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Structure of 1869-24-5

Chemical Structure| 1869-24-5

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Product Details of [ 1869-24-5 ]

CAS No. :1869-24-5
Formula : C7H6F3NO2S
M.W : 225.19
SMILES Code : O=S(C1=CC=CC=C1C(F)(F)F)(N)=O
MDL No. :MFCD00042420
InChI Key :AFFPZJFLSDVZBV-UHFFFAOYSA-N
Pubchem ID :2778018

Safety of [ 1869-24-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1869-24-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 2
Num. H-bond acceptors 6.0
Num. H-bond donors 1.0
Molar Refractivity 42.44
TPSA ?

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

68.54 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.09
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

1.36
Log Po/w (WLOGP)?

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

3.59
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.

1.4
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

1.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.69

Water Solubility

Log S (ESOL):?

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

-2.28
Solubility 1.19 mg/ml ; 0.00527 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.

-2.4
Solubility 0.893 mg/ml ; 0.00396 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

-2.86
Solubility 0.312 mg/ml ; 0.00139 mol/l
Class?

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

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

No
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.

-6.71 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

0.0
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)

1.83

Application In Synthesis of [ 1869-24-5 ]

* 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 [ 1869-24-5 ]

[ 1869-24-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1869-24-5 ]
  • [ 122-51-0 ]
  • [ 727-43-5 ]
  • 2
  • [ 1869-24-5 ]
  • [ 10191-60-3 ]
  • [ 104667-64-3 ]
  • 3
  • [ 1869-24-5 ]
  • [ 65-85-0 ]
  • N-Benzoyl-2-trifluoromethyl-benzenesulfonamide [ No CAS ]
  • 4
  • [ 2960-66-9 ]
  • [ 1869-24-5 ]
  • ethyl (E)-4-[(2-trifluoromethylphenylsulfonyl)imino]-2-butenoate [ No CAS ]
  • 5
  • [ 915701-01-8 ]
  • [ 1869-24-5 ]
  • 2-trifluoromethyl-<i>N</i>-[1-(3-trifluoromethyl-benzyl)-1<i>H</i>-indole-2-carbonyl]-benzenesulfonamide [ No CAS ]
  • 6
  • [ 1869-24-5 ]
  • 2-((S)-2-Oxo-pyrrolidin-3-yloxy)-1-(2-trifluoromethyl-benzenesulfonyl)-1,2,3,4-tetrahydro-pyridine-4-carboxylic acid ethyl ester [ No CAS ]
  • 7
  • [ 1869-24-5 ]
  • [ 104667-73-4 ]
  • 8
  • [ 204378-36-9 ]
  • [ 1869-24-5 ]
  • [ 204378-14-3 ]
YieldReaction ConditionsOperation in experiment
83.7% Synthesis Example 5 Synthesis of N-[(2-Trifluoromethylphenyl)sulfonyl]-5-methoxy-2-pyridinecarboxamide [Compound (I-54)] Using <strong>[1869-24-5]2-trifluoromethylbenzenesulfonamide</strong> [Compound (III-1)] (0.197 g, 0.87 mmol) and 5-methoxypicolinic acid phenyl ester [Compound (IV-54)] (0.2 g, 0.87 mmol), the Compound (I-54) was synthesised according to the process of Synthesis Example 1. White solid, yield: 0.262 g, percent yield: 83.7%, m.p.: 153-156 C. IR KBr cm-1: 3340, 1722, 1587, 1422, 1398, 1359, 1311, 1272, 1188, 1149, 588, 561. 1H-NMR (60 MHz, CDCl3, delta): 3.80 (3H, s, OCH3), 7.16 (1H, dd, J=3 Hz, 9 Hz, pyridine ring H), 7.46-7.80 (3H, m, aromatic ring H), 7.9 (1H, d, J=9 Hz, pyridine ring H), 8.13 (1H, d, J=3 Hz, pyridine ring H), 8.23-8.66 (1H, m, aromatic ring H), NH indistinctness.
  • 9
  • [ 776-04-5 ]
  • [ 1869-24-5 ]
YieldReaction ConditionsOperation in experiment
95.6% Synthesis Example 27 Synthesis of 2-Trifluoromethylbenzenesulfonamide [Compound (III-1)] Using 2-trifluoromethylbenzenesulfonyl chloride [Compound (XXII-1)] (5 g, 0.0204 mol), the Compound (III-1) was synthesised according to the process of Synthesis Example 26. White solid, m.p.: 186-187 C., yield: 4.4 g, percent yield: 95.6%. IR KBr cm-1: 3394, 3274, 1347, 1161, 1140. 1H-NMR (60 MHz, d6-DMSO, delta): 7.4-7.9 (5H, m, aromatic ring H*3, NH2), 7.9-8.4 (1H, m, aromatic ring H).
