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Structure of 51618-30-5

Chemical Structure| 51618-30-5

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Product Details of [ 51618-30-5 ]

CAS No. :51618-30-5
Formula : C7H4BrNS2
M.W : 246.15
SMILES Code : S=C1SC2=CC(Br)=CC=C2N1
MDL No. :MFCD09880848
InChI Key :KNFZKHAWHVYFFI-UHFFFAOYSA-N
Pubchem ID :11322553

Safety of [ 51618-30-5 ]

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

Computational Chemistry of [ 51618-30-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 54.71
TPSA ?

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

76.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.07
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

3.1
Log Po/w (WLOGP)?

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

3.72
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.

2.18
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

5.42
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.3

Water Solubility

Log S (ESOL):?

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

-3.92
Solubility 0.0293 mg/ml ; 0.000119 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.

-4.37
Solubility 0.0106 mg/ml ; 0.000043 mol/l
Class?

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

Moderately 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

-3.94
Solubility 0.0284 mg/ml ; 0.000115 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

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

Yes
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

Yes
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.

-5.6 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

1.0 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)

2.38

Application In Synthesis of [ 51618-30-5 ]

* 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 [ 51618-30-5 ]

[ 51618-30-5 ] Synthesis Path-Downstream   1~20

YieldReaction ConditionsOperation in experiment
100% In ethanol;Reflux; General procedure: a) 6-Fluoro-benzooxazole-2-thiol (1a) 2-amino-5-fluoro-phenol (10 g, 79 mmol) is placed in the presence of potassium O-ethylcarbonodithioate (27.7 g, 173 mmol) in 100 mL of ethanol at reflux overnight. After reduction to dryness the residue is triturated in a solution of HCl 1N, filtered and then rinsed with HCl 1N. After drying under vacuum, 13.8 g of a brown solid is isolated (quantitative yield).
  • 2
  • [ 28563-38-4 ]
  • [ 367-24-8 ]
  • [ 51618-30-5 ]
  • 3
  • [ 51618-30-5 ]
  • [ 80945-86-4 ]
YieldReaction ConditionsOperation in experiment
96% General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20-25 C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20-25 C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.
  • 4
  • [ 367-24-8 ]
  • [ 140-89-6 ]
  • [ 51618-30-5 ]
  • 5
  • [ 615-57-6 ]
  • [ 51618-30-5 ]
YieldReaction ConditionsOperation in experiment
With carbon disulfide; sodium methylate; In N-methyl-acetamide; water; (a) 205 g of carbon disulfide are added dropwise to a stirred suspension of 135 g of sodium methylate in 1.3 l of dimethylformamide, under a nitrogen atmosphere. During this addition, the temperature of the reaction mixture rises to about 70 C. A solution of 288 g of 2,4-dibromoaniline in 300 ml of dimethylformamide is added dropwise at an internal temperature of 70-80 C. in the course of about 30-60 minutes. Thereafter, the internal temperature is increased to 100, with good reflux cooling, and is maintained at this level for about 14 hours, and the reaction mixture is then cooled, stirred into 6 l of water and acidified. The 6-bromo-2-mercaptobenzothiazole which precipitates is filtered off and washed with water. After drying in vacuo, 272 g (96.3% of theory, relative to the 2,4-dibromoaniline employed) of 6-bromo-2-mercaptobenzothiazole are obtained in a purity sufficient for further reactions. A purified sample had a melting point of 278.
  • 6
  • [ 600-00-0 ]
  • [ 51618-30-5 ]
  • [ 1192214-96-2 ]
  • 7
  • [ 51618-30-5 ]
  • [ 535-11-5 ]
  • [ 1192215-03-4 ]
  • 8
  • [ 75-15-0 ]
