Home Cart Sign in  
Chemical Structure| 478148-61-7 Chemical Structure| 478148-61-7

Structure of 478148-61-7

Chemical Structure| 478148-61-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 478148-61-7 ]

CAS No. :478148-61-7
Formula : C8H5NO2
M.W : 147.13
SMILES Code : O=CC1=CC2=C(OC=C2)C=N1
MDL No. :MFCD11109706
InChI Key :LKXRQBNEOKIHRW-UHFFFAOYSA-N
Pubchem ID :22047533

Safety of [ 478148-61-7 ]

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

Computational Chemistry of [ 478148-61-7 ] 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 3.0
Num. H-bond donors 0.0
Molar Refractivity 39.4
TPSA ?

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

43.1 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.1
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

1.05
Log Po/w (WLOGP)?

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

1.64
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.

-0.32
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

2.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.1

Water Solubility

Log S (ESOL):?

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

-1.95
Solubility 1.64 mg/ml ; 0.0111 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.

-1.55
Solubility 4.19 mg/ml ; 0.0285 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 0.212 mg/ml ; 0.00144 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.

-6.45 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)

2.01

Application In Synthesis of [ 478148-61-7 ]

* 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 [ 478148-61-7 ]

[ 478148-61-7 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 478148-61-7 ]
  • [ 478148-62-8 ]
YieldReaction ConditionsOperation in experiment
94% With potassium dihydrogenphosphate; NaClO2; In methanol; water; dimethyl sulfoxide; C17 (850 mg, 5.8 mmol) is dissolved in 10 mL DMSO. KH2PO4 (221 mg, 1.6 mmol) in 3 mL H2O is added and then NaClO2 (920 mg, 8.2 mmol) in 7 mL H2O is added, and the reaction is stirred 3 h at rt. The reaction is diluted with 25 mL water, the pH is adjusted to 10 with 2N NaOH, and the mixture is extracted with 3*20 mL ether. The combined ether layer is discarded. The pH of the aqueous layer is adjusted to 3.5 with 10% aqueous HCl and is extracted with 13*10 mL 10% MeOH/CH2Cl2. The MeOH/CH2Cl2 organic layer is dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to a pale oil. The residual DMSO is removed under a stream of N2 at rt to provide a white paste. The paste is dissolved in MeOH and concentrated to dryness. The white solid is washed with ether and dried to afford crude furo[2,3-c]pyridine-5-carboxylic acid (C18) (94% yield). MS (ESI) for C8H5NO3, 162.8 (M-H)-.
94% With potassium dihydrogenphosphate; NaClO2; In methanol; water; dimethyl sulfoxide; C17 (850 mg, 5.8 mmol) is dissolved in 10 mL DMSO. KH2PO4 (221 mg, 1.6 mmol) in 3 mL water is added and then NaClO2 (920 mg, 8.2 mmol) in 7 mL water is added, and the reaction is stirred 3 h at rt. The reaction is diluted with 25 mL water, the pH is adjusted to 10 with 2N NaOH, and the mixture is extracted with 3*20 mL ether. The combined ether layer is discarded. The pH of the aqueous layer is adjusted to 3.5 with 10% aqueous HCl and is extracted with 13*10 mL 10% MeOH/CH2Cl2. The MeOH/CH2Cl2 organic layer is dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to a pale oil. The residual DMSO is removed under a stream of N2 at rt to provide a white paste. The paste is dissolved in MeOH and is concentrated to dryness. The white solid is washed with ether and dried to afford crude furo[2,3-c]pyridine-5-carboxylic acid (C18) (94% yield). MS (ESI) for C8H5NO3, 162.8 (M-H)-.
94% With sodium chlorite; potassium dihydrogenphosphate; In water; dimethyl sulfoxide; at 20℃; for 3h; C8 (850 mg, 5.8 mmol) is dissolved in 10 mL DMSO. KH2PO4 (221 mg, 1.6 mmol) in 3 mL water is added and then NA102 (920 mg, 8.2 mmol) in 7 mL water is added, and the reaction is stirred 3h at rt. The reaction is diluted with 25 mL water, the pH is adjusted to 10 with 2N NAOH, AND the mixture is extracted with 3 x 20 mL ether. The combined ether layer is discarded. The pH of the aqueous layer is adjusted to 3.5 with 10% aqueous HC1 and is extracted with 13 X 10 mL 10% MEOH/CH2CL2. The MEOH/CH2CL2 organic layer is dried (NA2S04), filtered, and concentrated in vacuo to a pale oil. The residual DMSO is removed under a stream of N2 at rt to provide a white paste. The paste is dissolved in MEOH and is concentrated to dryness. The white solid is washed with ether and dried to afford crude furo [2,3-c] pyridine-5- carboxylic acid C9) (94% YIELD). MS (ESI) FOR CSHSNO3 162.8 (M-H)-.
  • 2
  • [ 478148-60-6 ]
  • [ 478148-61-7 ]
YieldReaction ConditionsOperation in experiment
95% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; In acetone; at 20℃; for 0.0833333h;Cooling with ice; a-9) Preparation of furo[2,3-c]pyridine-5-carbaldehyde Furo[2,3-c]pyridin-5-yl methanol (521 mg, 3.49 mmol) was dissolved in acetone (17 mL), added 2,2,6,6-tetramethylpiperidine 1-oxyl (27 mg, 170 mumol) at room temperature. Then, the reaction solution was added 1,3,5-trichloro-2,4,6-triazinetrione (892 mg, 3.84 mmol) under ice-cold conditions, and stirred at the same temperature for 5 minutes. The reaction solution was concentrated in vacuo, added water and a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (488 mg (yield 95%)) was obtained as a yellow solid. 1H-NMR (CDCl3) delta: 6.98 (1H, dd, J=0.8, 2.2 Hz), 7.88 (1H, d, J=2.2 Hz), 8.32 (1H, d, J=0.8 Hz), 9.03 (1H, s), 10.18 (1H, s).
