10-8 ]
  • (+)-5-chloro-6-((3,5-difluoropyridin-2-yl)methoxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one [ No CAS ]
  • (-)-5-chloro-6-((3,5-difluoropyridin-2-yl)methoxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / Cooling with ice 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Cooling with ice 3: potassium carbonate; 18-crown-6 ether / 18 h / 60 °C 4: chiralcel OJ-H / isopropyl alcohol
  • 6
  • [ 745784-04-7 ]
  • [ 64-17-5 ]
  • [ 1065267-10-8 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; at 60℃; for 3h;Cooling with ice; Step A: Preparation of <strong>[745784-04-7]3,5-difluoro-pyridine-2-carboxylic acid</strong> ethyl ester To a suspension of <strong>[745784-04-7]3,5-difluoropyridine-2-carboxylic acid</strong> (2.0 g, 12.6 mmol) in ethanol (5 mL), cooled using an ice water bath, was added thionyl chloride (2 mL) in a dropwise manner. The solution was heated at 60 C. for three hours. The reaction was returned to ambient temperature and was concentrated in vacuo to provide the ethyl ester, hydrochloride salt, as a yellow oil (2.5 g, quantitative yield).
88% With sulfuric acid; at 80℃; for 2h; A solution of <strong>[745784-04-7]3,5-difluoropicolinic acid</strong> (3.3 g, 20.75 mmol), H2S04 (5 mL)in EtOH (20 mL) was stirred for 2 hours at 80 C. Then solvent was removed. The residue was diluted with EtOAc and it was washed with brine(x2). The organic layers was concentrated to give ethyl 3,5-difluoropicolinate as a pale yellow solid (3.44 g, 88%). ESI-MS m/z: 188.0 [M+Hjt
88% With sulfuric acid; at 80℃; for 2h; A solution of <strong>[745784-04-7]3,5-difluoropicolinic acid</strong> (3.3 g, 20.75 mmol), H2SO4 (5 mL)in EtOH (20 mL) was stirred for 2 hours at 80 oC. Then solvent was removed. The residue was diluted with EtOAc and it was washed with brine(x2). The organic layers was concentrated to give ethyl 3,5-difluoropicolinate as a pale yellow solid (3.44 g, 88%). ESI-MS m/z: 188.0 [M+H]+.
  • 7
  • [ 1065267-10-8 ]
  • 5-(2,2-difluoroethoxy)-3-fluoropyridine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 48 h / 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 120 h / 20 °C
  • 8
  • [ 359-13-7 ]
  • [ 1065267-10-8 ]
  • ethyl 5-(2,2-difluoroethoxy)-3-fluoropyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With potassium carbonate In acetonitrile at 20℃; for 48h; 30 PREPARATION 30 Ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylate Ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylate Ethyl 3,5-difluoropyridine-2-carboxylate (0.98 g, 5.24 mmol) is dissolved in acetonitrile (20 mL). Difluoroethanol (430 μL, 6.81 mmol) is added followed by potassium carbonate (1.83 g, 13.09 mmol). The solution is stirred at room temperature for 2 days then filtered and the filtrate is concentrated. The crude material is purified via silica gel chromatography eluting with a 0-25-50% ethyl acetate/hexanes gradient to give the title compound (242 mg, 18%). ES/MS (m/e): 250.0 (M+1).
  • 9
  • [ 110-91-8 ]
  • [ 1065267-10-8 ]
  • ethyl 5-fluoro-3-morpholinopicolinate [ No CAS ]
  • ethyl 3-fluoro-5-morpholinopicolinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; Overall yield = 3.37 g; 136.b Example 136 step b; A solution of ethyl 3,5-difluoropicolinate (3.1 g, 16.6 mmol), morpholine (1.44 g, 16.6 mmol) and K2C03 (6.87 g, 49.8 mmol) in DMF (4 mL) and DMSO (6 mL) was stirred for overnight at room temperature. It was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give a mixture of ethyl 5-fluoro-3-morpholinopicolinate and the isomer ethyl 3-fluoro-5-morpholinopicolinate as a pale yellow solid (3.37 g). ESI-MS m/z: 255.2 [M+Hf
With potassium carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; Overall yield = 3.37 g; 136.b A solution of ethyl 3,5-difluoropicolinate (3.1 g, 16.6 mmol), morpholine (1.44 g, 16.6 mmol) and K2CO3 (6.87 g, 49.8 mmol) in DMF (4 mL) and DMSO (6 mL) was stirred for overnight at room temperature. It was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give a mixture of ethyl 5-fluoro-3- morpholinopicolinate and the isomer ethyl 3-fluoro-5-morpholinopicolinate as a pale yellow solid (3.37 g). ESI-MS m/z: 255.2 [M+H]+.
