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Chemical Structure| 13534-99-1 Chemical Structure| 13534-99-1

Structure of 13534-99-1

Chemical Structure| 13534-99-1

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Product Details of [ 13534-99-1 ]

CAS No. :13534-99-1
Formula : C5H5BrN2
M.W : 173.01
SMILES Code : BrC1=CC=CN=C1N
MDL No. :MFCD03095187
InChI Key :RBCARPJOEUEZLS-UHFFFAOYSA-N
Pubchem ID :817700

Safety of [ 13534-99-1 ]

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

Computational Chemistry of [ 13534-99-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 36.34
TPSA ?

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

38.91 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.69
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

1.2
Log Po/w (WLOGP)?

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

1.43
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.

0.99
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

1.41
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.34

Water Solubility

Log S (ESOL):?

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

-2.22
Solubility 1.03 mg/ml ; 0.00597 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.

-1.61
Solubility 4.21 mg/ml ; 0.0243 mol/l
Class?

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

Very 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

-2.51
Solubility 0.531 mg/ml ; 0.00307 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

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.

-6.5 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)

1.42

Application In Synthesis of [ 13534-99-1 ]

* 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 [ 13534-99-1 ]

[ 13534-99-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 13534-99-1 ]
  • [ 141095-78-5 ]
  • [ 1232038-73-1 ]
YieldReaction ConditionsOperation in experiment
12.0% With potassium carbonate; In ethanol; at 75℃; for 4h; 3-Bromo-2-pyridinamine (0.504 g, 2.9 mmol) and K2CO3 (0.392 g, 2.84 mmol) were added to a solution of 2-bromo-l-(tetrahydro-2H-pyran-4-yl)ethanone (0.784 g, 3.8 mmol) in EtOH (10 ml). The r.m. was stirred at 75 0C for 4 h. and was then cooled to r.t. Subsequently, DCM was added and the solution was washed with a sat. aq. NaHCO3 solution. The organic layer was dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography over silicagel (eluent: mixtures of hexane: EtOAc (ratios: 15:1; 10:1; 5:1; 1 :1)). The desired fractions were collected and worked up. Yield 0.096 g of intermediate 7 (12.0 %).
  • 2
  • [ 13534-99-1 ]
  • [ 904326-92-7 ]
  • C11H10FN3 [ No CAS ]
  • 3
  • [ 13534-99-1 ]
  • [ 74-89-5 ]
  • [ 56291-51-1 ]
YieldReaction ConditionsOperation in experiment
70% With copper(ll) sulfate pentahydrate; In water; at 150℃; for 0.75h;Microwave irradiation; 2-Amino-3-bromo-pyridine (200 mg, 1.2 mmol) and copper sulfate pentahydrate (17 mg, 0.069 mmol, 0.06 eq.) was added to microwave vessel with 40% methylamine in H2O (2.14 ml). The reaction mixture was heated at 150 C for 45 min. The crude mixture was filtered through Celite, partitioned between saturated aqueous NaHCO3 and DCM, then extracted with DCM. The organic layer was dried with brine and anhydrous Na2SO4, filtered, evaporated to dryness under vacuum and purified on silica gel by column chromatography using solvent gradient from hexane to EtOAc to give the desired product was yellow solid (86 mg, 70%)
  • 4
  • [ 13534-99-1 ]
  • [ 188869-05-8 ]
  • tert-butyl 6-bromo-3,4-dihydroimidazo[1,2-a:5,4-c']dipyridin-2(1H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; at 140℃; for 1.5h;Microwave irradiation; To a 10-mL microwave reaction container, it is 2-amino-3-bromopyridine (0.10 g). 0.58mmol and tert-butyl 3-bromo-4-oxo piperidine- 1-carboxylate (0.16 g) After measuring 0.58mmol and adding 1,2-dimethoxyethane (2 mL), diisopropylethylamine (following, DIPEA) (75 mg, 0.58mmol) was added, and it agitated for 90 minutes at 140 degrees C using the microwave reaction apparatus. Flash silica gel column chromatography (only n-hexane - n-hexane / ethyl acetate = 34/66) refines the rough product produced by condensing a reaction mixture, tert-butyl 6-bromo-3,4-dihydroimidazo [1,2-a:5,4-c'] **********- 2(1H)-carboxylate (compound of the following and the reference example 2) (29 mg, 81 **mols) was obtained as a light yellow oily matter (14percent of yield).
  • 5
  • [ 13534-99-1 ]
  • [ 26346-85-0 ]
  • 8-bromo-2-(2,4-dimethylphenyl)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In isopropyl alcohol; at 75℃; for 72h; To a solution of 3-bromopyridin-2-amine (200 mg, 1.16 mmol) in 2-propanol (2.3 mL) was added 2-bromo- 1 -(2,4-dimethylphenyl)ethanone (315 mg, 1.39 mmol). The mixture wasstirred at 75 C for 72 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The crude residue was partitioned between DCM (50 mL) and saturated aqueous NaHCO3 solution (50 mL) and the two phases were separated. The aqueous layer was extracted with DCM (2 X 50 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The mixture obtained was purified by silica gelchromatography (iPrOAc / Heptane = 1: 9) to give the title compound (242 mg, 70%) as a pale yellow solid. ‘HNMR (400 IVIFIz, DMSO-d6) 8.12 (dd, J = 6.7, 1.1 Hz, 1H), 7.84-7.77 (m, 1H), 7.74 (s, 1H), 7.43 (dd, J = 7.3, 1.0 Hz, 1H), 7.13 - 7.06 (m, 2H), 6.66 (dd, J = 7.3, 6.7 Hz, 1H), 2.52 (s, 3H), 2.36 (s, 3H). LCMS M/Z (M+H) 301.
  • 6
  • [ 13534-99-1 ]
  • [ 1215310-75-0 ]
  • C14H10BrF3N2O2S [ No CAS ]
  • 7
  • [ 13534-99-1 ]
  • [ 887144-94-7 ]
  • [ 79456-30-7 ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate; In acetonitrile; at 75℃; for 6h;Schlenk technique; Inert atmosphere; General procedure: Experimental Procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Togni?s Reagent 2 (0.25 mmol, 1.0 equiv), free anilines 1 (0.75 mmol, 3.0 equiv), K2CO3 (0.375 mmol, 1.5 equiv) and CH3CN (1.5 mL). The reaction mixture was then stirred at 75 C for 6 h under an argon atmosphere. The reaction progress was monitored by TLC. After cooling to room temperature, the mixture was washed with water and extracted with CH2Cl2 three times, then washed with saturated NaCl solution. The combined organic layer was dried with anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (Elutent: petroleum ether-EtOAc) to give the pure product. The products were characterized by 1H NMR, 13C NMR, 19F NMR, GC -MS.
 

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Technical Information

Categories

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