Home Cart Sign in  
Chemical Structure| 149554-03-0 Chemical Structure| 149554-03-0

Structure of 149554-03-0

Chemical Structure| 149554-03-0

*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 [ 149554-03-0 ]

CAS No. :149554-03-0
Formula : C11H19NO3
M.W : 213.27
SMILES Code : O=C(OC(C)(C)C)CN1CCC(CC1)=O
MDL No. :MFCD07371646
InChI Key :SBVOSDPEDKERMR-UHFFFAOYSA-N
Pubchem ID :53407149

Safety of [ 149554-03-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 149554-03-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 61.21
TPSA ?

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

46.61 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.5
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

0.62
Log Po/w (WLOGP)?

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

0.61
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.

0.64
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

1.52
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.18

Water Solubility

Log S (ESOL):?

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

-1.29
Solubility 11.0 mg/ml ; 0.0514 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.

-1.17
Solubility 14.3 mg/ml ; 0.0671 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

-1.8
Solubility 3.34 mg/ml ; 0.0157 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.

-7.16 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

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)

1.76

Application In Synthesis of [ 149554-03-0 ]

* 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 [ 149554-03-0 ]

[ 149554-03-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 107-59-5 ]
  • [ 40064-34-4 ]
  • [ 149554-03-0 ]
  • 2
  • [ 149554-03-0 ]
  • [ 68104-63-2 ]
  • [ 149554-04-1 ]
  • 3
  • [ 149554-03-0 ]
  • GR144053 [ No CAS ]
  • 4
  • [ 149554-03-0 ]
  • [ 149554-31-4 ]
  • 5
  • [ 32566-01-1 ]
  • [ 149554-03-0 ]
  • C24H27N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; for 192.0h;Heating / reflux; A mixture of 45 (2.1 g, 10 mmol), BOC-piperidone (3.4 g, 17 [MMOL)] and KOH (0.28 g, 5 [MMOL)] in CH30H (150 ml) was [REFLUXED] for eight days. The reaction mixture was then concentrated in vacuo, partitioned between water (50 [ML)] and [CH2CI2] (100 [ML),] and acidified with [ACOH.] The organic layer was isolated and concentrated to provide crude 46.
  • 6
  • [ 149554-03-0 ]
  • [ 181943-04-4 ]
YieldReaction ConditionsOperation in experiment
Referential Example 2 Methyl 1-(tert-butoxycarbonylmethyl)-4-oxo-3-piperidinepropionate Starting compound: <strong>[149554-03-0]Tert-butyl 4-oxo-1-piperidineacetate</strong> Mass spectrum (m/z): FAB (Pos) 300(M+ +1) NMR spectrum (CDCl3, TMS internal standard): delta: 1.48 (9H, s), 1.50-1.59 (1H, m), 2.05-2.15 (1H, m), 2.30-2.46 (4H, m), 2.60-2.70 (3H, m), 3.13-3.17 (2H, m), 3.25 (2H, d), 3.66 (3H, s).
  • 7
  • 4-(5-fluoro-2-methoxyphenyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride [ No CAS ]
  • [ 149554-03-0 ]
  • tert-butyl 2-(4-(4-(4-(5-fluoro-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)piperidin-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; triethylamine; In methanol; dichloromethane; at 40℃; for 3.0h; To a mixture of Example 87D (0.200 g, 0.505 mmol) and triethylamine (0.155 mL, 1.1 10 mmol), acetic acid (0.144 mL, 2.52 mmol) in dichloromethane (3 mL) and methanol (3 mL) was added tert-butyl 2-(4-oxopiperidin- 1 -yl)acetate (0.215 g, 1.009 mmol) and MP-cyanoborohydride (Biotage, 81 1 mg, 2.019 mmol). The reaction mixture was heated at 40C for 3 hours. The solid material was filtered and rinsed with dichloromethane and methanol. The filtrate was concentrated. The residue was partitioned in ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated until most solvent was evaporated. The precipitates were filtered, washed with cold ethyl acetate, and vacuum oven-dried to provide the title compound. MS (ESI+) m/z 521.1 (M+H)+.
  • 8
  • [ 99-09-2 ]
  • [ 149554-03-0 ]
  • C17H25N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.5% Example A13e a) Preparation of Int. 229 3-Nitro-aniline (5.0 g; 36.2 mmol) was dissolved in DCE (75 ml). Tert-butyl 4- oxopiperidine-1 -acetate (15.4 g; 72.4 mmol) and acetic acid (4.3 g; 72.4 mmol) were added. The mixture was stirred at r.t. for 1 h, then sodiumacetoxyboro hydride (15.3 g; 72.4 mmol) was added in portions. The mixture was stirred at r.t. overnight. The mixture was washed with water, brine, dried, and concentrated to give 3.0 g of Int. 229 (69.5 %).
  • 9
