10234-66-9|1-Methyl-1H-pyrazol-5(4H)-one| Ambeed

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Quality Control of [ 10234-66-9 ] Purity: 97% SDS Specification

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Product Details of [ 10234-66-9 ]

CAS No. :	10234-66-9
Formula :	C₄H₆N₂O
M.W :	98.10
SMILES Code :	O=C1CC=NN1C
MDL No. :	MFCD20229439
InChI Key :	NNZXDXMEXBYSRF-UHFFFAOYSA-N
Pubchem ID :	10290752

Safety of [ 10234-66-9 ]

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

Computational Chemistry of [ 10234-66-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	0
Fraction Csp3	0.5
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	33.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.67 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.14
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	-0.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.93
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.	-0.49
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	0.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.07
Solubility	83.5 mg/ml ; 0.851 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.	0.39
Solubility	238.0 mg/ml ; 2.43 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	-0.05
Solubility	86.6 mg/ml ; 0.883 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.	-7.32 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	2.0
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)	2.38

Application In Synthesis of [ 10234-66-9 ]

* 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 [ 10234-66-9 ]

[ 10234-66-9 ] Synthesis Path-Downstream 1~20

1
[ 618-46-2 ]
[ 10234-66-9 ]
(3-Chloro-phenyl)-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1807 - 1812.

2
2,6-dimethyl-1-(2-methylpyrazol-1-io)-4-phenylpyridinium bistetrafluoroborate [ No CAS ]
[ 10234-66-9 ]
[ 52867-35-3 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5485 - 5488.
[2]Tetrahedron Letters,1985,vol. 26,p. 5485 - 5488.

3
[ 98-88-4 ]
[ 10234-66-9 ]
[ 109883-05-8 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1807 - 1812.

4
4,5-dihydro-5-oxo-1H-pyrazole4-carboxylic acid [ No CAS ]
[ 10234-66-9 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 810 - 820.

5
[ 529-23-7 ]
[ 10234-66-9 ]
[ 89522-17-8 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1539 - 1543.

6
[ 68-12-2 ]
[ 10234-66-9 ]
[ 117007-77-9 ]

References: [1]Journal of Organic Chemistry,1992,vol. <7> 57,p. 2127 - 2134.

7
[ 56074-73-8 ]
[ 10234-66-9 ]
2-Methyl-4-[1-[2-(3-methyl-but-2-enyloxy)-phenyl]-meth-(Z)-ylidene]-2,4-dihydro-pyrazol-3-one [ No CAS ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 810 - 820.

9
[ 67-56-1 ]
[ 137-44-0 ]
[ 10234-66-9 ]

References: [1]Synlett,2000,p. 809 - 810.

10
[ 7299-58-3 ]
[ 10234-66-9 ]
1-methyl-6-phenylpyrano[2,3-c]pyrazole-4-(1H)-one [ No CAS ]

References: [1]Synthesis,2005,p. 2583 - 2589.

Yield	Reaction Conditions	Operation in experiment
92.5%		EXAMPLE 3 Preparation of 1-methyl-2-pyrazolin-5-one, Work-up by Liquid-liquid Extraction As in Example 1, 10 g of 5-chloro-1-methylpyrazole-4-carboxylic acid were initially reacted with 100 g of 25% by weight strength aqueous sodium hydroxide solution and then under acidic conditions. The acidic reaction mixture was neutralized to pH 6.5 using 25% by weight strength aqueous sodium hydroxide solution and the reaction mixture was then transferred into a liquid-liquid extractor and extracted with isobutanol at the boiling point of the solvent. Isolation of the organic phase and distillative removal of the isobutanol gave 5.8 g of 1-methyl-2-pyrazolinone (purity according to GC: 98.1%). The melting point was 112 C. The yield was 92.5% of theory.

