Home Cart Sign in  
Chemical Structure| 676560-01-3 Chemical Structure| 676560-01-3

Structure of 676560-01-3

Chemical Structure| 676560-01-3

*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 [ 676560-01-3 ]

CAS No. :676560-01-3
Formula : C10H12FNO2
M.W : 197.21
SMILES Code : O=C(OC(C)(C)C)C1=CN=C(F)C=C1
MDL No. :MFCD26743533
InChI Key :RZWMKWGTXCIWLV-UHFFFAOYSA-N
Pubchem ID :66756622

Safety of [ 676560-01-3 ]

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

Computational Chemistry of [ 676560-01-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 49.93
TPSA ?

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

39.19 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.4
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

2.12
Log Po/w (WLOGP)?

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

2.6
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.

1.7
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

2.32
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.23

Water Solubility

Log S (ESOL):?

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

-2.52
Solubility 0.599 mg/ml ; 0.00304 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.

-2.57
Solubility 0.526 mg/ml ; 0.00267 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

-3.21
Solubility 0.122 mg/ml ; 0.000619 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.

-6.0 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)

2.06

Application In Synthesis of [ 676560-01-3 ]

* 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 [ 676560-01-3 ]

[ 676560-01-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 236406-15-8 ]
  • [ 676560-01-3 ]
  • 4-benzyloxycarbonylamino-4-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; hexane; Example 40B 4-Amino-4-methyl-3, 4, 5, 6-tetrahydro-2H-(1,2') bipyridinyl-5'-carboxylic acid tert-butyl ester To a stirred solution of (4-methyl-piperidin-4-yl)-carbamic acid benzyl ester (0.31 g, 1.28 mmol, Example 30B) in dioxane (5.0 mL) at room temperature was added <strong>[676560-01-3]6-fluoro-nicotinic acid tert-butyl ester</strong> (0.21 g, 1.07 mmol). The reaction mixture was stirred at 80 C. for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 10% to 30% ethyl acetate in hexane to provide 4-benzyloxycarbonylamino-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-5'-carboxylic acid tert-butyl ester. MS (CI) m/z 426 (M+1)+; 1H NMR (300 MHz, CDCl3) delta ppm 8.74(d, 1H), 7.97 (dd, 1H), 7.35 (m, 5H), 7.26 (s, 1H), 5.07 (s, 2H), 4.68 (s, 1H), 3.97 (m, 2H), 3.37 (m, 2H), 2.08 (m, 2H), 1.66 (m, 2H), 1.56 (s, 9H), 1.42 (s, 3H).
In 1,4-dioxane; hexane; Example 40B 4-Amino-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-5'-carboxylic acid tert-butyl ester To a stirred solution of (4-methyl-piperidin-4-yl)-carbamic acid benzyl ester (0.31 g, 1.28 mmol, Example 30B) in dioxane (5.0 mL) at room temperature was added <strong>[676560-01-3]6-fluoro-nicotinic acid tert-butyl ester</strong> (0.21 g, 1.07 mmol). The reaction mixture was stirred at 80 C. for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 10% to 30% ethyl acetate in hexane to provide 4-benzyloxycarbonylamino-4methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-5'-carboxylic acid tert-butyl ester. MS (CI) m/z 426 (M+1)+; 1H NMR (300 MHz, CDCl3) delta ppm 8.74(d, 1H), 7.97 (dd, 1H), 7.35 (m, 5H), 7.26 (s, 1H), 5.07 (s, 2H), 4.68 (s, 1H), 3.97 (m, 2H), 3.37 (m, 2H), 2.08 (m, 2H), 1.66 (m, 2H), 1.56 (s, 9H), 1.42 (s, 3H).
