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Chemical Structure| 27550-90-9 Chemical Structure| 27550-90-9

Structure of 27550-90-9

Chemical Structure| 27550-90-9

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Product Details of [ 27550-90-9 ]

CAS No. :27550-90-9
Formula : C5H11NO
M.W : 101.15
SMILES Code : CC1CNCCO1
MDL No. :MFCD08444368

Safety of [ 27550-90-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H226
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
Class:8(3)
UN#:2734
Packing Group:

Computational Chemistry of [ 27550-90-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 31.84
TPSA ?

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

21.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.68
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

-0.14
Log Po/w (WLOGP)?

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

-0.39
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.

-0.16
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

1.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.42

Water Solubility

Log S (ESOL):?

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

-0.38
Solubility 42.3 mg/ml ; 0.418 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.

0.15
Solubility 142.0 mg/ml ; 1.4 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-0.86
Solubility 13.9 mg/ml ; 0.138 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

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
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.

-7.02 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

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)

1.61

Application In Synthesis of [ 27550-90-9 ]

* 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 [ 27550-90-9 ]

[ 27550-90-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 27550-90-9 ]
  • isobutyl chioroformate [ No CAS ]
  • [ 6638-79-5 ]
  • [ 78190-11-1 ]
  • [ 405239-72-7 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; To a cooled (-15 C. to -20 C.) and stirred solution of <strong>[78190-11-1]1-[(benzyloxy)carbonyl]-3-piperidinecarboxylic acid</strong> (4.0 g, 15.2 mmol) in dry THF (50 mL) including methylmorpholine (2 mL) was added dropwise a solution of isobutyl chioroformate (2.28 g, 16.7 mmol) in THF (10 mL). After the mixture was stirred at the same temperature for 20 min, a solution of N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.7 mmol) in THF (20 mL) including methylmorpholine (2 mL) was added. The reaction mixture was allowed to warm to room temperature, and then stirred for 16 hrs. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The separated organic phase was washed with 1N HCl, saturated NaHCO3, and brine, successively. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give benzyl 3-[methoxy(methyl)amino]carbonyl)-1-piperidinecarboxylate as a colorless oil (4.7 g, yield; quant.).
  • 2
  • [ 27550-90-9 ]
  • [ 2972-52-3 ]
  • (2,4-dichloropyrimidin-5-yl)(2-methylmorpholino)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 2h; (a) (2,4-dichloropyrimidin-5-yl')(2-methylmorpholino')methanone (compound 3) Phosphorus pentachloride (128.1 g, 0.615 mol) was added portionwise to a stirred mixture of 2,4-dihydroxypyrimidine-5-carboxylic acid (compound 1) (26.7 g, 171 mmol, Alfa Aesar) in phosphorous oxychloride (122.2 ml_, 1.29 mol) at RT. The reaction mixture was heated to 115 C and stirred overnight. The reaction was cooled to RT and the volatiles were removed under vacuum. The residue was diluted with cyclohexane and filtered. The filtrate was evaporated under reduced pressure to give <strong>[2972-52-3]2,4-dichloropyrimidine-5-carbonyl chloride</strong> (compound 2) as a yellow oil (37.9 g). This material was used in the next step without further purification. A solution of 2-methylmorpholine (Intermediate B) (4.91 g, 48.6 mmol, Enamine) and DIPEA (8.5 ml_, 48.8 mmol) in DCM (60 ml.) was added dropwise over 30 minutes to a stirred solution of <strong>[2972-52-3]2,4-dichloropyrimidine-5-carbonyl chloride</strong> (compound 2) (9.34 g, 44.2 mmol) in DCM (242 ml.) at 0 C. The reaction mixture was stirred for 2 h at 0 C and then quenched with H20. The phases were separated and the organic phase washed with 0.5 M HCI, H20, dried over Na2S04 and then evaporated under reduced pressure. The residue was purified by flash column chromatography (Cyclohexane/EtOAc 6/4 to 4/6) to give desired (2,4- dichloropyrimidin-5-yl)(2-methylmorpholino)methanone (compound 3) as a colourless oil which solidified on standing (11.02 g, 90% yield). It will be appreciated by the skilled artisan that the above reaction may be carried out using 2-methylmorpholine hydrochloride salt (Intermediate B, hydrochloride salt), in which case an extra one equivalent of base (DIPEA) may be used in the reaction. Alternatively, 2-methylmorpholine hydrochloride salt may be converted to 2-methylmorpholine free base by treatment with a suitable base (e.g. DIPEA) prior to being employed in the reaction. MS (+ve ion electrospray): m/z 276 [MH+]
 

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