10250-59-6|Methyl 1,3-dimethyl-1H-pyrazole-5-carboxylate| Ambeed

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Quality Control of [ 10250-59-6 ] Purity: 95% SDS Specification

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Product Details of [ 10250-59-6 ]

CAS No. :	10250-59-6
Formula :	C₇H₁₀N₂O₂
M.W :	154.17
SMILES Code :	O=C(C1=CC(C)=NN1C)OC
MDL No. :	MFCD06204177
InChI Key :	KYQGPXFQWUSRMY-UHFFFAOYSA-N
Pubchem ID :	12218441

Safety of [ 10250-59-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 10250-59-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.43
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	39.73
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	44.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.94
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	0.82
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.52
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.	0.33
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	0.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.52
Solubility	4.69 mg/ml ; 0.0304 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.	-1.33
Solubility	7.23 mg/ml ; 0.0469 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	-1.25
Solubility	8.77 mg/ml ; 0.0569 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.	-6.66 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)	1.82

Application In Synthesis of [ 10250-59-6 ]

* 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 [ 10250-59-6 ]

[ 10250-59-6 ] Synthesis Path-Downstream 1~17

1
[ 10250-59-6 ]
[ 5744-56-9 ]

Yield	Reaction Conditions	Operation in experiment
81%		c. Synthesis of 1 ,3-dimethyl-pyrazole-5-carboxylic acid; 3,delta-dimethyl-pyrazole-delta-carboxylic acid methylester (5.14 Kg) is added to an aqueous solution of 20% sodium hydroxide (10 L) at O0C. The reaction mixture is stirred at room temperature for 18 hours and cooled to O0C. Concentrated hydrochloric acid (4.2 L) is then added to the reaction mixture in over 7 hours. The resulting thick slurry is stirred at room temperature for 18 hours. The mixture is filtered, and the solids are washed with water (500 mL), and dried in a vacuum oven for 18 hours (700C and 26 mm Hg) to provide 3.8 Kg of 1 ,3- dimethyl-pyrazole-delta-carboxylic acid (81 % yield with a purity of >97 % by HPLC).

References: [1]Patent: WO2006/48761,2006,A2 .Location in patent: Page/Page column 33.
[2]Gazzetta Chimica Italiana,1956,vol. 86,p. 797,808.

2
[ 4027-57-0 ]
[ 74-88-4 ]
[ 10250-61-0 ]
[ 10250-59-6 ]

References: [1]Gazzetta Chimica Italiana,1956,vol. 86,p. 797,808.

4
[ 25016-17-5 ]
[ 77-78-1 ]
[ 10250-59-6 ]

Yield	Reaction Conditions	Operation in experiment
69%		b. Synthesis of I.S-dimethyl-pyrazole-delta-carboxylic acid methylester; S-methyl-pyrazole-delta-carboxylic acid methyl ester (6.8 Kg Kg) is dissolved in DMF (8L) and dimethyl sulfate (6.0 L) is added dropwise in over three hours. The reaction is exothermic and the addition of dimethyl sulfate must be controlled so that the internal temperature does not exceed 900C. After complete addition, the mixture is heated for 18 hours at 800C. The mixture is then cooled to room temperature, diluted with ice (3.4 Kg), and cooled in an ice bath. A solution of aqueous 28% ammonium hydroxide (8.6 L) is added to the reaction mixture over 3 hours. The resulting mixture is stirred for 18 hours, diluted with ethyl acetate (12 L) and water (16 L), extracted, and the layers are separated. The organic layer is washed with water (4L), dried over MgSO4, filtered, and concentrated under reduced pressure to provide 5.14 Kg of 1 ,3-dimethyl-pyrazole-delta-carboxylic acid methylester (69 % yield with a purity of >90 % by HPLC). The crude product is used directly in the next step.

References: [1]Patent: WO2006/48761,2006,A2 .Location in patent: Page/Page column 33.
[2]Journal of Agricultural and Food Chemistry,2016,vol. 64,p. 9586 - 9591.

Yield	Reaction Conditions	Operation in experiment
		Example 14 alpha-Cyano-p-fluoro-3-(1,5-dimethyl-3-pyrazolyl)-beta-oxopropionanilide A solution of 2.6 g of beta-(1,5-dimethyl-3-pyrazolyl)-beta-oxopropionitrile and 1.8 g of triethylamine in 20 ml of dimethoxyethane is treated with 2.4 g of p -fluorophenylisocyanate. After standing overnight the crystalline, crude mixture is treated with dilute HCl and the product collected, washed with water, dried, and triturated with methanol and ethyl acetate to give colorless crystals, m.p. 235-240. After recrystallization from ethyl acetate, the compound melts at 239-241. The starting material is prepared as follows: 58 g of acetone and 146 g of ethyl oxalate are condensed with a solution of 26 g of sodium in 500 ml of reagent methanol. The obtained sodium salt of methyl 2,4-dioxovalerate is washed with ethanol and dried, m.p. 260-1 (dec.). Following the method of v. Auwers and Hollmann, Ber. 59 , 605, 1282 (1926), an aqueous solution (100 ml) of 20 g of the sodium salt of methyl 2,4-dioxovalerate is treated with a solution of 6.4 ml of methylhydrazine in aqueous sulfuric acid prepared from 12.5 g of cold conc. H2SO4 and 20 g of ice. After stirring for 1 hr, the solution is carefully made alkaline with sodium hydroxide solution. The products are extracted with diethyl ether, and the etheral solution dried with sodium sulfate and evaporated. On trituration with cold diethyl ether, crystals of methyl 1,5-dimethyl-3-pyrazolylcarboxylate, m.p. 72-5, are obtained. Recrystallization from diethyl ether raises the m.p. to 75-7. The etheral filtrate from the trituration is evaporated, and the residual oil distilled in vacuo , affording methyl 1,3-dimethyl-5-pyrazolylcarboxylate , b.p. 100-102/12 mbar.

6
[ 10250-59-6 ]
[ 57012-20-1 ]