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[ CAS No. 851386-33-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 851386-33-9
Chemical Structure| 851386-33-9
Chemical Structure| 851386-33-9
Structure of 851386-33-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 851386-33-9 ]

CAS No. :851386-33-9 MDL No. :MFCD09031171
Formula : C6H3F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DGNBUWVYFMVMHG-UHFFFAOYSA-N
M.W : 159.09 Pubchem ID :11457834
Synonyms :

Calculated chemistry of [ 851386-33-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.11
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.03
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : -0.24
Log Po/w (SILICOS-IT) : 1.6
Consensus Log Po/w : 1.04

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.74
Solubility : 2.91 mg/ml ; 0.0183 mol/l
Class : Very soluble
Log S (Ali) : -1.55
Solubility : 4.49 mg/ml ; 0.0282 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.95
Solubility : 1.81 mg/ml ; 0.0114 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 851386-33-9 ]

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 [ 851386-33-9 ]

* 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 [ 851386-33-9 ]

[ 851386-33-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 683242-79-7 ]
  • [ 851386-33-9 ]
  • [ 1375702-93-4 ]
YieldReaction ConditionsOperation in experiment
Step 3: To a solution of <strong>[851386-33-9]5,6-difluoropyridine-3-carboxylic acid</strong> (348mg, 2.19mmol) in dry NMP(3mL) was added l-hydroxybenzotriazole (335mg, 2.19mmol),and iV-[3- (dimethylamino)propyl3-N'-ethyicarbodiimide hydrochloride (420mg> 2.19mmol). The mixture was stirred for 10 min. and 6-(trifluoromethyl)pyridine-2, 3 -diamine (388mg, 2.19mmol) was added. The mixture was stirred at RT for 16 hours. Acetic acid (2mL) was added and the mixture was heated to 120 C for 60 min. in a microwave. The cooled mixture was partitioned between ethyl acetate and sodium bicarbonate solution. The organic layer was dried over Na2S04 and concentrated. The mixture was purified by phase Prep HPLC using 10-100%CH3CN H2O/0.1 %TFA as gradient. The resulting mixture was treated with acetic acid at 120 C for 30 min. in a microwave. The acetic acid was evaporated and the residue was washed with toluene twice to give 2-(5,6-difluoropyridin-3-yl)-5-(trifluoromethyl)-3H-imidazo[4,5-¾]pyridine. LC-MS (M+H) = 301
  • 2
  • [ 851386-33-9 ]
  • [ 368-71-8 ]
  • [ 1370534-57-8 ]
YieldReaction ConditionsOperation in experiment
Step A: N-r2-amino-4-ftrifluoromethyl phenyl]-5,6-difluoropyridine-3-carboxai¾ide A solution of 4-(trifluoromethy)benzene-l ,2-diamine (980 mg, 5.56 mmol) in anhydrousDMF (20 ml) under nitrogen atmosphere was added <strong>[851386-33-9]5,6-difluoropyridine-3-carboxylic acid</strong> (590 mg, 3.71 mmol), EDC. HC1 (1066 mg, 5.56 mmol), and HOBT (852 mg, 5.56 mmol). DIEA was then added via a syringe and the mixture was stirred at room temperature over night. The reaction was quenched with water and washed with ethyl acetate (x2). The combined organic layers was then washed with brine, dried (NajSO.;) and filtered. The filtrate was concentrated under vacuum to afford a viscous oil. The resulting oil was then purified on the 1SCO CombiFlash Companion (with a 10 g Biotog Snap Column) eluting with 20 to 100 % ethylacetate / hexane gradient. The desired fractions were concentrated to afford the title compound as a tan solid. LC-MS (ES, m/z) C13H6CI2F3 3: 317; Found: 318 [M+l].