86% Oxalyl chloride (685AL, 7.8 mmol) is dissolved in 30 mL CH2C12 in a dry flask under N2. The flask is placed in a DRY-ICE/ACETONE bath, DMSO (1. 11 mL, 15. 6 mmol) in 5 mL CH2C12 is added drop-wise, and the mixture is stirred for 20 min. C7 (1.0 g, 6.7 mmol) in 10 mL CH2C12 is added, and the reaction is stirred 30 min at - 78C. TEA (4.7 mL, 33.5 mmol) is added, the reaction is allowed to warm to rt, is stirred 1 h, and is washed with 25 mL saturated NAHC03. The organic layer is dried (K2CO3), filtered, and concentrated in vacuo to an orange solid. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluting with 33% EtOAc/ hexane. The fractions with the desired compound are combined and concentrated to provide furo [2,3-c] PYRIDINE-5-CARBALDEHYDE (C8 AS A WHITE SOLID (86% YIELD). MS (EI) for C8HSNO2, NILZ : 147 (M) +.
YieldReaction ConditionsOperation in experiment
86% Oxalyl chloride (685 muL, 7.8 mmol) is dissolved in 30 mL CH2Cl2 in a dry flask under N2. The flask is placed in a dry-ice/acetone bath, DMSO (1.11 mL, 15.6 mmol) in 5 mL CH2Cl2 is added drop-wise, and the mixture is stirred for 20 min. C 16 (1.0 g, 6.7 mmol) in 10 mL CH2Cl2 is added, and the reaction is stirred 30 min at -78 C. TEA (4.7 mL, 33.5 mmol) is added, the reaction is allowed to warm to rt, is stirred 1 h, and washed with 25 mL saturated NaHCO3. The organic layer is dried over anhydrous K2CO3, filtered, and concentrated in vacuo to an orange solid. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluding with 33% EtOAc/hexane to provide furo[2,3-c]pyridine-5-carbaldehyde (C17) as a white solid (86% yield). MS (EI) for C8H5NO2, m/z: 147 (M)+.
  • 10
  • [ 478148-60-6 ]
  • [ 79-37-8 ]
  • [ 478148-61-7 ]
YieldReaction ConditionsOperation in experiment
86% With triethanolamine; In dichloromethane; dimethyl sulfoxide; Oxalyl chloride (685 muL, 7.8 mmol) is dissolved in 30 mL CH2Cl2 in a dry flask under N2. The flask is placed in a dry-ice/acetone bath, DMSO (1.11 mL, 15.6 mmol) in 5 mL CH2Cl2 is added drop-wise, and the mixture is stirred for 20 min. C16 (1.0 g, 6.7 mmol) in 10 mL CH2Cl2 is added, and the reaction is stirred 30 min at -78 C. TEA (4.7 mL, 33.5 mmol) is added, the reaction is allowed to warm to rt, is stirred 1 h, and is washed with 25 mL saturated NaHCO3. The organic layer is dried over anhydrous K2CO3, filtered, and is concentrated in vacuo to an orange solid. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluding with 33% EtOAc/hexane. The fractions with the desired compound are combined and concentrated to provide furo[2,3-c]pyridine-5-carbaldehyde (C17) as a white solid (86% yield). MS (EI) for C8H5NO2, m/z: 147 (M)+.
850 mg (86%) With triethylamine; In dichloromethane; dimethyl sulfoxide; Oxalyl chloride (685 muL, 7.8 mmol) is dissolved in 30 ml CH2Cl2 in a dried flask under nitrogen. The solution is cooled in a dry ice/acetone bath, is treated drop-wise with DMSO (1.11 ml, 15.6 mmol) in 1*5 ml CH2Cl2, and the mixture is stirred for 20 min. The mixture is treated with furo[2,3-c]pyridin-5-yl methanol (1.0 g, 6.7 mmol) in 1*10 ml CH2Cl2, is stirred 30 min at in a dry ice/acetone bath, and is treated with Et3N (4.7 ml, 33.5 mmol). The reaction is allowed to warm to rt, is stirred 1 h, and is washed with 1*25 ml saturated NaHCO3. The organic layer is dried over K2CO3 and is concentrated in vacuo to an orange solid. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluding with 33% EtOAc/hexane. The appropriate fractions are combined and concentrated to provide 850 mg (86%) of furo[2,3-c]pyridine-5-carbaldehyde as a white solid. MS for C8H5NO2, (EI) m/z: 147 (M)+.
  • 11
  • [ 478148-61-7 ]
  • [ 7758-19-2 ]
  • potassium dihydrogen phosphate [ No CAS ]
  • [ 478148-62-8 ]
YieldReaction ConditionsOperation in experiment
890 mg (94%) In methanol; water; dimethyl sulfoxide; Furo[2,3-c]pyridine-5-carbaldehyde (850 mg, 5.8 mmol) is dissolved in 10 ml DMSO. To this solution is added potassium dihydrogen phosphate (221 mg, 1.6 mmol) in 3 ml water followed by sodium chlorite (920 mg, 8.2 mmol) in 7 ml water. The resulting reaction mixture is stirred for 3 h at rt. The reaction is diluted with 25 ml water, the pH is adjusted to 10 with 2N NaOH, and the mixture is extracted with 3*20 ml ether. The pH of the aqueous layer is adjusted to 3.5 with 10% aqueous HCl and is extracted with 13*10 ml 10% MeOH/CH2Cl2. The organic layer is dried over Na2SO4 and is concentrated in vacuo to a pale oil. The residual DMSO is removed under a stream of nitrogen to provide a white paste. The paste is dissolved in MeOH and is concentrated to dryness. The white solid is washed with ether and is dried to give 890 mg (94%) of crude furo[2,3-c]pyridine-5-carboxylic acid. MS for C8H5NO3, (ESI): 162.8 (M-H)-.
  • 12
  • [ 478148-61-7 ]
  • [ 75-16-1 ]
  • [ 185220-77-3 ]
YieldReaction ConditionsOperation in experiment
66% In tetrahydrofuran; at 20℃; for 1.5h;Cooling with ice; a-10) Preparation of 1-(furo[2,3-c]pyridin-5-yl)ethanol Under an argon atmosphere, <strong>[478148-61-7]furo[2,3-c]pyridine-5-carbaldehyde</strong> (488 mg, 3.31 mmol) was dissolved in tetrahydrofuran (11 mL), and added methylmagnesium bromide (5.5 mL (1.0 M in THF solution), 4.97 mmol) under ice-cold conditions. Then, the mixture was stirred at room temperature for 1.5 hours. The reaction solution was added 1N-aqueous solution of hydrochloric acid under ice-cold conditions, and then a saturated aqueous solution of sodium hydrogen carbonate was added. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (356 mg (yield 66%)) was obtained as a yellow solid. 1H-NMR (CDCl3) delta: 1.56 (3H, d, J=6.2 Hz), 5.00 (1H, q, J=6.2 Hz), 6.80 (1H, d, J=2.2 Hz), 7.53 (1H, s), 7.78 (1H, d, J=2.2 Hz), 8.80 (1H, s).
  • 13
  • [ 478148-61-7 ]
  • N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide, hemi-fumarate salt [ No CAS ]
  • 14
  • [ 478148-61-7 ]
  • [ 708261-37-4 ]
  • 15
  • [ 478148-59-3 ]
  • [ 478148-61-7 ]
  • 16
  • [ 441044-90-2 ]
  • [ 478148-61-7 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 478148-61-7 ]

