Home Cart Sign in  
Chemical Structure| 85275-45-2 Chemical Structure| 85275-45-2

Structure of 85275-45-2

Chemical Structure| 85275-45-2

*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 [ 85275-45-2 ]

CAS No. :85275-45-2
Formula : C10H19NO3
M.W : 201.26
SMILES Code : O=C(N1CC(O)CCC1)OC(C)(C)C
MDL No. :MFCD02093938
InChI Key :UIJXHKXIOCDSEB-UHFFFAOYSA-N
Pubchem ID :545699

Safety of [ 85275-45-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 85275-45-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.9
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 57.75
TPSA ?

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

49.77 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.41
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

0.98
Log Po/w (WLOGP)?

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

1.0
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.

0.86
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

0.56
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.16

Water Solubility

Log S (ESOL):?

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

-1.51
Solubility 6.26 mg/ml ; 0.0311 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.

-1.61
Solubility 4.9 mg/ml ; 0.0244 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

-0.7
Solubility 39.8 mg/ml ; 0.198 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.

-6.83 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)

2.67

Application In Synthesis of [ 85275-45-2 ]

* 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 [ 85275-45-2 ]

[ 85275-45-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 574745-97-4 ]
  • [ 85275-45-2 ]
  • [ 612501-69-6 ]
YieldReaction ConditionsOperation in experiment
53% With triphenylphosphine; diethylazodicarboxylate; In dichloromethane; toluene; at 20 - 40℃; The4-chloro-7-methoxy-6-[1- (tert-butoxycarbonyl) piperidin-3-yloxy) ] quinazoline starting material was prepared as follows: Diethyl azodicarboxylate (9. 41ml, 40% solution in toluene) was added to a mixture of <strong>[574745-97-4]4-chloro-6-hydroxy-7-methoxyquinazoline</strong> (2.90g ; prepared as described in Example 16- preparation of starting materials), triphenylphosphine (5.43g) and tert-butoxycarbonyl-3- hydroxypiperidine (4.15g) in dichloromethane (75ml). The resulting solution was heated to 40C for 6 hours, and then allowed to stand overnight at room temperature. This was purified by flash column chromatography eluting with isohexane (79%), acetone (20%), and triethylamine (1%) to give 4-chloro-7-methoxy-6- [l- tert-butoxycarbonyl) piperidin-3- yloxy] quinazoline as a white solid (2.47g, 53%) ; 1H NMR Spectrum : (CDC13) 1. 5 (m, 9H) ; 1.6 (m, 1H); 1.9 (m, 2H) ; 2.1 (m, 1H); 3.5 (m, 1H); 3.6 (m, 1H); 4.0 (s, 3H); 4.2-3. 9 (m, 2H) ; 4.5 (m, 1H); 7.3 (s, 1H) ; 7.4 (s, 1H); 8.9 (s, lH) ; Mass Spectrum : (M+H) : 394.
  • 2
  • [ 2040-90-6 ]
  • [ 85275-45-2 ]
  • 2-fluoro-5-(2-piperazin-1-yl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was prepared using Mitsunobu followed by Buchwald condition from <strong>[2040-90-6]2-chloro-6-fluoro phenol</strong> and racemic N-boc-3-hydroxypiperidine. MS found 380.3 M+1
  • 3
  • [ 7651-82-3 ]
  • [ 85275-45-2 ]
  • [ 1269630-45-6 ]
  • 4
  • [ 85275-45-2 ]
  • [ 124-63-0 ]
  • [ 940890-90-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 5℃; for 1h; Triethylamine (15.1 g) and methane sulfonyl chloride (6.26 g) was slowly added to a solution of N-Boc-3-hydroxy piperidine (10 g) in dichloromethane (200 mL) at 0-5 °C. The mixture was stined for 60 mm at 0-5 °C and water (200 mL) was added. The layers were separated and the organic layer was washed with water (200 mL) and concentrated to give tert-butyl-(S)-3- ((methylsulfonyl)oxy)piperidine- 1 -carboxylate.
  • 5
  • [ 3512-75-2 ]
  • [ 85275-45-2 ]
  • C17H26N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 50℃; for 60h; Sodium hydride (1 g, 25 mmol) was added to 1-Boc-3-hydroxypiperidine (CAS:85275-45-2; 5 g, 25 mmol) in DMF (100 mL) at 0 °C. The mixture was allowed to warm to rt and then it was cooled again to 0 °C. A solution of 2,6-dimethyl-4- chloropyridine (CAS: 35 12-75-2; 3.52 g, 25 mmol) in DMF (10 mL) was addeddropwise. The mixture was stirred at 50 °C for 60 h. Then the mixture was cooled to rt. Water was added and the mixture was extracted with EtOAc. The organic layer was dried over Mg504, filtered and evaporated under vacuum. The resulting residue was purified by flash chromatography (silica gel, DCM, 1percent MeOH in DCM, 2percent, 4percent) The pure fractions were evaporated under vacuum affording intermediate 1 (2.52 g, 33percent).
  • 6
  • [ 85275-45-2 ]
  • [ 205444-22-0 ]
  • C16H20ClF3N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% In N,N-dimethyl-formamide; at 20℃; for 16h; To a stirred solution of tert- butyl 3-hydroxy- l-piperidinecarboxylate (2500 mg, 12.42 mmol) in DMF (10 mL) at -40 C, was added 2-chloro-4-iodo-6-trifluoromethyl- pyridine (CAS 205444-22-0, 3.62 g, 12.42 mmol) in DMF (4 mL) dropwise. The mixture was gradually warmed to rt and stirred for 16 h. The mixture was diluted with EtOAc and washed with H20 and brine. The organic layer was separated, dried (Na2S04), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to yield intermediate 26 (2.8 g, 59%) as a light- yellow oil.
59% Sodium hydride (CAS: 7646-69-7; 60% dispersion in mineral oil, 0.50 g, 12.42 mmol) was added to a stirred solution of l-Boc-3-hydroxypiperidine (CAS: 85275-45-2; 2.5 g, 12.42 mmol) in DMF (14 mL) at -40 C. The mixture was stirred at -40 C for 30 min and then a solution of <strong>[205444-22-0]2-chloro-4-iodo-6-trifluoromethylpyridine</strong> (CAS: 205444-22-0; 3.82 g, 12.42 mmol) in DMF (4 mL) was added dropwise. The mixture was allowed to warm to rt and then was stirred for 16 h. Then the mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried (Na2S04), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica; EtOAc in heptane, gradient from 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to yield intermediate 4d as a light-yellow oil (2.8 g, 59%).
  • 7
  • [ 38557-72-1 ]
  • [ 85275-45-2 ]
  • C16H25N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; mineral oil; at 60℃; General procedure: l-Boc-3-hydroxypiperidine (CAS 85175-45-2, 0.41 g, 2.05 mmol) was stirred in DMF (1.65 mL), at rt, and then a 60% NaH dispersion in mineral oil (0.082 g, 2.05 mmol) was added. Then 4-chloro-2,6-dimethylpyridine (CAS 3512-75-2, 0.26 mL, 2.05 mmol) in DMF (0.64 mL) was added dropwise at rt. The mixture was stirred overnight at 60 C. The mixture was evaporated diluted with FLO and was extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and evaporated, in vacuo. The residue was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 30/70). The desired fractions were collected and concentrated in vacuo to yield intermediate 22 (0.32 g, 51%) as a colorless oil(0656) Intermediate 129 was prepared following an analogous procedure to the one described for the synthesis of intermediate 22 using <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong> (CAS 38557- 72-1) as starting material and THF as solvent.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 85275-45-2 ]

