52867-42-2|Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate| Ambeed

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Quality Control of [ 52867-42-2 ] Purity: 95% SDS Specification

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Product Details of [ 52867-42-2 ]

CAS No. :	52867-42-2
Formula :	C₆H₈N₂O₃
M.W :	156.14
SMILES Code :	O=C(C1=CC(NN1C)=O)OC
MDL No. :	MFCD00459835
InChI Key :	IYAQFZAPKKWPNU-UHFFFAOYSA-N
Pubchem ID :	304501

Safety of [ 52867-42-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 52867-42-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	37.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
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	-0.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.5
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.	-0.13
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	0.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.97
Solubility	16.8 mg/ml ; 0.108 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.	-0.82
Solubility	23.4 mg/ml ; 0.15 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	-0.77
Solubility	26.7 mg/ml ; 0.171 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.	-7.3 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)	1.86

Application In Synthesis of [ 52867-42-2 ]

* 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 [ 52867-42-2 ]

[ 52867-42-2 ] Synthesis Path-Downstream 1~41

1
[ 58364-79-7 ]
[ 1072-91-9 ]
[ 85963-51-5 ]
[ 52867-42-2 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1520 - 1524.

2
[ 58364-79-7 ]
[ 85963-51-5 ]
[ 51985-95-6 ]
[ 52867-42-2 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1525 - 1530.

3
[ 58364-79-7 ]
[ 52867-42-2 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1520 - 1524.

4
[ 58364-79-7 ]
[ 542-92-7 ]
[ 1072-91-9 ]
[ 947-57-9 ]
[ 52867-42-2 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1520 - 1524.

5
[ 762-42-5 ]
[ 60-34-4 ]
[ 52867-42-2 ]

Yield	Reaction Conditions	Operation in experiment
23%	In methanol; water; at 70℃;	To a solution of dimethyl acetylenedicarboxylate (5 g, 35.18 mmol) in methanol (25 mL)-water (2.5mL) was added dropwise methylhydrazine (1.945 g, 42.22 mmol) at room temperature. The reaction mixture was stirred at 70C overnight, cooled to room temperature, concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (90:10-3:4)] to give the title compound (1.26 g) as a colorless oil (yield 23%). MS (ESI+): [M+H]+157. 1H NMR (300 MHz, DMSO-d6) delta 3.79 (3H, s), 3.88 (3H, s), 6.00 (1H, s), 10.06 (1H, s).
5 g	In methanol; water; at 0 - 70℃; for 10h;	The compound methyl hydrazine (10g) was dissolved in methanol (20mL) and water (10mL), cooled to 0 degree, stirred for 15min, then compound 21 (12g) was added dropwise to the reaction system, heated to 70 degrees for 10h, then the system temperature was returned to room temperature, the reaction 12h, filtered off with suction, the filter cake was washed with water (5mL), dried to give 22 as a pale yellow solid 5g
5 g	In methanol; water; at 0 - 70℃; for 10.25h;	The compound methyl hydrazine (10 g) was dissolved in methanol (20 mL) and water (10 mL).The temperature was lowered to 0 , stirred for 15 min, and then Compound 21 (12 g) was added dropwise to the reaction system.Heat to 70 for 10 h, then return the system temperature to room temperature.After 12 h of reaction, suction filtration, and the filter cake was washed with water (5 mL).Get 22 pale yellow solids 5g

References: [1]Patent: EP2530078,2012,A1 .Location in patent: Page/Page column 208-209.
[2]Chemische Berichte,1988,vol. 121,p. 2007 - 2012.
[3]Patent: CN108250122,2018,A .Location in patent: Paragraph 0312-0316.
[4]Patent: CN108264520,2018,A .Location in patent: Paragraph 0193; 0194; 0195; 0196; 0197.

6
[ 58364-79-7 ]
[ 123-54-6 ]
[ 1072-91-9 ]
[ 85963-51-5 ]
[ 52867-42-2 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1520 - 1524.

9
[ 105-36-2 ]
[ 52867-42-2 ]
[ 58365-08-5 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1434 - 1447.

10
[ 135-73-9 ]
[ 52867-42-2 ]
[ 692259-01-1 ]