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Chemical Structure| 73870-24-3 Chemical Structure| 73870-24-3

Structure of 73870-24-3

Chemical Structure| 73870-24-3

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Product Details of [ 73870-24-3 ]

CAS No. :73870-24-3
Formula : C6H7Br2N
M.W : 252.93
SMILES Code : BrCC1=CC=NC=C1.[H]Br
MDL No. :MFCD01863545
InChI Key :VAJUUDUWDNCECT-UHFFFAOYSA-N
Pubchem ID :12752219

Safety of [ 73870-24-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 73870-24-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 47.11
TPSA ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

2.47
Log Po/w (WLOGP)?

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

2.78
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.

1.8
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

2.4
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.89

Water Solubility

Log S (ESOL):?

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

-3.39
Solubility 0.103 mg/ml ; 0.000406 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.

-2.39
Solubility 1.04 mg/ml ; 0.00412 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

-3.28
Solubility 0.134 mg/ml ; 0.00053 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.

-6.09 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

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<0.0
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)

1.55

Application In Synthesis of [ 73870-24-3 ]

* 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 [ 73870-24-3 ]

[ 73870-24-3 ] Synthesis Path-Downstream   1~4

  • 2
  • [ 73870-24-3 ]
  • [ 851983-85-2 ]
  • 3β-(pyridine-4-ylmethoxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Sodium hydride {3.0 g, 125 mmol, 10 eq. (5.0 g of 60percent> NaH in oil)} was added to a solution of galeterone (1, 5.0 g, 12.9 mmoL, 1 eq.) in THF (80 mL) at 0°C under argon atmosphere. A white precipitate formed and after stirring for one minute, DMF (5.0 mL) was added and the reaction mixture was allowed to stir for 10 minutes at room temperature. The reaction mixture was placed at 0°C and lithium carbonate (5.0 g, 67.7 mmoL, 5 eq. ) was added, followed immediately by 4-(bromomethyl)pyridine hydrobromide (14, 10 g, 39.5 mmoL, 3 eq.) and the reaction mixture was allowed to stir at 0°C for 30 minutes. The reaction mixture was removed from 0°C and stirring continued at ambient temperature for 18 hours under argon atmosphere. The color of the reaction mixture changed from clear to dark red during the 18-hour period. After 18 hours, the reaction mixture was placed at 0°C, water (30 mL) was added to quench unreacted NaH, and the mixture was stirred for 10 minute. Volatile (THF) were removed in vacuo and water (70 mL) was added to the residue aqueous phase. The aqueous phase was extracted with ethyl acetate (EtOAc) (150 mL x 3). Ethyl acetate extract was washed with brine (80 mL x 2), dried with anhydrous Na2SO4 and concentrated in vacuo to give a dark red crude product. Purification by flash chromatography using 3percent MeOH/EtOAc as eluent afforded compound galeterone 3beta-pyridine methoxylate (3) as a white solid (3.78 g, 7.88 mmoL, 61percent), mp 177-179°C. Rf= 0.31 (5percent MeOH/EtOAc).
12% With sodium hydride; In N,N-dimethyl-formamide; at 65℃; for 12h;Inert atmosphere; To a solution of VN124-1 (0.1 g, 0.257 mmol), Sodium hydride (0.185 g, 7.7 mmol) and DMF (2 mL) at room temperature under argon added 4-(bromomethyl)pyridine hydrobromide (0.2 g, 0.772 mmol). The reaction heated to 65 °C, continued for 12 hr, cooled and then poured onto ice cold water, filtered and dried. Purification by FCC [petroleum ether/EtOAc (3:2)] gave VNPP414(A16) (15 mg, 12 percent): mp 166-67 °C; NMR (400 MHz, CDC13) delta 1.02 (s, 3 H, I8-CH3), 1.08 (s, 3 H, 19-CH3), 3.30 (m, 1 H, 3 -H), 4.59 ( s, 2 H, -CH2), 5.42 (d, J=4.89 Hz, 1 H, 6-H), 5.98 (br. s., 1 H, 16-H), 7.27 - 7.34 (m, 4 H, aromatic-Hs), 7.49 (d, J=5.14 Hz, 1 H, Ar7 FontWeight="Bold" FontSize="10" -H), 7.81 (d, J=4.40 Hz, 1 H, Ar- 6 FontWeight="Bold" FontSize="10" -H), 7.95 ( s, 1 H, Ar^'-H), 8.57 (d, J=4.65 Hz, 2 H, Ar-22, 62-Hs); 13C NMR (101 MHz, CDC13) 5 149.8, 148.2, 141.6, 141.0, 134.5, 124.0, 123.3, 122.4, 121.7, 121.2, 120.2, 111.1, 79.1, 68.3, 55.9, 50.5, 47.2, 39.1, 37.1, 37.0, 34.8, 31.1, 30.3, 30.3, 28.3, 20.6, 19.3, 16.0; HRMS calcd 502.2828 (C32H37N30)Na+, found 502.2834.
  • 3
  • [ 42726-73-8 ]
  • [ 73870-24-3 ]
  • 1-tert-butyl 3-methyl 2-pyridin-4-ylmethylmalonate [ No CAS ]
  • 4
  • [ 42726-73-8 ]
  • [ 73870-24-3 ]
  • 1-tert-butyl 3-methyl 2-benzoyloxy-2-pyridin-4-ylmethylmalonate [ No CAS ]
  • 1-tert-butyl 3-methyl 2-benzoyloxy-2-pyridin-4-ylmethylmalonate [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 73870-24-3 ]

Bromides

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2-Bromo-4-(bromomethyl)pyridine hydrobromide

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A186384 [1384972-83-1]

3-(Bromomethyl)-4-methylpyridine hydrobromide

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Related Parent Nucleus of
[ 73870-24-3 ]

Pyridines

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2-Bromo-4-(bromomethyl)pyridine

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2-Bromo-4-(bromomethyl)pyridine hydrobromide

Similarity: 0.90

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A186384 [1384972-83-1]

3-(Bromomethyl)-4-methylpyridine hydrobromide

Similarity: 0.89

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A298751 [4926-28-7]

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Similarity: 0.85

Chemical Structure| 120277-01-2

A411963 [120277-01-2]

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Similarity: 0.85