Alcohols

Chemical Structure| 143900-44-1

A118676 [143900-44-1]

(S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 143900-43-0

A185071 [143900-43-0]

(R)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 443955-98-4

A129292 [443955-98-4]

(3R,4R)-rel-tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 301221-57-8

A335785 [301221-57-8]

tert-Butyl 4-(2-amino-1-hydroxyethyl)piperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 114676-61-8

A311614 [114676-61-8]

(2S,4R)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

Similarity: 0.91

Amides

Chemical Structure| 143900-44-1

A118676 [143900-44-1]

(S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 143900-43-0

A185071 [143900-43-0]

(R)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 443955-98-4

A129292 [443955-98-4]

(3R,4R)-rel-tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 301221-57-8

A335785 [301221-57-8]

tert-Butyl 4-(2-amino-1-hydroxyethyl)piperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 1171125-92-0

A217936 [1171125-92-0]

(3S,4R)-tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylate

Similarity: 0.91

Related Parent Nucleus of
[ 85275-45-2 ]

Piperidines

Chemical Structure| 143900-44-1

A118676 [143900-44-1]

(S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 143900-43-0

A185071 [143900-43-0]

(R)-tert-Butyl 3-hydroxypiperidine-1-carboxylate

Similarity: 1.00

Chemical Structure| 443955-98-4

A129292 [443955-98-4]

(3R,4R)-rel-tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 301221-57-8

A335785 [301221-57-8]

tert-Butyl 4-(2-amino-1-hydroxyethyl)piperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 1171125-92-0

A217936 [1171125-92-0]

(3S,4R)-tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylate

Similarity: 0.91