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Quality Control of [ 40318-15-8 ] Purity: 95% SDS Specification

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Product Details of [ 40318-15-8 ]

CAS No. :	40318-15-8
Formula :	C₇H₉NO₂
M.W :	139.15
SMILES Code :	O=C(C1=CNC=C1C)OC
MDL No. :	MFCD10565693
InChI Key :	CXMYWJRJTQUXQD-UHFFFAOYSA-N
Pubchem ID :	15274278

Safety of [ 40318-15-8 ]

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

Computational Chemistry of [ 40318-15-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	37.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.09 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.68
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.11
Log P_o/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.	0.37
Log P_o/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	1.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.15

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.53
Solubility	4.14 mg/ml ; 0.0297 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.	-1.4
Solubility	5.54 mg/ml ; 0.0398 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	-2.04
Solubility	1.26 mg/ml ; 0.00906 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.	-6.49 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)	1.42

Application In Synthesis of [ 40318-15-8 ]

* 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 [ 40318-15-8 ]

[ 40318-15-8 ] Synthesis Path-Downstream 1~31

1
[ 186581-53-3 ]
[ 64276-66-0 ]
[ 40318-15-8 ]

References: [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392.
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855.

2
[ 40318-15-8 ]
[ 79-22-1 ]
4-Methyl-pyrrole-1,3-dicarboxylic acid dimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 9649 - 9652.

3
[ 623-43-8 ]
[ 38622-91-2 ]
[ 40318-15-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3.5h;	Reference Example 1 Methyl 4-methyl-1H-pyrrole-3-carboxylate To a suspension of potassium tert-butoxide (76.7 g) in tetrahydrofuran (900 mL) was added dropwise a solution of p-toluenesulfonylmethyl isocyanide (94.6 g) and methyl crotonate (48.5 g) in tetrahydrofuran (900 mL) over 30 min. The reaction mixture was stirred at room temperature for 3 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give the title compound as a white solid (yield 16.8 g, 25%). 1H-NMR (CDCl3) delta: 2.29 (3H, s), 3.80 (3H, s), 6.53-6.54 (1H, m), 7.36-7.38 (1H, m), 8.25 (1H, brs).

References: [1]Patent: EP2005957,2008,A1 .Location in patent: Page/Page column 44.
[2]Tetrahedron Letters,1994,vol. 35,p. 9649 - 9652.
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1429 - 1433.

Yield	Reaction Conditions	Operation in experiment
25%	With potassium tert-butylate; In tetrahydrofuran; at 10 - 35℃; for 1.5h;	General procedure: Reference Example 39 Methyl 1H-pyrrole-3-carboxylate A solution (250 mL) of p-toluenesulfonylmethyl isocyanide (15.0 g) and methyl acrylate (6.92 mL) in tetrahydrofuran was added dropwise to a suspension (100 mL) of potassium tert-butoxide in tetrahydrofuran over 30 min. The reaction mixture was stirred at room temperature for 1 hr, and filtered through a glass filter filled with silica gel (diameter 8 cm, height 4 cm), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1?2:1) to give the title compound as a pale-yellow solid (yield 4.69 g, 49%). 1H-NMR (CDCl3)delta: 3.82 (3H, s), 6.15 (1H, m), 6.75 (1H, m), 7.43 (1H, m), 8.50 (1H, brs).
		Reference Example 88 Methyl 4-methyl-1H-pyrrole-3-carboxylate Using p-toluenesulfonylmethyl isocyanide (94.6 g), methyl crotonate (48.5 g) and potassium tert-butoxide (76.7 g), a procedure as in Reference Example 39 was performed to give the title compound as a pale-yellow solid (yield 16.8 g, 25%). 1H-NMR (CDCl3)delta: 2.29 (3H, s), 3.80 (3H, s), 6.53-6.54 (1H, m), 7.36-7.38 (1H, m), 8.25 (1H, brs).

5
(E)-3-(2-Bromo-allylamino)-acrylic acid methyl ester [ No CAS ]
[ 40318-15-8 ]

References: [1]Chemical Communications,2000,p. 873 - 874.

6
[ 40318-15-8 ]
[ 76-02-8 ]
methyl 4-methyl-5-(2,2,2-trichloroacetyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; In 1,2-dichloro-ethane; at -40 - 20℃; for 48h;Inert atmosphere;	To a suspension of aluminum chloride (51.16 g, 384 mmol) in DCE (200 mL) was added trichloroacetyl chloride (43 mL, 384mmol) dropwise at -40 C under nitrogen atmosphere, followed by a solution of compound 1 (10.6 g, 76.7 mmol) in DCE (50 mL). The reaction mixture was gradually warmed to rt and stirred for 2 days. The mixture was poured into ice-water carefully and extracted with CH2Cl2. The combined organic layer was washed with 3 N HCl, brine, dried over anhydrous Na2SO4, and filtered. The solvent was evaporated in vacuo to afford 2 (20.3 g, 94 %) as a dark oil which was used for next step without further purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1429 - 1433.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3700 - 3705.

7
[ 40318-15-8 ]
[ 310431-26-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1429 - 1433.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3700 - 3705.

8
[ 40318-15-8 ]
4-[(3-Hydroxyphenyl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester [ No CAS ]