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Chemical Structure| 17288-52-7 Chemical Structure| 17288-52-7

Structure of 17288-52-7

Chemical Structure| 17288-52-7

*Storage: Inert atmosphere, 2-8°C.

1H-Pyrrolo[3,2-b]pyridine-2-carbaldehyde

CAS No.: 17288-52-7

4.5 *For Research Use Only !

Cat. No.: A701646 Purity: 97%

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Product Details of [ 17288-52-7 ]

CAS No. :17288-52-7
Formula : C8H6N2O
M.W : 146.15
SMILES Code : O=CC1=CC2=NC=CC=C2N1
MDL No. :MFCD08437635
InChI Key :DQSXESUAVDEVJI-UHFFFAOYSA-N
Pubchem ID :22281739

Safety of [ 17288-52-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 17288-52-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 41.48
TPSA ?

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

45.75 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.06
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

0.86
Log Po/w (WLOGP)?

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

1.38
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.

-0.05
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

2.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.08

Water Solubility

Log S (ESOL):?

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

-1.83
Solubility 2.17 mg/ml ; 0.0149 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.

-1.4
Solubility 5.76 mg/ml ; 0.0394 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

-2.84
Solubility 0.213 mg/ml ; 0.00146 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.

-6.58 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<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)

1.37

Application In Synthesis of [ 17288-52-7 ]

* 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 [ 17288-52-7 ]

[ 17288-52-7 ] Synthesis Path-Downstream   1~14

YieldReaction ConditionsOperation in experiment
90% With manganese(IV) oxide; In tetrahydrofuran; at 20℃; for 18.0h; General procedure: [0078] To a solution of (5-(trifluoromethyl)-1H-indol-2-yl)methanol (751 mg,3.49 mmol) in THF (25 mL) was added MnCfi (3034 mg,34.9 mmol) and the mixture was stirred at room temperature for 18 hours. The mixture was then diluted with ethyl acetate and filtered through a pad of celite to afford 5-(trifluoromethyl)-1H-indole-2-carbaldehyde as a yellow solid. [0079] Yield 541 mg (73%, over 2 steps). 1H NMR (400 MHz, DMSO) d 12.40 (s, 1H), 9.95 (s, 1H), 8.23 (s, 1H), 7.66 (d, J=8.9 Hz, 1H), 7.62 (dd, J=1.5, 8.9 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H).
  • 2
  • [ 17288-52-7 ]
  • [ 14384-45-3 ]
  • 2-(4-azaindol-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoline-1-oxyl-3-oxide [ No CAS ]
  • 3
  • [ 569337-21-9 ]
  • [ 17288-52-7 ]
  • 4
  • [ 112671-55-3 ]
  • [ 17288-52-7 ]
  • 5
  • [ 569337-20-8 ]
  • [ 17288-52-7 ]
  • 6
  • 4-Amino-1-[2-(R)-hydroxy-2-(6-methoxyquinolin-4-yl)]ethylpiperidine [ No CAS ]
  • [ 394223-19-9 ]
  • [ 17288-52-7 ]
YieldReaction ConditionsOperation in experiment
(a) 1H-Pyrrolo[3,2-b]pyridin-2-carboxaldehyde This was prepared from methyl 1H-pyrrolo[3,2-b]pyridin-2-carboxylate (0.1 g) and amine (1d) by the method of Example 16c, (except that the alcohol was stirred with manganese (II) oxide overnight) and used without purification.
  • 9
  • 1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde [ No CAS ]
  • [ 17288-52-7 ]
YieldReaction ConditionsOperation in experiment
48.9% With water monomer; sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 20℃; for 1.0h; 1-(Phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde (1.2 g, 4.1 mmol, 1.0 eq) was dissolved in anhydrous THF (15 mL).Cool down to 0 C,A methanol/water mixed solution (1:1 v/v, 30 mL) of sodium hydroxide (1.67 g, 41 mmol, 10 eq) was added dropwise.After the completion of the dropwise addition, the mixture was slowly returned to room temperature for 1 hour.The reaction was completely confirmed by LC-MS and TLC, and the mixture was stirred and evaporated to ethylamine (20mL).The organic phases are combined, washed with saline, dried and concentrated.The crude product was purified by silica gel column chromatography to yield yellow solidThe product was obtained (300 mg, yield: 48.9%).
  • 10
  • [ 17288-52-7 ]
  • (R)-(1-(2-(1-ethyl-1H-pyrrolo[3,2-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-carbonyl)piperidin-3-yl)carbamic acid tert-butyl ester [ No CAS ]
  • 11
  • [ 17288-52-7 ]
  • (R)-(3-aminopiperidin-1-yl)(2-(1-ethyl-1H-pyrrolo[3,2-b]pyridin-2-yl)-7-methoxy-1- methyl-1H-benzo[d]imidazol-5-yl)methanone [ No CAS ]
  • 12
  • [ 17288-52-7 ]
  • [ 75-03-6 ]
  • 1-ethyl-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
42.8% With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 2.0h; 1H-Pyrolo[3,2-b]pyridine-2-carbaldehyde (294 mg, 2 mmol, 1.0 eq) was dissolved in dry DMF (5 mL)Potassium carbonate (552.8 mg, 4 mmol, 2.0 eq) and ethyl iodide (375 mg, 2.4 mmol, 1.2 eq) were added, and the mixture was heated to 40 C for 2 hours. The reaction was completed by LC-MS and TLC, poured into ice water (10 mL), extracted with EA (20 mL×2), washed with brine, dried and concentrated.The product was obtained (150 mg, yield: 42.8%).
  • 13
  • 1-dimethoxyphosphoryl-2-vinylcyclopropane-1-carboxylic acid methyl ester [ No CAS ]
  • [ 17288-52-7 ]
  • methyl 6-vinyl-6,7-dihydropyrido[2,3-b]indolizine-8-carboxylate [ No CAS ]
  • 14
  • [ 17288-52-7 ]
  • [ 78267-15-9 ]
  • ethyl (Z)-5-((1H-pyrrolo[3,2-b]pyridin-2-yl)methylene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With piperidine; In ethanol; for 4.0h;Reflux; General procedure: A mixture of 2a-2n (0.38 mmol), aldehyde 3a-3p and 44 (or ketone 39-43) (0.42 mmol) and piperidine (37.5 µL, 0.38 mmol) in ethanol (3.0 mL) was refluxed for the given time as described individually. The reaction was monitored by TLC. The purification was performed in either of the following two methods. Purification 1. When the product is crystalized as solid during reaction, the reaction mixture was cooled to room temperature slowly. The precipitate is collected by using vacuum filtration with washing cold EtOH. The collected product was dried under low pressured vacuum to give a desired product.
64% With piperidine; In ethanol; for 4.0h;Reflux; General procedure: A mixture of 2a-2n (0.38 mmol), aldehyde 3a-3p and 44 (or ketone 39-43) (0.42 mmol) and piperidine (37.5 µL, 0.38 mmol) in ethanol (3.0 mL) was refluxed for the given time as described individually. The reaction was monitored by TLC. The purification was performed in either of the following two methods. Purification 1. When the product is crystalized as solid during reaction, the reaction mixture was cooled to room temperature slowly. The precipitate is collected by using vacuum filtration with washing cold EtOH. The collected product was dried under low pressured vacuum to give a desired product.
 

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