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Chemical Structure| 10167-97-2 Chemical Structure| 10167-97-2

Structure of 10167-97-2

Chemical Structure| 10167-97-2

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Product Details of [ 10167-97-2 ]

CAS No. :10167-97-2
Formula : C6H8N2O
M.W : 124.14
SMILES Code : NC1=NC=C(C=C1)OC
MDL No. :MFCD07374873
InChI Key :XJKJHILCYUUVSJ-UHFFFAOYSA-N
Pubchem ID :11320934

Safety of [ 10167-97-2 ]

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

Computational Chemistry of [ 10167-97-2 ] 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 2.0
Num. H-bond donors 1.0
Molar Refractivity 35.13
TPSA ?

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

48.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.64
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

0.48
Log Po/w (WLOGP)?

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

0.68
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.

-0.07
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

0.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.67

Water Solubility

Log S (ESOL):?

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

-1.34
Solubility 5.68 mg/ml ; 0.0458 mol/l
Class?

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

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.06
Solubility 10.8 mg/ml ; 0.087 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

-1.75
Solubility 2.21 mg/ml ; 0.0178 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.

-6.72 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)

1.68

Application In Synthesis of [ 10167-97-2 ]

* 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 [ 10167-97-2 ]

[ 10167-97-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 63920-75-2 ]
  • [ 10167-97-2 ]
  • 2-amino-4,6-dimethoxy-<i>N</i>-(5-methoxy-pyridin-2-yl)-benzamide [ No CAS ]
  • 2
  • [ 62266-36-8 ]
  • [ 10167-97-2 ]
  • 2-methylene-cyclopropanecarboxylic acid (5-methoxy-pyridin-2-yl)-amide [ No CAS ]
  • 3
  • [ 10167-97-2 ]
  • [ 55717-46-9 ]
YieldReaction ConditionsOperation in experiment
51.8% With sulfuric acid; at 90 - 93℃; for 24h; 95 percent H2SO4 (10 mL) was stirred at 80 °C, compound 5 (5 mmol, 0.62 g) was added dropwise to the stirred solution keeping the temperature at 80-85 °C. After the addition, stirring was continued at 90-93 °C for about 24 h until 5 can not be detected by TLC. The reaction mixture was poured into crash ice (100 g) and the solution was adjusted to pH 7-8 by gradual addition of Na2CO3. The resulting mixture was extracted several times with diethyl ether (Scheme-I). The combined organic phases were dried with anhydrous Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (gradient elution: CH3OH/CH2Cl2 = 1:9) to give taupe solid 6 (0.29 g, yield = 51.8 percent). 1H NMR (400 Hz, DMSO-d6), delta (ppm): 5.200 (br, 2H, NH2), 6.327-6.350 (t, 1H, pyr-H), 6.893-6.923 (dd, 1H, pyr-H), 7.497-7.506 (dd, 1H, pyr-H), 8.636 (s, 1H, OH). 13C NMR (100 MHz, DMSO-d6), delta (ppm): 110.00, 128.16, 131.65, 145.25, 150.04.
44% A solution of compound 119 in a 48percent aqueous HBr solution was refluxed overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography (dichloromethane / methanol (7M NH3) 9:1) to give 6-amino-pyridin-3-ol (120) (6.9 g, yield = 44percent) as dark brown crystals. 1H NMR (delta, DMSO-D6): 5.19 (2H, s), 6.33 (IH, d, J = 8.7 Hz), 6.90 (IH, dd, J = 8.7, 3.0 Hz), 7.50 (IH, d, J = 3.0 Hz), 8.61 (IH, s).
  • 4
  • [ 37904-72-6 ]
  • [ 10167-97-2 ]