In 1,4-dioxane; at 20 - 80℃; for 18.0h; To a stirred solution of (4-methyl-piperidin-4-yl) -carbamic acid benzyl ester (0.31 g, 1.28 mmol, Example 30B) in dioxane (5.0 mL) at room temperature was added 6-fluoro- nicotinic acid tert-butyl ester (0.21 g, 1.07 [MMOL).] The reaction mixture was stirred at 80 [C] for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 10% to 30% ethyl acetate in hexane to provide 4-benzyloxycarbonylamino-4-methyl-3,4, 5,6- [TETRAHYDRO-2H- (1, 2') BIPYRIDINYL-5'-CARBOXYLIC] acid tert-butyl ester. MS (CI) m/z 426 (M+1) [+] ; [JH] NMR (300 MHz, CDC13) 8 ppm 8.74 (d, [1H),] 7.97 (dd, 1H), 7.35 [(M,] [5H),] 7.26 (s, [1H),] 5.07 (s, 2H), 4.68 (s, [1H),] 3.97 (m, 2H), 3.37 [(M,] 2H), 2.08 [(M,] 2H), 1.66 (m, 2H), 1.56 (s, 9H), 1.42 (s, 3H). To a stirred solution [OF 4-BENZYLOXYCARBONYLAMINO-4-METHYL-3, 4, 5, 6-TETRAHYDRO-2H-] (1, 2') [BIPYRIDINYL-5'-CARBOXYLIC] acid tert-butyl ester (0.29 g, 0.68 mmol) in isopropanol, methanol and ethyl acetate (1: 1: 1,5. 0 mL) at room temperature was added ammonium formate (0.25 g, 1.07 mmol) and 10% Pd/C (25 mg) under nitrogen. The reaction mixture was stirred at 80 [C] for 30 minutes, cooled, filtered through Celite, and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 292 (M+1) [+] [;'H] NMR (300 MHz, methanol-d4) [8] ppm 8.61 (d, [1H),] 7.95 (d, d [1H),] 6.79 (d, [1H),] 4.80 (s, 2H), 3.85-3. 79 [(M,] 2H), 3.66-3. 60 [(M,] 2H), 1.67-1. 59 (m, 4H), 1.58 (s, 9H), 1.23 (s, 3H).
  • 2
  • [ 403-45-2 ]
  • [ 36805-97-7 ]
  • [ 676560-01-3 ]
  • 3
  • [ 403-45-2 ]
  • [ 75-65-0 ]
  • [ 676560-01-3 ]
YieldReaction ConditionsOperation in experiment
With N,N-dimethylformamide di-tert-butyl acetal; for 3.0h;Heating / reflux; To a stirred and refluxed solution of 6-fluoro-nicotinic acid (0.092 g, 6.52 mmol) in benzene and 2-methyl-propan-2-ol (2: 1,15 : 7 mL) was added dropwise N, N- [DIMETHYLFORMAMIDE] di-tert-butyl acetal (8.2 mL, 29.6 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature and partitioned between aqueous [NAHC03] and dichloromethane. The organic layer was washed with water and brine, dried [(MGS04),] filtered, concentrated under reduced pressure and purified by flash chromatography with 15% to 30% ethyl acetate in hexane to provide the titled compound. MS (CI) m/z 197 (M+1) [+] [; IH] NMR (300 MHz, CDC13) [5] ppm 8.82 (d, 1H), 8.38 (m, 1H), 6.98 (d, [1H),] 1.64 (s, 9H).
  • 4
  • [ 403-45-2 ]
  • [ 75-65-0 ]
  • [ 36805-97-7 ]
  • [ 676560-01-3 ]
YieldReaction ConditionsOperation in experiment
In hexane; benzene; Example 40A 6-Fluoro-nicotinic acid tert-butyl ester To a stirred and refluxed solution of 6-fluoro-nicotinic acid (0.092 g, 6.52 mmol) in benzene and 2-methyl-propan-2-ol (2:1, 15:7 mL) was added dropwise N,N-dimethylformamide di-tert-butyl acetal (8.2 mL, 29.6 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature and partitioned between aqueous NaHCO3 and dichloromethane. The organic layer was washed with water and brine, dried (MgSO4), filtered, concentrated under reduced pressure and purified by flash chromatography with 15% to 30% ethyl acetate in hexane to provide the titled compound. MS (CI) m/z 197 (M+1)+; 1H NMR (300 MHz, CDCl3) delta ppm 8.82(d, 1H), 8.38(m, 1H), 6.98(d, 1H), 1.64 (s, 9H).
  • 5
  • [ 676560-01-3 ]
  • [ 813433-93-1 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; Example 190A 6-(4-amino-4-methyl-cyclohexyloxy)-N,N-dimethyl-nicotinamide To a mixture of sodium hydride (240 mg, 6.0 mmol) in dimethylformamide (10 mL) at 0 C. was added Example 45F (258 mg, 2.0 mmol). The resulting mixture was stirred at 0 C. for 30 minutes, then Example 40A (473 mg, 2.4 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 278 (M+H)+.
In N-methyl-acetamide; Example 190A 6-(4-amino-4-methyl-cyclohexyloxy)-N,N-dimethyl-nicotinamide To a mixture of sodium hydride (240 mg, 6.0 mmol) in dimethylformamide (10 mL) at. 0 C. was added Example 45F (258 mg, 2.0 mmol). The resulting mixture was stirred at 0 C. for 30 minutes, then Example 40A (473 mg, 2.4 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 278 (M+H)+.
  • 6
  • [ 65321-36-0 ]
  • [ 676560-01-3 ]
  • tert-butyl 2-fluoronicotinate [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 676560-01-3 ]

