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Structure of 20511-12-0

Chemical Structure| 20511-12-0

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Product Details of [ 20511-12-0 ]

CAS No. :20511-12-0
Formula : C5H5IN2
M.W : 220.01
SMILES Code : C1=C(C=NC(=C1)N)I
MDL No. :MFCD00160312
InChI Key :IVILGUFRMDBUEQ-UHFFFAOYSA-N
Pubchem ID :88579

Safety of [ 20511-12-0 ]

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

Computational Chemistry of [ 20511-12-0 ] 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 41.36
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.

1.39
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

1.31
Log Po/w (WLOGP)?

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

1.28
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.

1.16
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

1.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.37

Water Solubility

Log S (ESOL):?

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

-2.58
Solubility 0.573 mg/ml ; 0.0026 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.

-1.73
Solubility 4.12 mg/ml ; 0.0187 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

-2.62
Solubility 0.524 mg/ml ; 0.00238 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

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)

2.21

Application In Synthesis of [ 20511-12-0 ]

* 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 [ 20511-12-0 ]

[ 20511-12-0 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 20511-12-0 ]
  • [ 13472-79-2 ]
  • 2
  • [ 504-29-0 ]
  • [ 20511-12-0 ]
  • [ 23597-15-1 ]
  • 4
  • [ 504-29-0 ]
  • [ 1600-27-7 ]
  • [ 7553-56-2 ]
  • [ 20511-12-0 ]
  • [ 23597-15-1 ]
  • 5
  • [ 20511-12-0 ]
  • [ 13472-61-2 ]
  • 6
  • [ 20511-12-0 ]
  • [ 124-41-4 ]
  • [ 10167-97-2 ]
YieldReaction ConditionsOperation in experiment
31% With copper; In methanol; at 160℃; 2-Amino-5-methoxy-pyridine. A mixture OF 2-AMINO-5-IODO-PYRIDINE (1 g, 4.54 mmol) in 20 mL of absolute methanol with 400 mg of copper powder and sodium methoxide (6 mmol) was heated at 160 °C overnight in a seal tube. The reaction mixture was cooled to room temperature, diluted with 80 mL of methanol and filtered through a pad of celite. The filtrate was concentrated and the residue was purified by chromatography (80percent ethyl acetate/hexane) to give the title compound (174 mg, 31percent). 1H NMR (CDCl3) : 7.78 (d, J = 2.7, 1H), 7.09 (dd, J = 3.0, 9.0, 1H), 6.48 (d, J= 9.0, 1H), 3.78 (s, 3H).
  • 7
  • [ 20511-12-0 ]
  • [ 12775-96-1 ]
  • [ 10167-97-2 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; A. 2-Amino-5-methoxypyridine is prepared by combining 55 g. of 2-amino-5-iodopyridine, 20 g. of sodium methoxide, 5 g. of copper powder, 500 ml. of methanol in a glass lined bomb and rocking at 150° C. for 12 hours. Upon concentration to dryness, an extraction with chloroform extracts are dried and evaporated to dryness in vacuo. The residue is chromatographed on 1200 g. of silica gel eluding with 50percent ethylacetate and methylenechloride affording 2-amino-5-methoxy pyridine.
  • 8
  • [ 20511-12-0 ]
  • [ 134464-79-2 ]
  • [ 1231930-12-3 ]
YieldReaction ConditionsOperation in experiment