  • tert-butyl 3-(1-((3-(2-aminoethoxy)-5,7-dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)-6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)picolinate [ No CAS ]
  • [ 149554-03-0 ]
  • 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl]-3-(1-[3-(2-[1-(carboxymethyl)piperidin-4-yl]amino}ethoxy)-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl]methyl}-5-methyl-1H-pyrazol-4-yl)pyridine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
[000627] A solution of Example 1.2.7 (0.055 g,), fert-butyl 2-(4-oxopiperidin-l-yl)acetate (0.014 g) and sodium triacetoxyborohydride (0.019 g) was stirred in dichloromethane (0.5 mL) at room temperature. After stirring for 2 hours, trifluoroacetic acid (0.5 mL) was added to the reaction, and stirring was continued overnight. The reaction was concentrated, dissolved in N,N- dimethylformamide (1.5 mL) and water (0.5 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 10-80% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. NMR (501 MHz, dimethyl sulfoxide-^) delta ppm 12.85 (s, 1H), 8.80 (s, 2H), 8.03 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.55-7.41 (m, 3H), 7.36 (q, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.07 (s, 2H), 3.89 (t, 2H), 3.83 (s, 2H), 3.66-3.55 (m, 4H), 3.30 (s, 1H), 3.08 (s, 4H), 3.02 (t, 2H), 2.22 (d, 2H), 2.10 (s, 3H), 1.97-1.78 (m, 2H), 1.44 (s, 2H), 1.31 (q, 4H), 1.20-0.96 (m, 6H), 0.87 (s, 6H). MS (ESI) m/e 887.3 (M+H)+.
A solution of Example 1.2.7 (0.055 g,), <strong>[149554-03-0]tert-butyl 2-(4-oxopiperidin-1-yl)acetate</strong> (0.014 g) and sodium triacetoxyborohydride (0.019 g) was stirred in dichloromethane (0.5 mL) at room temperature. After stirring for 2 hours, trifluoroacetic acid (0.5 mL) was added to the reaction, and stirring was continued overnight. The reaction was concentrated, dissolved in N,N- dimethylformamide (1.5 mL) and water (0.5 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 10-80% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. 1H NMR (501 MHz, dimethyl sulfoxide-d6) delta ppm 12.85 (s, 1H), 8.80 (s, 2H), 8.03 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.55-7.41 (m, 3H), 7.36 (q, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.07 (s, 2H), 3.89 (t, 2H), 3.83 (s, 2H), 3.66-3.55 (m, 4H), 3.30 (s, 1H), 3.08 (s, 4H), 3.02 (t, 2H), 2.22 (d, 2H), 2.10 (s, 3H), 1.97-1.78 (m, 2H), 1.44 (s, 2H), 1.31 (q, 4H), 1.20-0.96 (m, 6H), 0.87 (s, 6H). MS (ESI) m/e 887.3 (M+H)+.
A solution of Example 1.2. 7 (0.055 g,), tert-butyl 2-( 4-oxopiperidin-1-yl)acetate (0.014 g)and sodium triacetoxyborohydride (0.019 g) was stirred in dichloromethane (0.5 mL) at roomtemperature. After stirring for 2 hours, trifluoroacetic acid (0.5 mL) was added to the reaction, andstirring was continued overnight. The reaction was concentrated, dissolved in N,N-25 dimethylformamide (1.5 mL) and water (0.5 mL) and purified by reverse phase HPLC using a Gilsonsystem, eluting with 10-80% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. Thedesired fractions were combined and freeze-dried to provide the title compound. 1H NMR (501 MHz,dimethyl sulfoxide-d6) 8 ppm 12.85 (s, 1H), 8.80 (s, 2H), 8.03 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H),7.55-7.41 (m, 3H), 7.36 (q, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.07 (s, 2H), 3.89 (t, 2H),30 3.83 (s, 2H), 3.66-3.55 (m, 4H), 3.30 (s, 1H), 3.08 (s, 4H), 3.02 (t, 2H), 2.22 (d, 2H), 2.10 (s, 3H),1.97-1.78 (m, 2H), 1.44 (s, 2H), 1.31 (q, 4H), 1.20-0.96 (m, 6H), 0.87 (s, 6H). MS (ESI) m/e 887.3(M+Ht.
A solution of Example 1.2.7 (0.055 g,), <strong>[149554-03-0]tert-butyl 2-(4-oxopiperidin-1-yl)acetate</strong> (0.014 g) and sodium triacetoxyborohydride (0.019 g) was stirred in dichloromethane (0.5 mL) at room temperature. After stirring for 2 hours, trifluoroacetic acid (0.5 mL) was added to the reaction, and stirring was continued overnight. The reaction was concentrated, dissolved in N,N-dimethylformamide (1.5 mL) and water (0.5 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 10-80% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. 1H NMR (501 MHz, dimethyl sulfoxide-d6) delta ppm 12.85 (s, 1H), 8.80 (s, 2H), 8.03 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.55-7.41 (m, 3H), 7.36 (q, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.07 (s, 2H), 3.89 (t, 2H), 3.83 (s, 2H), 3.66-3.55 (m, 4H), 3.30 (s, 1H), 3.08 (s, 4H), 3.02 (t, 2H), 2.22 (d, 2H), 2.10 (s, 3H), 1.97-1.78 (m, 2H), 1.44 (s, 2H), 1.31 (q, 4H), 1.20-0.96 (m, 6H), 0.87 (s, 6H). MS (ESI) m/e 887.3 (M+H)+.