660 mg With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; A solution of 4-(trifiuoromethyl)benzene-l ,2-diamine (980 mg, 5.56 mmol) and 5,6- difluoronicotinic acid (590 mg, 3.71 mmol) in anhydrous DMF (20 ml) was treated with EDC (1066 mg, 5.56 mmol) and EtaOmicronBetaTau (852 mg, 5.56 mmol) in an N2 atmosphere. To the stirred solution was added DIEA (0.972 mL, 5.56 mmol) and the mixture stirred at room temperature overnight. The mixture was diluted with EtOAc and H20 and the layers separated. The organic phase was washed with H20 and brine, dried over Na2S04, filtered and evaporated to give 860 mg of a viscous oil. Purification on the CombiFlash Companion, on a 10 g column eluting with 20-100% EtOAc/ Hexane over 15 CV. to give 660 mg of N-(2-amino-4-(trifluoromethyl)phenyl)-5,6-difluoronicotinamide as a tan solid. LC-MS (M+l) = 318.
  • 3
  • [ 851386-33-9 ]
  • [ 1370534-58-9 ]
  • 4
  • [ 851386-33-9 ]
  • [ 1370534-56-7 ]
  • 5
  • [ 851386-33-9 ]
  • 3-fluoro-5-(6-(trifluoromethyl)-1H-benzo[b]imidazol-2-yl)pyridin-2-ol [ No CAS ]
  • 6
  • [ 851386-33-9 ]
  • 5-chloro-2-(piperazin-1-yl)oxazolo[4,5-b]pyridine hydrochloride [ No CAS ]
  • (4-(5-chlorooxazolo[4,5-b]pyridin-2-yl)piperazin-1-yl)(5,6-difluoropyridin-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-chloro-2-(piperazin-1-yl)oxazolo[4,5-b]pyridine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 5,6-difluoronicotinic acid In N,N-dimethyl-formamide at 20℃; for 17h; C.26 1-[(3-Chloro-5-iodophenyl)carbonyl]-4-{5-methyl-[1,3]oxazolo[4,5-b]pyridin-2- yl}piperazine General procedure: To a solution of 1-(5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-yl)piperazine, trifluoroacetic acid (550 mg, 1.66 mmol) in DMF (5 mL) was added triethylamine (0.92 mL, 6.62 mmol) and stirred for 10 minutes at r.t., followed by the addition of 3-chloro-5-iodobenzoic acid (468 mg, 1.66 mmol) and HATU (944 mg, 2.48 mmol). The mixture was then stirred for 17 h at the same temperature. The reaction mixture was diluted with EtOAc (50 mL), and water (50 mL). The solid part was filtered and washed with EtOAc and dried in vacuo providing the title compound (710 mg, 89%) as an off white solid. MS (ESI): m/z = 482.6 [M+H]+
  • 7
  • [ 851386-33-9 ]
  • 5-methyl-2-(piperazin-1-yl)oxazolo[4,5-b]pyridine [ No CAS ]
  • (5,6-difluoropyridin-3-yl)(4-(5-methyloxazolo[4,5-b]pyridin-2-yl)piperazin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methyl-2-(piperazin-1-yl)oxazolo[4,5-b]pyridine With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 5,6-difluoronicotinic acid In N,N-dimethyl-formamide at 20℃; for 17h; C.21 1-[(3-Chloro-5-iodophenyl)carbonyl]-4-{5-methyl-[1,3]oxazolo[4,5-b]pyridin-2- yl}piperazine General procedure: To a solution of 1-(5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-yl)piperazine, trifluoroacetic acid (550 mg, 1.66 mmol) in DMF (5 mL) was added triethylamine (0.92 mL, 6.62 mmol) and stirred for 10 minutes at r.t., followed by the addition of 3-chloro-5-iodobenzoic acid (468 mg, 1.66 mmol) and HATU (944 mg, 2.48 mmol). The mixture was then stirred for 17 h at the same temperature. The reaction mixture was diluted with EtOAc (50 mL), and water (50 mL). The solid part was filtered and washed with EtOAc and dried in vacuo providing the title compound (710 mg, 89%) as an off white solid. MS (ESI): m/z = 482.6 [M+H]+
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