  • 4-(6-methoxy-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% 4-(6-methoxy-H-imidazo[l,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine (L9).; In a 2-necked round bottomed flask equipped with a condenser and under nitrogen flow were introduced the <strong>[10167-97-2]2-amino-5-methoxypyridine</strong> (0.15 g, 1.17 mmol), the 2-bromo-4'- dimethylamino-acetophenone (0.31 g, 1.29 mmol) and 14 mL of absolute EtOH. The reaction mixture was stirred at reflux for 2 h. After it cooled down, NaHCO3 (0.15 g, 1.75 mmol) was added, the mixture was refluxed for another 6 hrs. After the solvent was removed, the residue was dissolved in AcOEt. The organic phase was washed with water, dried over MgSO4, and filtered. The solvent was removed to afford 0.271 g crude product, which was purified by FCC (DCM/ AcOEt = 1:1) to give 0.129 g (yield 41percent) of the product as yellow solid. M.p. = <n="16"/>177-179°C. 1H NMR (270 MHz; CDCl3), delta 7.82 (d, 3JHH = 8.7 Hz, 2H, Ar-H), 7.71 (s, IH, H-3), 7.65 (s, IH, Ar-H), 7.53 (d, 3JHH = 9.6 Hz, IH, Ar-H), 6.96 (dd, 3JHH = 9.6, 4JHH = 1.8, IH, Ar-H), 6.81 (d, 3JHH = 8.8, 2H, Ar-H), 3.84 (s, 3H, OCH3), 3.02 (s, 6H, NCH3); 13C(1H) NMR (125 MHz, CDCl3), delta 151.0, 150.4, 149.2, 146.0, 143.0, 126.8 (Ph-2,6), 119.2 (C7), 117.0 (C8), 112.5 (Ph-3,5), 107.6 (C3), 106.2 (C5), 56.2 (OCH3), 40.5 (NCH3). m/z (EI-MS): 267 (At), 252 (M+-CH3); CaIc. C16HnN3O: C, 71.89; H, 6.41; N, 15.72. Found: C, 71.60; H, 6.62; N, 15.96.
  • 5
  • [ 10167-97-2 ]
  • 5-methoxy-5'-methyl-2,2'-bipyridine [ No CAS ]
  • 6
  • [ 477889-91-1 ]
  • [ 10167-97-2 ]
  • 7
  • [ 10167-97-2 ]
  • [ 431942-24-4 ]
  • 8
  • [ 10167-97-2 ]
  • [ 431942-28-8 ]
  • 9
  • [ 10167-97-2 ]
  • [ 431942-33-5 ]
  • 10
  • [ 10167-97-2 ]
  • [ 431942-32-4 ]
  • 11
  • [ 10167-97-2 ]
  • 3-bromomethyl-5-methoxy-2-phenyl-furo[2,3-<i>b</i>]pyridine [ No CAS ]
  • 12
  • [ 10167-97-2 ]
  • [ 431942-34-6 ]
  • 13
  • [ 10167-97-2 ]
  • N-[2-(5-methoxy-2-phenylfuro[2,3-b]pyridin-3-yl)ethyl]acetamide [ No CAS ]
  • 15
  • [ 10167-97-2 ]
  • [ 22187-96-8 ]
  • 16
  • [ 10167-97-2 ]
  • [ 325796-80-3 ]
  • 17
  • [ 10167-97-2 ]
  • [ 325796-82-5 ]
  • 18
  • [ 10167-97-2 ]
  • 5-Methoxy-2-(1-methoxycarbonyl-2,3-dihydro-1H-indol-3-ylmethyl)-1-methylpyridiniumiodid [ No CAS ]
  • 19
  • [ 10167-97-2 ]
  • [ 325796-84-7 ]
  • 20
  • [ 10167-97-2 ]
  • [ 325796-81-4 ]
  • 21
  • [ 10167-97-2 ]
  • 3-(5-Methoxypyridin-2-ylmethyl)-1H-indol [ No CAS ]
  • 22
  • [ 10167-97-2 ]
  • [ 325796-74-5 ]
  • 23
  • [ 10167-97-2 ]
  • [ 325796-73-4 ]
  • 24
  • [ 10167-97-2 ]
  • [ 325796-77-8 ]
  • 25
  • [ 10167-97-2 ]
  • 3-[1-Hydroxy-1-(5-methoxypyridin-2-yl)-methyl]-indol-1-carbonsaeuremethylester [ No CAS ]
  • 26
  • [ 10167-97-2 ]
  • [ 325796-76-7 ]
  • 27
  • [ 10167-97-2 ]
  • [ 325796-79-0 ]
  • 28
  • [ 10167-97-2 ]
  • [ 325796-72-3 ]
  • 29
  • [ 10167-97-2 ]
  • C23H24BN3O [ No CAS ]
  • 30
  • [ 10167-97-2 ]
  • Bis-(1-benzylindol-3-yl)-5-methoxypyridin-2-yl-methan [ No CAS ]
  • 31
  • [ 10167-97-2 ]
  • [ 196959-51-0 ]
  • 32
  • [ 10167-97-2 ]
  • Acetoxy-[2-(4-chloro-phenyl)-6-methoxy-imidazo[1,2-a]pyridin-3-yl]-acetic acid ethyl ester [ No CAS ]
  • 33
  • [ 10167-97-2 ]
  • Acetylamino-[2-(4-chloro-phenyl)-6-methoxy-imidazo[1,2-a]pyridin-3-yl]-acetic acid ethyl ester [ No CAS ]
  • 34
  • [ 10167-97-2 ]
  • Benzoylamino-[2-(4-chloro-phenyl)-6-methoxy-imidazo[1,2-a]pyridin-3-yl]-acetic acid ethyl ester [ No CAS ]
  • 35
  • [ 10167-97-2 ]
  • [ 117296-85-2 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 10167-97-2 ]

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Related Parent Nucleus of
[ 10167-97-2 ]

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