89% Intermediate 1 : 2-(trifluoiOmethyl)benzenesulfonamide (cf. Scheme 3, compound XXI)To a solution of 2-(trifluoromethyl)benzenesulfonyl chloride (5g; 20.44 mmol; 1.00 eq.) in anhydrous THF (5.00 ml) was added a solution of 71 ml Ammonia in Ethanol 2M under nitrogen at room temperature. The reaction mixture was shaken for 2Oh at room temperature. The solvent was evaporated and the residue redissolved in EtOAc(15OmL) and then washed with NH4Cl saturated aqueous solution (5OmL) and brine (5OmL). The organic layer was dried over MgSO4, filtered and the solvent evaporated to give the pure 2- (trifluoromethyl)benzenesulfonamide as a yellowish solid (4.6g, 89% yield, 98.6% HPLC purity). This compound was utilized as such for the next reaction.IH NMR (300MHz, CDCl3); 5.0 (m, 2H), 7.6 (m, 2H), 7.8 (m, IH), 8.3 (m, IH). MS(ESr): 224.1.
With ammonium hydroxide; In acetonitrile; at 0 - 20℃; for 1h;Inert atmosphere; General procedure: In a 50 ml RB flask, sulfonyl chloride (500 mg) was taken in acetonitrile (5 ml) and the solution was cooled to 0 deg. Cel. To this aqueous ammonia solution (1.5 ml) was added dropwise. RM was then stirred at RT for 1 hr. RM was evaporated to dryness and the residue was then trichirated with minimum water and suspension was filtered and solid was dried to get the sulfonamide as solid.
  • 10
  • 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
  • [ 1869-24-5 ]
  • [ 6674-22-2 ]
  • 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; water; acetonitrile; STR30 (by process (b)) At 20 C., 28.1 g (0.125 mol) of <strong>[1869-24-5]2-trifluoromethyl-benzenesulphonamide</strong> and a solution of 19 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) in 50 ml of acetonitrile are added in succession to a solution of 28.1 g (0.10 mol) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 300 ml of acetonitrile. The reaction mixture is stirred at 20 C. until a clear solution is obtained. The solution is then concentrated under water pump vacuum and the residue is admixed with water and methylene chloride (300 ml each) and acidified with 2N hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted once more with 100 ml of methylene chloride and the combined organic phases are dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is crystallized from isopropanol. 29.6 g (72% of theory) of 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 154 C. are obtained. By the methods of Examples 1, 2 and 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below. STR31
  • 11
  • [ 1869-24-5 ]
  • [ 598-21-0 ]
  • [ 1048660-71-4 ]
  • 12
  • [ 938-16-9 ]
  • [ 1869-24-5 ]
  • [ 1263313-47-8 ]
  • 13
  • [ 1869-24-5 ]
  • [ 1152875-12-1 ]
  • 14
  • 4-(cyclopropylcarbamoyl)benzoic acid [ No CAS ]
  • [ 1869-24-5 ]
  • N<SUP>1</SUP>-cyclopropyl-N<SUP>4</SUP>-(2-(trifluoromethyl)phenylsulfonyl)terephthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetonitrile; at 20℃; for 24h; General procedure: To a stirred solution of 3I-3III (10 mmol) and Et3N (12 mmol) in anhydrous acetonitrile was added sulfamide (4a-i and 5, 10 mmol) followed by addition EDCI (12 mmol) and DMAP (12 mmol). The mixture was stirred at r.t. for 24 h. The reaction mixture was concentrated, and the residue was dissolved in dichloromethane. The organic layer was washed with 1N HCl and water for 3 times respectively, dried over anhydrous Na2SO4 and evaporated in vacuum. The residue was subjected to silica gel chromatography or crystallization.
  • 15
  • [ 1869-24-5 ]
  • 2-trifluoromethylbenzenesulfonamide-6-d<SUB>1</SUB> [ No CAS ]
  • 16
  • [ 5944-41-2 ]
  • [ 1869-24-5 ]
  • N-(2-methyl-2-(pyridin-2-yl)propyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • 17
  • [ 611-32-5 ]
  • [ 1869-24-5 ]