  • 10
  • [ 41661-47-6 ]
  • [ 5292-43-3 ]
  • [ 149554-03-0 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; for 4.0h; To the solution of piperidin-4-one (10 mmol) inTHF (20 mL) was added tert-Butyl bromoacetate (11 mmol), and the mixture was stirredfor 4 h. The mixture was poured to H20 and extracted with EtOAc (3X). The combined organic was washed with brine, dried with Na2504. The solvent was removed under vacuum to afford the crude amineketone, which was used for next step without purification. To the suspension of crude amineketone (1 mmol) in CH2C12 was addedm-CPBA (2 mmol) at 0 C. The mixture was stirred for 8 h at room temp. The aqueous Na2 S203 was added and the mixture was extracted with CH2C12, washed with brine and dried with Na2504. The solvent was removed under vacuum, and the residual was purified with flash column (MeOH : CH2C12 1:4) to give desired lactone (40% for 3 steps).
  • 11
  • [ 149554-03-0 ]
  • C11H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 8.0h; To the solution of piperidin-4-one (10 mmol) inTHF (20 mL) was added tert-Butyl bromoacetate (11 mmol), and the mixture was stirredfor 4 h. The mixture was poured to H20 and extracted with EtOAc (3X). The combined organic was washed with brine, dried with Na2504. The solvent was removed under vacuum to afford the crude amineketone, which was used for next step without purification. To the suspension of crude amineketone (1 mmol) in CH2C12 was addedm-CPBA (2 mmol) at 0 C. The mixture was stirred for 8 h at room temp. The aqueous Na2 S203 was added and the mixture was extracted with CH2C12, washed with brine and dried with Na2504. The solvent was removed under vacuum, and the residual was purified with flash column (MeOH : CH2C12 1:4) to give desired lactone (40% for 3 steps).?H NMR (400 MHz, CDC13) 1.47 (s, 9H), 2.52 (t, J = 7.9 Hz, 2H), 2.94 t, J =7.9 Hz, 2H), 3.26 (s, 2H), 3.80 (m, 2H), 4.25 (m, 2H).
 

Historical Records

Technical Information

Categories