Fluorinated Building Blocks

Chemical Structure| 944582-95-0

A122663 [944582-95-0]

6-Fluoro-4-methylnicotinic acid

Similarity: 0.81

Chemical Structure| 1227595-02-9

A124393 [1227595-02-9]

Methyl 6-fluoro-2-methylnicotinate

Similarity: 0.81

Chemical Structure| 402-65-3

A167062 [402-65-3]

2-Fluoroisonicotinic acid

Similarity: 0.77

Chemical Structure| 405939-62-0

A254798 [405939-62-0]

Methyl 5-bromo-6-fluoronicotinate

Similarity: 0.76

Chemical Structure| 884494-97-7

A192524 [884494-97-7]

6-Fluoro-2-methylnicotinic acid

Similarity: 0.76

Esters

Chemical Structure| 1227595-02-9

A124393 [1227595-02-9]

Methyl 6-fluoro-2-methylnicotinate

Similarity: 0.81

Chemical Structure| 614-18-6

A107966 [614-18-6]

Ethyl nicotinate

Similarity: 0.80

Chemical Structure| 94-44-0

A100203 [94-44-0]

Benzyl nicotinate

Similarity: 0.78

Chemical Structure| 20826-02-2

A226731 [20826-02-2]

Ethyl 5-methylnicotinate

Similarity: 0.78

Chemical Structure| 273203-62-6

A328129 [273203-62-6]

Tetradecyl pyridine-3-carboxylate

Similarity: 0.78

Related Parent Nucleus of
[ 676560-01-3 ]

Pyridines

Chemical Structure| 944582-95-0

A122663 [944582-95-0]

6-Fluoro-4-methylnicotinic acid

Similarity: 0.81

Chemical Structure| 1227595-02-9

A124393 [1227595-02-9]

Methyl 6-fluoro-2-methylnicotinate

Similarity: 0.81

Chemical Structure| 614-18-6

A107966 [614-18-6]

Ethyl nicotinate

Similarity: 0.80

Chemical Structure| 20826-02-2

A226731 [20826-02-2]

Ethyl 5-methylnicotinate

Similarity: 0.78

Chemical Structure| 273203-62-6

A328129 [273203-62-6]

Tetradecyl pyridine-3-carboxylate

Similarity: 0.78