103646-82-8|5-Amino-1-(p-tolyl)-1H-pyrazole-4-carbonitrile| Ambeed

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Quality Control of [ 103646-82-8 ] Purity: 97% SDS Specification

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Product Details of [ 103646-82-8 ]

CAS No. :	103646-82-8
Formula :	C₁₁H₁₀N₄
M.W :	198.22
SMILES Code :	CC1=CC=C(C=C1)N1N=CC(C#N)=C1N
MDL No. :	MFCD00052944
InChI Key :	MJQOLPWOOIMZDA-UHFFFAOYSA-N
Pubchem ID :	2800424

Safety of [ 103646-82-8 ]

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

Computational Chemistry of [ 103646-82-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.09
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	57.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.63 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.88
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	2.18
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.64
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.	1.19
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	1.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.92
Solubility	0.239 mg/ml ; 0.0012 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.23
Solubility	0.116 mg/ml ; 0.000584 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < 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	-3.05
Solubility	0.178 mg/ml ; 0.000899 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	Yes
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.	-5.96 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)	1.94

Application In Synthesis of [ 103646-82-8 ]

* 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 [ 103646-82-8 ]

[ 103646-82-8 ] Synthesis Path-Downstream 1~36

1
[ 103646-82-8 ]
[ 77287-34-4 ]
[ 103984-26-5 ]

References: [1]Journal of Organic Chemistry,1956,vol. 21,p. 1240,1242.

2
[ 103646-82-8 ]
[ 100061-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 18A 5-Amino-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide In analogy to the preparation of Example 16A, 1.02 g (47percent of theory) of the desired product are obtained from 2 g (10.1 mmol) of <strong>[103646-82-8]5-amino-1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile</strong> (Example 3A) in a mixture of 25 ml of ethanol, 20 ml of 30percent strength hydrogen peroxide and 40 ml of 25percent strength ammonia. LC-MS (Method 1): Rt=2.7 min. MS (ESI pos): m/z=217 (M+H)+.

References: [1]Journal of Organic Chemistry,1956,vol. 21,p. 1240,1242.
[2]Patent: US2007/161662,2007,A1 .

3
[ 123-06-8 ]
[ 539-44-6 ]
[ 103646-82-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; for 2h;Reflux;	General procedure: A mixture of the appropriate phenylhydrazine (0.001 mol)and 10 mL of ethanol was stirred and allowed to reflux.Then, 2-(ethoxymethylene)malononitrile (0.001 mol) dissolvedin 10 mL of ethanol was slowly added. The reactionmixture was refluxed for 2 h. The reaction mixture waspoured into 50 mL of ice-cold water. The precipitate wascollected by filtration and washed with water to provide10a-c in 61-80% yield.
80%	In ethanol; for 2h;Reflux;	General procedure: A mixture of the appropriate phenylhydrazine (0.001 mol) and10 mL of ethanol was stirred and allowed to reflux. Then, 2-(ethoxymethylene)malononitrile (0.001 mol) dissolved in 10 mL of ethanol was slowly added. The reaction mixture was refluxed for 2 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 7-12 in 48-90% yield.
	In ethanol; for 3h;Reflux;	General procedure: A stirred mixture of para-substituted phenylhydrazine hydrochloride (0.025 mol) was dissolved inH2O (30 mL), then the pH of the mixture was adjusted to pH 7-8 by the dropwise addition of 10% NaOHsolution to form the free para-substituted phenyl hydrazines, which were then refluxed for 3 h withethoxymethylene malononitrile in an ethanol medium. After completion of the reaction, the reactionmixture was allowed to cool at room temperature, and the solid 2a-2d were filtered under vacuum. Thecrude products obtained were recrystallized from DMF to afford the pure products.

References: [1]Medicinal Chemistry Research,2018,vol. 27,p. 1876 - 1884.
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3061 - 3069.
[3]Heterocyclic Communications,2005,vol. 11,p. 385 - 388.
[4]European Journal of Medicinal Chemistry,2008,vol. 43,p. 771 - 780.
[5]Journal of Organic Chemistry,1956,vol. 21,p. 1240,1242.
[6]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2121 - 2125.
[7]Zeitschrift fur Naturforschung, B: Chemical Sciences,2009,vol. 64,p. 840 - 846.
[8]Molecules,2015,vol. 20,p. 807 - 821.
[9]RSC Advances,2015,vol. 5,p. 55179 - 55185.
[10]RSC Advances,2016,vol. 6,p. 24491 - 24500.
[11]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1732 - 1737.