With magnesium; sodium t-butanolate;copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; In toluene; at 110℃; for 24h;Inert atmosphere; Sealed tube; Sonographic reaction; Preparation 14-(6-Amino-pyridin-3-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterAdd dry toluene (6.06 mL) to a mixture of 2,9-dimethyl-1,10-phenanthroline (76.52 mg), copper(I) iodide (69.27 mg), sodium tert-butoxide (475.59 mg), 4-mercapto-piperidine-1-carboxylic acid tert-butyl ester (583.5 mg), magnesium (49.10 mg) and 2-amino-5-iodopyridine (550 mg). Bubble nitrogen into the mixture with ultrasound and stir the suspension at 110 C. in a sealed tube for 24 h. Cool and filter through celite. Wash with toluene and remove the solvent under vacuum. Add hexane/EA (1/1) and filter through a celite/silica gel pad, washing twice with hexane/EA (1/1) and then EA. Remove the solvent under vacuum. Purify by silica gel column chromatography eluting with hexane/EA (50-75%) to afford 630 mg of the title compound. MS (ES+): m/z=310 (M+H)+
  • 9
  • [ 109-11-5 ]
  • [ 20511-12-0 ]
  • [ 1227486-41-0 ]
YieldReaction ConditionsOperation in experiment
100% With potassium phosphate; copper(l) iodide; In 1,4-dioxane; at 110℃; A solution of Example 149a (200 mg, 0.90 mmol), Example 149b (95 mg, 0.91 mmol), Example 149c (26 mg, 0.18 mmol), CuI (18 mg, 0.09 mmol) and K3PO4 (380 mg, 1.82 mmol) in 1,4- dioxane (5 mL) was stirred at 110oC overnight. The reaction was diluted with CH3CN (5 mL), filtered and concentrated to give the crude product Example 149d (210 mg, quant.) as black oil.1H NMR (400 MHz, DMSO-d6) d 7.85 (br, 1H), 7.33 (d, J = 8.0 Hz, 1H), 6.43 (d, J = 8.0 Hz, 1H), 5.98 (s, 2H), 4.13 (s, 2H), 3.91 (t, J = 4.0 Hz, 2H), 3.61 (t, J = 4.0 Hz, 2H).
With potassium phosphate;copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 110℃; for 23h; To a suspension of 5-iodopyridin-2-amine (800 mg) in dioxane (6 mL) were added copper (I) iodide (6.9 mg), trans-cyclohexane-1,2-diamine (44 μL), <strong>[109-11-5]morpholin-3-one</strong> (441 mg), and powdery tripotassium phosphate (1.54 g). The resulting reaction mixture was heated and stirred at 110C for 23 hours. After cooling to room temperature, the reaction mixture was filtered through celite, and the solid was washed with CHCl3. The liquid was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (CHCl3/MeOH = from 100/0 to 88/12) to obtain 4-(6-aminopyridin-3-yl)<strong>[109-11-5]morpholin-3-one</strong> (548.3 mg) as a pale yellow solid.
  • 10
  • [ 20511-12-0 ]
  • [ 3973-08-8 ]
  • [ 1479605-13-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 2h; Step 1:A solution of DIPEA (1.2 mL, 7.0 mmol), A17a (Aldrich, 530 mg, 3.5 mmol) and Ala (300 mg, 2.3 mmol) in DMF (14 mL) is treated with HATU (1.3 g, 3.5 mmol). The mixture is stirred for 2 h and then is diluted with water and EtOAc. The organic layer is separated, washed with water (2 x) and passed through a phase separator. The filtrate is evaporated to dryness and the residue is purified by Combif lash to give A17b.
  • 11
  • [ 20511-12-0 ]
  • [ 20277-69-4 ]
  • [ 35196-11-3 ]
  • 12
  • [ 20511-12-0 ]
  • [ 23152-99-0 ]
  • C15H15N3 [ No CAS ]
  • 13
  • [ 20511-12-0 ]
  • [ 23152-99-0 ]
  • C62H64B2F4N8O2 [ No CAS ]
  • 14
  • [ 20511-12-0 ]
  • [ 2386-57-4 ]
  • [ 35196-11-3 ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In dimethyl sulfoxide; at 100℃;Inert atmosphere; 5-iodopyridin-2-amine (200 mg, 0.91 mmol), sodium methyl sulfinate (186 mg, 1.82 mmol) and potassium carbonate (125 mg, 0.91 mmol) was suspended in dimethyl sulfoxide (10 mL). Copper(I)iodide (35 mg, 0.18 mmol) and N,N,N′,N′- tetramethylethylenediamine (53 mg, 0.46 mmol) was added to the suspension and stirred at 100C under nitrogen overnight. The mixture was cooled, diluted with water and ethyl acetate. The biphasic mixture was passed through a celite bed. The organic layer was separated and washed with water, brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified with silica gel chromatography eluting with ethyl acetate to yield 5-(methylsulfonyl)pyridin-2-amine (130 mg, 83%) as a solid.
 

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Technical Information

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