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Chemical Structure| 85068-29-7 Chemical Structure| 85068-29-7

Structure of 85068-29-7

Chemical Structure| 85068-29-7

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Product Details of [ 85068-29-7 ]

CAS No. :85068-29-7
Formula : C9H7F6N
M.W : 243.15
SMILES Code : NCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
MDL No. :MFCD00009909
InChI Key :DHVHORCFFOSRBP-UHFFFAOYSA-N
Pubchem ID :521099

Safety of [ 85068-29-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501
Class:8
UN#:3259
Packing Group:

Computational Chemistry of [ 85068-29-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 3
Num. H-bond acceptors 7.0
Num. H-bond donors 1.0
Molar Refractivity 44.12
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.99
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.55
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

5.34
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.6
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.41

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.03
Solubility 0.225 mg/ml ; 0.000926 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.74
Solubility 0.439 mg/ml ; 0.0018 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.22
Solubility 0.0146 mg/ml ; 0.00006 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.97 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.46

Application In Synthesis of [ 85068-29-7 ]

* 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 [ 85068-29-7 ]

[ 85068-29-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 24310-36-9 ]
  • [ 85068-29-7 ]
  • [ 851045-75-5 ]
YieldReaction ConditionsOperation in experiment
Step 2. Preparation of (+/-) (3, 5-Bis-trifluoromethyl-benzyl)- [1- (toluene-4-sulfonyl)- 2,3, 4, 5-tetrahydro-1H-benzo [b] azepin-5-yl]-amine. A mixture of (+/-) 1- (Toluene-4-sulfonyl)-1, 2,3, 4-tetrahydro-benzo [b] azepin-5- one (500 mg, 1.58 mmol), 3,5-Bis (trifluoromethyl) benzylamine (423 mg, 1.74 mmol) and titanium (IV) isopropoxide (0.59 ml, 1.97 mmol) in diglyme (2 ml) is stirred at room temperature for 22 hours. The mixture is diluted with methanol (7 ml) and treated with sodium borohydride (90 mg, 2.37 mmol), then stirred at room temperature for 6 hours. The mixture is treated with 0. 1N aqueous NaOH (15 ml) and stirred for 10 minutes, then filtered. The filter cake is washed with 1: 1 ethanol : diethyl ether. The filtrate is diluted with water (70 ml) and extracted with ethyl acetate (2x30 ml). The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated to an oil. The oil is < purified by silica gel column chromatography (eluent, 15 % ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 543 (M+H).
  • 2
  • [ 85068-29-7 ]
  • [ 2972-52-3 ]
  • [ 188781-27-3 ]
YieldReaction ConditionsOperation in experiment
61% Example 40 2,4-DICHLORO-5-N-[3',5'-BIS(TRIFLUOROMETHYL)BENZYL]PYRIMIDINE-5-CARBOXAMIDE The title compound was prepared as described in Example 1, but employing 2,4-dichloropyrimidine-5-carbonylchloride (0.10 g, 0.40 mmol) and 3,5-bistrifluoromethylbenzylamine (0.10 g, 0.45 mmol) to give the compound in a 61% yield (0.12 g); m.p. 144-145 C.
  • 3
  • [ 47375-34-8 ]
  • [ 85068-29-7 ]
  • C27H32F6N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; General procedure: 3,5-Bis(trifluoromethyl)benzylamine (1.0 equiv., 0.125 mmol,30.5 mg) was added to a solution of Boc-AA-OH (AA Tyr, 1.0 equiv.,0.125 mmol, 42 mg for Tyr), HATU (1.0 equiv., 0.125 mmol, 47.5 mg),HOAc (1.0 equiv., 0.125 mmol, 17 mg) and DIEA (4.0 equiv.,0.500 mmol, 0.087 mL) in dry DMF (1.25 mL) at room temperature. Thereaction mixture was stirred for overnight (20 h) and then quenched with 0.5Maqueous solution of KHSO4 (5 mL). It was then extracted with DCM(3 15 mL). The combined organic part was subsequently washed withbrine, saturated sodium bicarbonate and again brine. Evaporation ofDCM under reduced pressure using rotary evaporator gave the crudeproduct in quantitative yield. The Boc group was removed by treating theproduct with 80% TFA in DCM for 1 h at room temperature [36] Removalof volatiles provided the unprotected bis(trifluoromethyl)benzylaminederivative of the respective single amino acid. Washing with 1:4 solutionsof ether and hexanes (3 10 mL) provided the final product in >80%yield with <95% (HPLC)
 

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