  • [ 615-57-6 ]
  • [ 51618-30-5 ]
  • 9
  • [ 52462-29-0 ]
  • [ 51618-30-5 ]
  • [Ru(η6-cymene)Cl2(6-bromo-2-mercaptobenzothiazole)] [ No CAS ]
  • 10
  • [ 66416-72-6 ]
  • [ 140-89-6 ]
  • [ 51618-30-5 ]
YieldReaction ConditionsOperation in experiment
78.7% With copper(l) chloride; In N,N-dimethyl-formamide; at 110℃; for 6h;Inert atmosphere; Sealed tube; General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).
72% With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In N,N-dimethyl-formamide; at 110℃; for 18h;Inert atmosphere; Sealed tube; General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.
  • 11
  • [ 615-57-6 ]
  • [ 140-89-6 ]
  • [ 51618-30-5 ]
YieldReaction ConditionsOperation in experiment
97.3% With copper(l) chloride; In N,N-dimethyl-formamide; at 110℃; for 6h;Inert atmosphere; Sealed tube; General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).
80% In N,N-dimethyl-formamide; at 120 - 130℃;Inert atmosphere; General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5-1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120-130 C until the aniline was fully consumed (3-14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1-2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.
  • 12
  • (difluoromethyl)triphenylphosphonium trifluoromethanesulfonate [ No CAS ]
  • [ 51618-30-5 ]
  • 6-bromo-2-((difluoromethyl)thio)benzo[d]thiazole [ No CAS ]
  • 13
  • [ 182499-80-5 ]
  • [ 75-15-0 ]
  • [ 10544-50-0 ]
  • [ 51618-30-5 ]
  • 14
  • [ 182499-80-5 ]
  • [ 75-15-0 ]
  • [ 51618-30-5 ]
YieldReaction ConditionsOperation in experiment
84.6% With sodium hydrogen sulfide; In water; at 80℃; for 4h;Green chemistry; Reaction flask was added 163mg (0.40mmol) of 4,4'-dibromo-2,2'-dithiodiphenylamine and 11.2mg (0.2mmol) of NaHS, was added 2.5mL H2O as the reaction solvent, re-injected into the carbon disulfide 97muL (1.6mmol), the mixture was stirred at 80 deg.] C for 4 hours, starting material disulfide plate chromatography testing found the reaction was complete, cooled to room temperature, extracted with ethyl acetate, and then after using a rotary evaporator the solvent was removed under reduced pressure to give the crude product.The crude product was dichloromethane as the eluent, using a gradient elution by column chromatography (silica gel 200-300 mesh), a purity of greater than 99% to give a white powder of 6-bromo-2-mercaptobenzimidazole and thiazole 166mg, isolated yield 84.6%, mp 265-266 .
  • 15
  • cyclobutanone O-benzoyl oxime [ No CAS ]
  • [ 51618-30-5 ]
  • 4-((6-bromobenzo[d]thiazol-2-yl)thio)butanenitrile [ No CAS ]
  • 16
  • cyclobutanone O-benzoyl oxime [ No CAS ]
  • [ 51618-30-5 ]
  • S-(6-bromobenzo[d]thiazol-2-yl)-N-cyclobutylidenethiohydroxylamine [ No CAS ]
  • 17
  • 2-benzylcyclobutan-1-one O-benzoyl oxime [ No CAS ]
  • [ 51618-30-5 ]
  • 4-((6-bromobenzo[d]thiazol-2-yl)thio)-5-phenylpentanenitrile [ No CAS ]
  • 18
  • [ 53218-26-1 ]
  • [ 51618-30-5 ]
YieldReaction ConditionsOperation in experiment
75% With 1.3-propanedithiol; dimethyl sulfoxide; potassium hydroxide; at 130℃; for 12h;Inert atmosphere; General procedure: To a solution of benzothiazoles or benzoxazoles (1, 1 mmol) in DMSO (3 mL), was added KOH (280 mg, 5 equiv) and 1,3-propanedithiol (207 muL, 2 mmol). The reaction mixture was heated under argon at 130 C for 12 h. After cooling to room temperature, water (10 mL) was added. The pH of the reaction mixture was adjusted to 3-4 using 5% HCl. The resulting mixture was extracted with ethyl acetate (15 mL ×2). The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated using rotary evaporator. The crude product was purified by silica gel column chromatography using ethyl acetate/n-hexane as eluent to afford the corresponding heteroaryl thiols 3.
  • 19
  • [ 110-89-4 ]
  • [ 51618-30-5 ]
  • [ 863001-19-8 ]
  • 20
  • C14H12I(1+)*CF3O3S(1-) [ No CAS ]
  • [ 51618-30-5 ]
  • (R)-6-bromo-2-((2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)thio)benzo[d]thiazole [ No CAS ]
 

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