Aldehydes

Chemical Structure| 527681-61-4

A229772 [527681-61-4]

3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

Similarity: 0.87

Chemical Structure| 1849-52-1

A284636 [1849-52-1]

3-Methoxyisonicotinaldehyde

Similarity: 0.74

Chemical Structure| 443955-90-6

A118134 [443955-90-6]

2,3-Dihydro-[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde

Similarity: 0.69

Chemical Structure| 4363-94-4

A154472 [4363-94-4]

6-Methoxyquinoline-4-carbaldehyde

Similarity: 0.69

Chemical Structure| 1060804-48-9

A964627 [1060804-48-9]

5-Hydroxynicotinaldehyde

Similarity: 0.65

Related Parent Nucleus of
[ 478148-61-7 ]

Other Aromatic Heterocycles

Chemical Structure| 478148-62-8

A297042 [478148-62-8]

Furo[2,3-c]pyridine-5-carboxylic acid

Similarity: 0.87

Chemical Structure| 527681-61-4

A229772 [527681-61-4]

3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

Similarity: 0.87

Chemical Structure| 478148-60-6

A126154 [478148-60-6]

Furo[2,3-c]pyridin-5-ylmethanol

Similarity: 0.85

Chemical Structure| 19539-50-5

A279212 [19539-50-5]

Furo[2,3-c]pyridine

Similarity: 0.80

Chemical Structure| 112372-15-3

A202100 [112372-15-3]

Furo[2,3-c]pyridine-2-carboxylic acid

Similarity: 0.77