Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 77497-84-8 Chemical Structure| 77497-84-8

Structure of 77497-84-8

Chemical Structure| 77497-84-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 77497-84-8 ]

CAS No. :77497-84-8
Formula : C7H13NO2
M.W : 143.18
SMILES Code : O=C(OC)CCNC1CC1
English Name :Methyl 3-(cyclopropylamino)propanoate
MDL No. :MFCD11651272
InChI Key :IXRSFGOAMNXZBZ-UHFFFAOYSA-N
Pubchem ID :13041902

Safety of [ 77497-84-8 ]

Computational Chemistry of [ 77497-84-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.86
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 37.74
TPSA ?

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

38.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.16
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

0.73
Log Po/w (WLOGP)?

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

0.24
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.

0.35
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

0.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.86

Water Solubility

Log S (ESOL):?

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

-0.86
Solubility 19.9 mg/ml ; 0.139 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.

-1.11
Solubility 11.0 mg/ml ; 0.077 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

-1.39
Solubility 5.79 mg/ml ; 0.0405 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.

-6.66 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)

1.24

Application In Synthesis of [ 77497-84-8 ]

* 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 [ 77497-84-8 ]

[ 77497-84-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 96-33-3 ]
  • [ 765-30-0 ]
  • [ 194468-47-8 ]
  • [ 77497-84-8 ]
YieldReaction ConditionsOperation in experiment
With benzoic acid; isopentyl nitrite In chloroform at 5℃; for 40h; Title compound not separated from byproducts;
  • 2
  • [ 65973-52-6 ]
  • [ 77497-84-8 ]
  • [ 82301-02-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene 20.a (a) (a) 6-Chloro-4-(N-2-methoxycarbonylethyl-N-cyclopropyl)-amino-pyridine-3-carboxylic acid methyl ester (a compound of formula (VI) in which R=methyl and X=chlorine). A mixture of 28.6 g of β-cyclopropylamino-propionic acid methyl ester and 21 g of triethylamine was rapidly added dropwise to a solution of 41.2 g of 4,6-dichloropyridine-3-carboxylic acid methyl ester in 150 ml of toluene at 10° to 20° C., whilst cooling with ice and stirring. The ice-bath was removed and the mixture was stirred at room temperature for 1/2 hour and heated to the boiling point under reflux for 6 hours. The resulting suspension was washed with water and dried with Na2 SO4 and the solvent was distilled off in vacuo. 59 g of the title compound were obtained as a brown oil.
With triethylamine In toluene 20.a (a) (a) 6-Chloro-4-(N-2-methoxycarbonylethyl-N-cyclopropyl)-amino-pyridine-3-carboxylic acid methyl ester (a compound of formula (VI) in which R=methyl and X=chlorine). A mixture of 28.6 g of β-cyclopropylamino-propionic acid methyl ester and 21 g of triethylamine was rapidly added dropwise to a solution of 41.2 g of 4,6-dichloropyridine-3-carboxylic acid methyl ester in 150 ml of toluene at 10° to 20° C., whilst cooling with ice and stirring. The ice-bath was removed and the mixture was stirred at room temperature for 1/2 hour and heated to the boiling point under reflux for 6 hours. The resulting suspension was washed with water and dried with Na2 SO4 and the solvent was distilled off in vacuo. 59 g of the title compound were obtained as a brown oil.
  • 3
  • [ 765-30-0 ]
  • [ 140-88-5 ]