12
[ 54367-66-7 ]
[ 10234-66-9 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	In sodium hydroxide;	EXAMPLE 1 Preparation of 1-methyl-2-pyrazolin-5-one In a 250 ml autoclave, 10 g (0.0623 mol) of 5-chloro-1-methyl-4-pyrazolecarboxylic acid were dissolved in 100 g of 25% by weight strength aqueous sodium hydroxide solution (=0.623 mol). The solution was heated at 175 C. for 6 h. During this time, the pressure increased to 6 bar. After cooling, the autoclave was vented to atmospheric pressure. The reaction mixture was then adjusted to pH 1.5 using 60% by weight strength sulfuric acid. This resulted in evolution of CO2. After several minutes, the pH was adjusted to 6.5 using 25% by weight strength aqueous sodium hydroxide solution, and the resulting solution was concentrated under reduced pressure to dryness. The solid residue was transferred into a Soxhlet apparatus and continuously extracted with ethanol. Distillative removal of the ethanol under reduced pressure gave 5.7 g of the target compound of a purity of 98.9% (determined by gas chromatography). The melting point was 113 C. This corresponds to a yield of 92.3% of theory. The product was identified by the mixed melting point with an authentic sample.
92.3%	In sodium hydroxide;	EXAMPLE 13 Preparation of 1-methyl-2-pyrazolin-5-one 10 g (0.0623 mol) of 5-chloro-1-methyl-4-pyrazolecarboxylic acid were dissolved in 100 g of 25% by weight sodium hydroxide solution (=0.623 mol) in a 250 ml autoclave. The solution was heated at 175 C. for 6 h. The pressure rose to 6 bar during this. Cooling was followed by decompression to atmospheric pressure. The reaction mixture was then adjusted to pH 1.5 with 60% by weight sulfuric acid. CO2 evolution occurred during this. After a few minutes, the pH was adjusted to 6.5 with 25% by weight sodium hydroxide solution, and the resulting solution was evaporated to dryness in vacuo. The solid residue was transferred into a 45 Soxhlet apparatus and extracted continuously with ethanol. Removal of the ethanol by distillation in vacuo resulted in 5.7 g of a target compound with a purity of 98.9% (determined by gas chromatography). The melting point was 113 C. This corresponds to a yield of 92.3% of theory. The product was identified through a mixed melting point with an authentic sample.

References: [1]Patent: US6515139,2003,B1 .
[2]Patent: US2004/102505,2004,A1 .

13
[ 57707-21-8 ]
[ 54367-66-7 ]
[ 10234-66-9 ]

Yield	Reaction Conditions	Operation in experiment
92.5%	With sodium hydroxide;	EXAMPLE 15 Preparation of 1-methyl-2-pyrazolin-5-one, Workup by Liquid/Liquid Extraction 10 g of 5-chloro-1-methylpyrazole-4-carboxylic acid were reacted as in Example 1 initially with 100 g of 25% by weight sodium hydroxide solution and subsequently under acidic conditions. After the acidic reaction mixture had been neutralized to pH 6.5 with 25% by weight sodium hydroxide solution, the reaction mixture was transferred into a liquid/liquid extractor and extracted with isobutanol at the boiling point of the solvent. After isolation of the organic phase and removal of the isobutanol by distillation, 5.8 g of 1-methyl-2-pyrazolinone remained (GC purity: 98.1%). The melting point was 112 C. The yield was 92.5% of theory.

References: [1]Patent: US2004/102505,2004,A1 .

14
[ 351003-36-6 ]
[ 10234-66-9 ]
[ 1159186-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 110.0℃; for 2.0h;	A solution of 2-fluoro-5-iodobenzonitrile (100 mg, 0.405 mmol) and 2-methyl- 2,4-dihydro-3H-pyrazol-3-one (63.6 mg, 0.648 mmol) in 5 ml_ of 1 -methyls- pyrrol id inone was treated with cesium carbonate (396 mg, 1.22 mmol) and stirred at 110 0C for 2 hour. The reaction was diluted with 50 ml_ water and extracted with 2 x 5OmL ethyl acetate. The combined organic layers were washed with 50 ml_ water, 5OmL brine, dried over magnesium sulfate, filtered, and evaporated to afford crude material. Purification by normal phase chromatography provided the title compound as a white solid (93 mg). LC/MS 5-100% acetonithle/tfa-water/tfa (6 min gradient) 4.74 min [(M+H)+ = 326]. 1 H NMR (400 MHz, DMSO- c/6) delta ppm 8.33 (1 H, d, J=2.2 Hz), 8.04 (1 H, dd, J=8.9, 2.2 Hz), 7.45 (1 H, d, J=2.0 Hz), 6.95 (1 H, d, J=8.9 Hz), 5.99 (1 H, d, J=2.0 Hz), 3.67 (3 H, s)

References: [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 140.

15
[ 60-35-5 ]
[ 13636-88-9 ]
[ 10234-66-9 ]
[ 1169757-10-1 ]