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Chemical Structure| 68832-13-3 Chemical Structure| 68832-13-3

Structure of 68832-13-3

Chemical Structure| 68832-13-3

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Product Details of [ 68832-13-3 ]

CAS No. :68832-13-3
Formula : C5H11NO
M.W : 101.14
SMILES Code : OC[C@@H]1NCCC1
MDL No. :MFCD00064321
InChI Key :HVVNJUAVDAZWCB-RXMQYKEDSA-N
Pubchem ID :2724541

Safety of [ 68832-13-3 ]

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

Computational Chemistry of [ 68832-13-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 31.91
TPSA ?

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

32.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.39
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

-0.33
Log Po/w (WLOGP)?

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

-0.65
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

0.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.19

Water Solubility

Log S (ESOL):?

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

-0.19
Solubility 64.8 mg/ml ; 0.641 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.

0.11
Solubility 131.0 mg/ml ; 1.3 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

-0.56
Solubility 27.7 mg/ml ; 0.274 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

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.

-7.15 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)

1.38

Application In Synthesis of [ 68832-13-3 ]

* 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 [ 68832-13-3 ]

[ 68832-13-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 68832-13-3 ]
  • [ 501-53-1 ]
  • [ 72597-18-3 ]
YieldReaction ConditionsOperation in experiment
100% [Example 68] 3-((2R)-1-[((2S)-1'-{2-[(2R)-4-[3,5-bis(Trifluoromethyl)benzoyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl)oxy]acetyl}pyrralidin-2-yl)propan-1-ol hydrochloride (Exemplary compound No. 2-574 hydrochloride) [Example 68a] Benzyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 2 g (0.0198 mol) of (2R)-pyrrolidin-2-ylmethanol was dissolved in 20 mL of ethyl acetate, 20 mL of water was added thereto, and the mixture was stirred. 3.3 g (0.30 mol) of sodium hydrogencarbonate was added to the mixture, followed by stirring of the mixture for 5 minutes. 4.24 mL (0.03 mol) of benzyl chloroformate was added dropwise to the mixture, followed by stirring for 5 hours. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to quantitatively obtain the title compound. 1H-NMR spectrum (500 MHz, CDCl3) delta ppm: 7.55-7.28 (5H, m), 5.16 (2H, s), 4.12-3.90 (1H, br), 3.83-3.33 (4H, m), 2.19-1.51 (4H, m).
In diethyl ether; EXAMPLE 51 (R)-2-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1-pyrrolidinecaboxylic acid phenylmethyl ester The title compound is prepared by the procedure of Example 50 using 20.0 g of (R)-2-pyrrolidinemethanol, 44.0 g of benzyl chloroformate and 200 ml of diethyl ether to give 56.4 g of (R)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenyl methyl ester.
  • 2
  • [ 13139-17-8 ]
  • [ 68832-13-3 ]
  • [ 72597-18-3 ]
  • 3
  • [ 1336-21-6 ]
  • [ 68832-13-3 ]
  • [ 3913-23-3 ]
  • [ 7087-68-5 ]
  • [ 346732-23-8 ]
YieldReaction ConditionsOperation in experiment