  • [ 77497-84-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20℃; 20 Compound 20: 4-(9-cyclopropyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5- b] [ 1 ,4] diazepin-2-ylamino)-3 -methoxy-iV-( 1 -methylpiperidin-4-yl)benzamide; [0336] The title compound was synthesized using an analogous procedure to that described in connection with Compound 11 except that methyl 3-(cyclopropylamino)propanolate, prepared by Michael addition of ethyl acrylate (1 equiv.) with cyclopropylamine (1 equiv.) in ethanol overnight (see Scheme 2), was used and the final compound was purified by reverse phase HPLC to yield the TFA salt. 1H NMR (400 MHz, DMSO-J6) δ 0.7 (m, 2H), 0.88 (m, 2H), 1.77 (m, 2H), 2.01 (m, 2H), 2.67 (m, 2H), 2.79 (d. J=8 Hz, 3H), 2.93 (m, IH), 3.12 (overlap m&s, 5H), 3.47 (d, J=12 Hz, 2H), 3.80 (m, 2H), 3.96 (s, 3H), 4.14 (m, IH), 7.54 (overlap d & s, 2H), 8.18 (s, IH), 8.35 (d, J=8 Hz, IH), 8.50 (br s, IH), 8.64 (d, J=8 Hz, IH), 9.42 (br s, IH). [M+H] calc'd for C25H33N7O3 479; found, 479.
  • 4
  • [ 96-33-3 ]
  • [ 765-30-0 ]
  • [ 77497-84-8 ]
YieldReaction ConditionsOperation in experiment
92% With Ps-AlCl3 at 20℃; for 1.5h; chemoselective reaction; Aza-Michael addition General procedure: In a typical experiment, a mixture of amine (11 mmol), methacrylate or acrylonitrile (2 mmol), and Ps-AlCl3 (0.53 g, 0.24 mmol AlCl3 for aromatic amines; 0.27 g, 0.12 mmol AlCl3 for aliphatic amines) was stirred at 70 C for aromatic amines, room temperature for aliphatic amines. After completion of the reaction, Ps-AlCl3 was filtered and washed with ethyl acetate (3 10 ml), dried, and used in the next run under the same reaction conditions. The filtrate was concentrated to give the crude product, which was purified further by column chromatography (petroleum ether/ethylacetate or methanol/ethyl acetate).
14.2 g In ethanol at 20℃; for 10h; 3.1 (1) methyl 3-cyclopropylaminopropionate At room temperature, 8.6g (0.1mol) of methyl acrylate was slowly added dropwise 5.7g (0.1mol) cyclopropylamine in ethanol solution. Maintaining the reaction, it was stirred at room temperature for 10 hours. Distilled under reduced pressure gave 14.2g pale yellow oil. Was used directly without purification in the next step.
With Pseudomonas fluorescence lipase immobilized on hyroxypropyl methyl cellulose support In toluene at 50℃; for 3.5h; Enzymatic reaction; chemoselective reaction; 2.4. Reaction procedure and analysis General procedure: Various β-amino ester moieties were synthesized in a 10 mL glass reaction vessel of 1.2 cm i.d. with a glass lid. The desired Michael acceptor was taken into a reaction vessel and diluted by solvent. Afterwards, Michael donor was added into the reaction vessel and reaction was initiated by addition of immobilized HMC:PFL lipase very soon at a specified temperature. The sample of reaction mixture was analyzed by using gas chromatograph (Perkin Elmer Clarus: 400) having flame ionizing detector (FID) and capillary column. The detector and injector temperature were kept 280 and 50 °C, respectively. The oven temperature of GC was kept at 50 °C for 3 min constant and after that raised with 10 °C/min up to the 280 °C. Moreover, reaction products were also verified by GCMS (Gas-Chromatography-Mass Spectroscopy Shimadzu QP-2010) analysis.
In methanol at 20℃;

  • 5
  • [ 161949-73-1 ]
  • [ 77497-84-8 ]
  • [ 1960376-05-9 ]
YieldReaction ConditionsOperation in experiment
2.88 g With triethylamine In tetrahydrofuran at 20℃; for 2h; 3.2 (2) Synthesis of Compound 17 1.7g (0.012mol) methyl 3-cyclopropylaminopropionate and 1.52g (0.015mol) of triethylamine were added to 20ml of tetrahydrofuran. Stirring at room temperature, 3.90g (0.010mol) 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)benzene-1-sulfonylchloride and 20ml of tetrahydrofuran were added dropwise and the mixture was stirred at room temperature for 2 hours. Completion of the reaction was monitored by TLC. The mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was distilled under reduced pressure. The residue was subjected to column chromatography (ethyl acetate: petroleum ether = 1:5 ~ 1:2) to give 2.88g of Compound 17, as a white solid, m.p. 195.8°C.
  • 6
  • [ 77497-84-8 ]
  • [ 1182941-09-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 24 h / 20 °C 2: hydrogenchloride / water / 20 h / 20 °C
 

Historical Records

Technical Information

Categories