114474-28-1|4-(1H-Pyrazol-4-yl)aniline| Ambeed

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Quality Control of [ 114474-28-1 ] Purity: 97% SDS Specification

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Product Details of [ 114474-28-1 ]

CAS No. :	114474-28-1
Formula :	C₉H₉N₃
M.W :	159.19
SMILES Code :	NC1=CC=C(C2=CNN=C2)C=C1
MDL No. :	MFCD11932600
InChI Key :	NIIAGRDJQKKSKU-UHFFFAOYSA-N
Pubchem ID :	13977013

Safety of [ 114474-28-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 114474-28-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	48.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.84
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	1.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.67
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.	0.85
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	1.86
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.28

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.17
Solubility	1.08 mg/ml ; 0.00676 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.	-1.9
Solubility	1.99 mg/ml ; 0.0125 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	-3.38
Solubility	0.0662 mg/ml ; 0.000416 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.	-6.45 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	1.0 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)	1.39

Application In Synthesis of [ 114474-28-1 ]

* 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 [ 114474-28-1 ]

[ 114474-28-1 ] Synthesis Path-Downstream 1~35

1
[ 114474-26-9 ]
[ 114474-28-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With palladium 10% on activated carbon; hydrogen; at 20.0℃;	To a suspension of 4-(4-Nitrophenyl)-1H-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2:1 v/v) was added 10% Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with H2 from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tlc showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with H2 as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94%) of a yellow solid. ?H NIVIR (400 MHz, DMSO-d6) oe 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+.
94%	With palladium 10% on activated carbon; hydrogen; In methanol; 1,2-dimethoxyethane; at 20.0℃; under 1838.94 Torr; for 2.0h;	[0092] To a suspension of 4-(4-Nitrophenyl)-lH-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2: 1 v/v) was added 10% Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tic showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94%) of a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+.
	With hydrogen;	Intermediate 259 corresponds with CAS: 114474-26-9. Hydrogenation of the nitro group according to wellk-known methods afforded intermediate 260.

90 mg

With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; for 4.0h;

A mixture containing 4-(4-nitrophenyl)-1H-pyrazole (commercially available from Combi-Blocks, 110 mg), 10% Pd/C (11 mg)and methanol (5 mL) was stirred at room temperature for 4 hours under a hydrogen atmosphere. Insoluble substances in the reaction mixture were filtered off. Then, the filtrate was concentrated under a reduced pressure, and thereby 4-(1H-pyrazol-4-yl)aniline (90 mg)as a brown solid was obtained.

References: [1]Patent: WO2016/210331,2016,A1 .Location in patent: Paragraph 0087; 0088.
[2]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0091-0092.
[3]CrystEngComm,2019,vol. 21,p. 2818 - 2831.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619.
[5]Patent: WO2019/120209,2019,A1 .Location in patent: Page/Page column 216.
[6]Patent: US2019/337926,2019,A1 .Location in patent: Paragraph 0692.

2
[ 114474-28-1 ]
[ 81-16-3 ]
[ 114474-30-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619.

3
[ 104-03-0 ]
PbO [ No CAS ]
[ 114474-28-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619.

4
[ 93072-94-7 ]
[ 114474-28-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619.

5
[ 114474-28-1 ]
[ 114474-32-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619.

6
[ 1643545-71-4 ]
[ 114474-28-1 ]
[ 1181326-94-2 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3856 - 3873.

7
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-5,7-dihydrofuro[3,4-d]pyrimidin-2-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

References: [1]Patent: WO2016/210331,2016,A1 .
[2]Patent: WO2016/210330,2016,A1 .

8
[ 114474-28-1 ]
C₂₆H₂₄N₆O₃ [ No CAS ]