  • 10
  • [ 1065267-10-8 ]
  • (S)-3-((5-(5-fluoro-3-morpholinopyridin-2-yl)-1,3,4-oxadiazol-2-yl)amino)-5-phenyl-1,3-dihydro-2H-benzo[e][1,4] diazepin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 4: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C 5: N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C 6: triethylamine; p-toluenesulfonyl chloride; dmap / dichloromethane / 1 h
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 1.2: 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: hydrogenchloride / water; ethyl acetate / 0.5 h / 20 °C 4.1: N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C 4.2: 48 h 5.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 1 h
  • 11
  • [ 1065267-10-8 ]
  • 5-fluoro-3-morpholinopicolinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C
  • 12
  • [ 1065267-10-8 ]
  • tert-butyl 2-(5-fluoro-3-morpholinopicolinoyl)hydrazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 1.2: 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C
  • 13
  • [ 1065267-10-8 ]
  • 5-fluoro-3-morpholinopicolinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 4: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 1.2: 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: hydrogenchloride / water; ethyl acetate / 0.5 h / 20 °C
  • 14
  • [ 1065267-10-8 ]
  • (S)-2-(5-fluoro-3-morpholinopicolinoyl)-N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)hydrazine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 4: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C 5: N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; dimethyl sulfoxide / 20 °C 1.2: 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: hydrogenchloride / water; ethyl acetate / 0.5 h / 20 °C 4.1: N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C 4.2: 48 h
  • 15
  • [ 110-91-8 ]
  • [ 1065267-10-8 ]
  • 5-fluoro-3-morpholinopicolinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
817 mg Stage #1: morpholine; 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester With potassium carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; 136.c A solution of ethyl 3,5-difluoropicolinate (3.1 g, 16.6 mmol), morpholine (1.44 g, 16.6 mmol) and K2CO3 (6.87 g, 49.8 mmol) in DMF (4 mL) and DMSO (6 mL) was stirred for overnight at room temperature. It was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give a mixture of ethyl 5-fluoro-3- morpholinopicolinate and the isomer ethyl 3-fluoro-5-morpholinopicolinate as a pale yellow solid (3.37 g). ESI-MS m/z: 255.2 [M+H]+. Example 136 step c: A solution of the mixture of isomers from step b (3.37 g, 13.3 mmol) and NaOH (796 mg, 19.9 mmol) in THF (10 mL) and H2O (15 mL) was stirred for 2 hours at room temperature. It was adjusted pH to 2-3 with HCl and purified by Prep-HPLC (MeCN/H2O) to give 817 mg of the desired compound 5-fluoro-3-morpholinopicolinic acid as a white solid. ESI-MS m/z: 227.0[M+H]+.
  • 16
  • [ 5308-25-8 ]
  • [ 1065267-10-8 ]
  • ethyl 5-(4-ethylpiperazin-1-yl)-3-fluoropyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.46 g With potassium carbonate In N,N-dimethyl acetamide at 70℃; for 2h; Microwave irradiation; Preparation of ethyl 5-(4-ethylpiperazin-1-yl)-3-fluoropyridine-2-carboxylate Preparation of ethyl 5-(4-ethylpiperazin-1-yl)-3-fluoropyridine-2-carboxylate In a microwave reactor, a suspension of 1.98 g (17.4 mmol) of 1-ethylpiperazine, 2.50 g (13.4 mmol) of ethyl 3,5-difluoropyridine-2-carboxylate and 2.40 g (17.4 mmol) of potassium carbonate in 21 ml of N,N-dimethylacetamide was heated at 70° C. for 2 h. Water was then added to the reaction mixture and the mixture was extracted repeatedly with ethyl acetate. The combined organic phases were dried with sodium sulfate and filtered and the solvent was removed under reduced pressure. The residue was separated chromatographically by MPLC on silica gel (gradient: cyclohexane/ethyl acetate+1% v/v triethylamine). This gave 1.46 g of ethyl 5-(4-ethylpiperazin-1-yl)-3-fluoropyridine-2-carboxylate. 1H-NMR (400.0 MHz, d6-DMSO): δ=8.2421 (2.7); 8.2374 (4.2); 7.2262 (2.2); 7.2203 (2.2); 7.1891 (2.2); 7.1832 (2.2); 4.2963 (2.2); 4.2786 (7.0); 4.2608 (7.1); 4.2431 (2.3); 3.4222 (6.1); 3.4097 (7.9); 3.3967 (6.4); 3.3230 (23.9); 2.9455 (4.4); 2.7859 (3.6); 2.5080 (21.5); 2.5036 (28.6); 2.4992 (21.7); 2.4833 (6.8); 2.4705 (8.4); 2.4579 (6.3); 2.3926 (1.9); 2.3746 (6.1); 2.3566 (6.2); 2.3387 (2.1); 1.9587 (3.8); 1.3048 (7.7); 1.2870 (16.0); 1.2693 (7.5); 1.0464 (6.7); 1.0284 (13.9); 1.0105 (6.4); 0.0079 (0.8); -0.0002 (18.1); -0.0082 (0.8).
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