  • N-(quinolin-8-ylmethyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; sodium acetate; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Schlenk technique; General procedure: A Schlenk tube with a magnetic stir bar was charged with [RhCp*Cl2]2 (7.8 mg, 12.5 mumol), AgSbF6 (17.2 mg, 50 mumol), PhI(OAc)2 (120.4 mg, 0.375 mmol), NaOAc (6.2mg, 75 mumol), 8-methylquinoline derivative 1 (0.50 mmol), amide 2 (0.25 mmol), and DCM (1.0 mL) under an N2 atmosphere. The resulting mixture was stirred at room temperature for 48 h and then diluted with 3 mL of dichloromethane. The solution was filtered through a celite pad and washed with 10-20 mL of dichloromethane. The filtrate was concentrated and the residue was purified by column chromatography on silica gel to provide the desired product.
  • 18
  • [ 1869-24-5 ]
  • [ 68790-38-5 ]
  • tert-butyl(2-(((2-(trifluoromethyl)phenyl)sulfonyl)carbamoyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% General procedure: All solid chemicals used were dried in vacuum over P2O5 overnight.The acid derivative and CDI were dissolved in dry THF underN2 atmosphere and the mixture was allowed to stir at 66-68 C for2 h. The sulfonamide and DBU dissolved in THF were added to thereaction mixture and stirring was continued at room temperature(4 h-overnight).Method B1: The solvent was removed in vacuo, water was addedand pH was adjusted to 2 by addition of 1 M HCl aq. The aqueousphase was extracted with EtOAc (2 40 ml), dried with MgSO4, filteredand evaporated in vacuo. For most of the compounds, a silicagel column was first run, followed by purification on aluminumoxide.
  • 19
  • [ 1869-24-5 ]
  • 2-(2-(3-(3-(tert-butyl)ureido)-5-chloro-6-(2-cyclohexylethyl)-2-oxopyrazin-1(2H)-yl)acetamido)-N-((2-(trifluoromethyl)phenyl)sulfonyl)benzamide [ No CAS ]
  • 20
  • [ 1869-24-5 ]
  • C14H11F3N2O3S*ClH [ No CAS ]
  • 21
  • [ 1869-24-5 ]
  • [ 14790-72-8 ]
  • (4E,7E)-1,5,9,9-tetramethyl-12-((2-(trifluoromethyl)phenyl)sulfonyl)-12-azabicyclo[9.1.0]dodeca-4,7-dien-6-one [ No CAS ]
  • 22
  • [ 627-27-0 ]
  • [ 1869-24-5 ]
  • 2-(1,1-difluoro-5-hydroxypentyl)benzenesulfonamide [ No CAS ]
  • 23
  • [ 13333-97-6 ]
  • [ 1869-24-5 ]
  • 24
  • [ 1869-24-5 ]
  • [ 24195-03-7 ]
  • methyl 2-(((2-(trifluoromethyl)phenyl)sulfonyl)carbamoyl)isonicotinate [ No CAS ]
  • 25
  • [ 67-56-1 ]
  • [ 1869-24-5 ]
  • [ 4105-21-9 ]
  • N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium permanganate; di-tert-butyl peroxide; sodium t-butanolate; at 130℃; for 8h; The preparation method comprises the following steps: adding 0.1 mmol of 2-phenylimidazo[1,2-a]pyridine compound to a 35 mL high pressure tube under an air atmosphere.0.2 mmol of <strong>[1869-24-5]2-(trifluoromethyl)benzenesulfonamide</strong>,0.2 mmol of di-tert-butyl peroxide, 0.1 mmolPotassium permanganate, 0.1 mmol of sodium t-butoxide, hexafluoroisopropanol and methanol (volume ratio 1:9) 2 mL, reacted at 130 C for 8 hours;After completion, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to100/0), dried to a yellow solid, yield 84%.
  • 26
  • [ 1869-24-5 ]
  • N-(5-(tert-butyl)isoxazol-3-yl)-N-methyl-3-phenylpropiolamide [ No CAS ]
  • N-((E)-(2-((Z)-2-hydroxy-3,3-dimethylbut-1-en-1-yl)-1-methyl-5-oxo-1,5-dihydro-4H-imidazol-4-ylidene)(phenyl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • 27
  • [ 7342-82-7 ]
  • [ 1869-24-5 ]
  • N-(benzo[b]thiophen-3-yl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • 28
  • [ 1869-24-5 ]
  • C26H18F3NO3S2 [ No CAS ]
  • 29
  • [ 1869-24-5 ]
  • C21H12F6N2O2S2 [ No CAS ]
  • 30
  • [ 1869-24-5 ]
  • C26H17F3N2O2S2 [ No CAS ]
  • 31
  • [ 1869-24-5 ]
  • C22H18F3N3O2S2 [ No CAS ]
  • 32
  • [ 1869-24-5 ]
  • C24H18F3NO4S2 [ No CAS ]
  • 33
  • [ 1869-24-5 ]
  • C27H22F3N3O3S2 [ No CAS ]
  • 34
  • [ 1869-24-5 ]
  • C21H14F3NO5S2 [ No CAS ]
  • 35
  • [ 1869-24-5 ]
  • C20H14F3N3O3S2 [ No CAS ]
 

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