95% In water; N,N-dimethyl-formamide; a [(2R)-1-(2-Methoxy-5-Nitrobenzyl)Pyrrolidinyl]Methanol Hydrochloride To <strong>[3913-23-3]2-methoxy-5-nitrobenzyl bromide</strong> (6.11 g, 24.8 mmol) dissolved in N,N-dimethylformamide (25 mL) was added Hunig's base (3.5 g, 27.2 mmol) followed by R-(-)-2-pyrrolidinemethanol (2.4 g, 24.8 mmol) and the reaction mixture was stirred at room temperature for 16 h. The N,N-dimethylformamide was removed, the residue treated with water (100 mL) followed by aqueous ammonium hydroxide until basic and extracted with ethyl acetate (3*100 mL). The ethyl acetate extracts were combined, washed with water (3*100 mL), dried over magnesium sulphate, filtered, and evaporated to give the free base of the title compound as a yellow oil (6.0 g). Treatment of an ethanol solution of the free base with ethanol/hydrogen chloride afforded the title compound (7.4 g, 95%) as a light yellow solid; MS: m/z 267 [M+H]+.
  • 4
  • [ 4606-65-9 ]
  • [ 6457-49-4 ]
  • [ 103-76-4 ]
  • [ 50-00-0 ]
  • [ 63006-93-9 ]
  • [ 68832-13-3 ]
  • [ 18881-17-9 ]
  • [ 1107174-37-7 ]
  • [ 1106671-44-6 ]
  • [ 1106671-06-0 ]
  • C20H21BrN2O3 [ No CAS ]
  • C23H21NO3S2 [ No CAS ]
  • [ 1106671-83-3 ]
  • [ 1106671-48-0 ]
  • C22H21N3O3S [ No CAS ]
  • C25H20N2O3S [ No CAS ]
  • C27H23NO4S [ No CAS ]
  • C27H24N2O3S [ No CAS ]
  • C26H23N3O3S [ No CAS ]
  • C28H26N2O4S [ No CAS ]
  • [ 135980-88-0 ]
  • [ 124-40-3 ]
  • [ 74-89-5 ]
  • [ 23356-96-9 ]
  • [ 498-63-5 ]
  • [ 958451-07-5 ]
  • [ 958449-79-1 ]
  • [ 958451-09-7 ]
  • [ 958450-34-5 ]
  • [ 958451-15-5 ]
  • [ 958450-40-3 ]
  • [ 958450-35-6 ]
  • [ 958450-41-4 ]
  • [ 958451-11-1 ]
  • [ 958449-81-5 ]
  • [ 958449-68-8 ]
  • [ 958449-67-7 ]
  • [ 958449-66-6 ]
  • [ 958450-36-7 ]
  • [ 958450-37-8 ]
  • [ 958450-39-0 ]
  • [ 958449-76-8 ]
  • [ 958449-77-9 ]
  • [ 958449-71-3 ]
  • [ 958449-78-0 ]
  • [ 958450-38-9 ]
  • [ 958449-69-9 ]
  • [ 958449-75-7 ]
  • [ 958449-70-2 ]
  • [ 958449-80-4 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; at 70 - 80℃; for 12 - 48h;Combinatorial reaction / High throughput screening (HTS); Example 1. Preparation of a combinatorial library of substituted 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids esters of general formula 1.1. A mixture of 0.357 mmol of ester 2, 0.43 mmol of a secondary amine 3, and 0.43 mmol of formaldehyde in the form of formalin in 3 ml of dioxane is heated at 70-80°C at stirring for 12 to 48 hours. Progress of the reaction is monitored by chromato-mass-spectrometry. Upon completion of the reaction, the reaction mass is diluted with water, the residue is filtered and recrystallized from a suitable solvent, or purified by chromatography.
  • 5
  • [ 68832-13-3 ]
  • [ 54287-92-2 ]
  • (R)-2-(hydroxymethyl)-N-(pyridin-4-yl)pyrrolidine-1-carboxamide [ No CAS ]
  • 6
  • [ 848398-41-4 ]
  • [ 68832-13-3 ]
  • (R)-(1-(2-chloro-5,7-dihydrofuro[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 50℃; for 5h; General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 - 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 - 3.82 (m, 1H), 3.72 - 3.39 (m, 2H), 2.22 - 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).
  • 7
  • [ 848398-41-4 ]
  • [ 68832-13-3 ]
  • (R)-(1-(2-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-5,7-dihydrofuro[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
  • 8
  • [ 18740-39-1 ]
  • [ 68832-13-3 ]
  • (R)-(1-(2-chlorothieno[2,3-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 20℃; for 2h; General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 °C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 percent yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 - 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 - 3.82 (m, 1H), 3.72 - 3.39 (m, 2H), 2.22 - 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).
  • 9
  • [ 18740-39-1 ]
  • [ 68832-13-3 ]
  • (R)-(1-(2-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)thieno[2,3-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
 

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