4
[ 64-18-6 ]
[ 103646-82-8 ]
[ 54738-75-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	for 12h;Reflux;	General procedure: A mixture of 5-amino-1-phenyl-1H-pyrazole-4-carbonitriles (7-12)(0.01 mol) and 20 mL of formic acid was stirred and allowed to reflux for 12 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 13-18 in 68-89% yield.

References: [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3061 - 3069.
[2]Archiv der Pharmazie,2014,vol. 347,p. 559 - 565.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2121 - 2125.
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1732 - 1737.

5
[ 103646-82-8 ]
5,5'-(diazene-1,2-diyl)bis(1-(3-bromo-4-methylphenyl)-1H-pyrazole-4-carbonitrile) [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 8819 - 8822.

6
[ 103646-82-8 ]
5,5'-(diazene-1,2-diyl)bis[1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile] [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 8819 - 8822.

7
[ 103646-82-8 ]
[ 23000-47-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2121 - 2125.
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1732 - 1737.
[3]Medicinal Chemistry Research,2018,vol. 27,p. 1876 - 1884.
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3061 - 3069.

8
[ 103646-82-8 ]
[ 650628-55-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2121 - 2125.

9
[ 103646-82-8 ]
N-pyridin-4-ylmethylene-N'-(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-hydrazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2121 - 2125.

11
[ 637-60-5 ]
[ 123-06-8 ]
[ 103646-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	EXAMPLE 3A 5-Amino-1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile In analogy to the preparation of Example 1A, 2.16 g (57percent of theory) of the desired product are obtained starting from 3 g (18.9 mmol) of 4-methylphenylhydrazine hydrochloride, 2.3 g (18.9 mmol) of ethoxymethylenemalononitrile and 7.9 ml (56.7 mmol) of triethylamine. LC-MS (Method 1): Rt=3.0 min. MS (ESI pos): m/z=199 (M+H)+.
		General procedure: A stirred mixture of para-substituted phenylhydrazinehydrochloride (0.025 mol) was dissolved in H2O (30 mL), thenthe pH of the mixture was adjusted to pH 7?8 by the dropwiseaddition of 10percent NaOH solution to form the free para-substitutedphenyl hydrazines, which were then refluxed for 3 h with ethoxymethylene malononitrile in an ethanol medium. After completionof the reaction, the reaction mixture was allowed to cool at room temperature, and the solid were filtered under vacuum. The crudeproducts obtained were recrystallized from anhydrous ethanol togive the light yellow solid.

References: [1]Patent: US2007/161662,2007,A1 .
[2]Chinese Chemical Letters,2017,vol. 28,p. 377 - 382.

12
[ 103646-82-8 ]
[ 122-51-0 ]
[ 103984-26-5 ]

References: [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 771 - 780.

13
[ 103646-82-8 ]
[ 108-94-1 ]
[ 1094618-80-0 ]

References: [1]Synthetic Communications,2008,vol. 38,p. 4369 - 4378.

14
[ 103646-82-8 ]
[ 1150312-12-1 ]

References: [1]Synthetic Communications,2009,vol. 39,p. 1186 - 1195.

15
[ 103646-82-8 ]
[ 108-94-1 ]
C₁₇H₁₈N₄ [ No CAS ]

References: [1]Journal of Chemical Research,2009,p. 562 - 564.

16
[ 103646-82-8 ]
[ 120-92-3 ]
C₁₆H₁₆N₄ [ No CAS ]

References: [1]Journal of Chemical Research,2009,p. 562 - 564.

17
[ 103646-82-8 ]
[ 372-09-8 ]
[ 1203570-55-1 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2009,vol. 64,p. 840 - 846.

18
[ 103646-82-8 ]
[ 141-97-9 ]
[ 1269662-42-1 ]

References: [1]Molecules,2011,vol. 16,p. 1878 - 1887.

19
[ 103646-82-8 ]
[ 105-45-3 ]
[ 1269662-35-2 ]