852443-61-9|3-(Trifluoromethyl)-1H-pyrazol-5-amine| Ambeed

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Quality Control of [ 852443-61-9 ] Purity: 97% SDS Specification

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Product Details of [ 852443-61-9 ]

CAS No. :	852443-61-9
Formula :	C₄H₄F₃N₃
M.W :	151.09
SMILES Code :	NC1=CC(=NN1)C(F)(F)F
MDL No. :	MFCD06738292
InChI Key :	WVORIWCOSAWJJE-UHFFFAOYSA-N
Pubchem ID :	19623305

Safety of [ 852443-61-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 852443-61-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	27.99
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.	0.48
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	0.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.17
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.	0.6
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	1.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.09

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.58
Solubility	3.99 mg/ml ; 0.0264 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.	-1.52
Solubility	4.57 mg/ml ; 0.0302 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	-1.75
Solubility	2.72 mg/ml ; 0.018 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	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)	1.59

Application In Synthesis of [ 852443-61-9 ]

* 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 [ 852443-61-9 ]

[ 852443-61-9 ] Synthesis Path-Downstream 1~33

1
[ 110234-68-9 ]
[ 852443-61-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With hydrogenchloride; hydrazine hydrochloride; In water; for 2h;Reflux;	The obtained trifluoroacetoacetonitrile (27.4 g, 200 mmol) was mixed with water (200 ml), and hydrazine monohydrochloride (15.1 g, 220 mmol) and 35% concentrated hydrochloric acid (41.7 g, 400 mmol) were sequentially added thereto And the mixture was stirred under heating reflux for 2 hours. After standing to cool, potassium carbonate was added to the reaction mixture to make it basic, followed by extraction three times with ethyl acetate (100 ml). The organic layers were combined, washed with saturated brine (100 ml), and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the desired product (13.5 g, yield: 45%).
16%	With hydrazine; In ethanol; for 5h;Heating / reflux;	A solution of 4, 4, 4-trifluoro-3-oxo-butyronitrile (Method 23; 11.0 g, 0. 080 mol) and hydrazine monohydrate (3.89 ml, 0. 080 mol) inEtOH (400 ml) was heated at reflux for 5 hours. After cooling to25'C, the solvent was removed under reduced pressure. The resulted residue was dissolved in DCM (500 ml), washed with brine (2 x 200ml), and dried overNa2S04. After evaporation of the solvent, the resulted residue was purified by column chromatography (hexane: EtOAc = 1 : 1) to give the title compound as a pale yellow solid (1.93 g, 16%). 1H NMR (400 MHz) : 8 5.35 (s, 2 H), 5.56 (s,1 H), 12.10 (br s,1 H).
2%	With hydrazine; In ethanol; for 8h;Heating / reflux;	Step B. A mixture of the title compound from Step A above (12.5 g) and hydrazine monohydrate (6.0 g) in absolute EtOH (300 mL) was heated to reflux under a nitrogen atmosphere for 8 h, cooled to room temperature and concentrated. The remaining oil was taken up in CH2Cl2 (150 mL), washed with saturated aqueous NaCl, dried (MgSO4), filtered, concentrated and purified by chromatography (silica, CH2Cl2/Me0H) to give the title compound (0.25 g, 2%). [MH]+ = 152.

References: [1]Patent: JP2017/141196,2017,A .Location in patent: Paragraph 0072-0074.
[2]Patent: WO2005/49033,2005,A1 .Location in patent: Page/Page column 97.
[3]Patent: WO2008/63671,2008,A2 .Location in patent: Page/Page column 133-134.
[4]Journal of Medicinal Chemistry,2017,vol. 60,p. 5099 - 5119.

3
[ 852443-61-9 ]
[ 20577-61-1 ]
[ 916211-81-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	In methanol; at 120℃; for 0.2h;Sealed vial; Irradiation;	Step C. Using a microwave, a mixture of the title compound from Step B above (150 mg) and commercially available methyl acetopyruvate (150 mg) in MeOH (1 mL) in a sealed vial was heated at 120C for 12 min, concentrated and purified by chromatography (silica, CH2Cl2) to give 7-methyl-2-trifluoromethyl- pyrazolo[l,5-a]pyrimidine-5-carboxylic acid methyl ester (0.15 g, 58%). [MH]+ = 260.

References: [1]Patent: WO2008/63671,2008,A2 .Location in patent: Page/Page column 134.

4
[ 128648-60-2 ]
[ 852443-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrochloride; triethylamine; In ethanol; for 16h;Reflux;	To a solution of (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en--2-one, (Compound [XXIV) (7.0Og, 38.2 mmol, 1.0 eq.) in ethanol (150 mL) in a 250 mL round bottom flask was added hydrazine hydrochloride (2.75 g, 40.16 mmol, 1.05 eq.) followed by triethylamine (4.05g, 40.16 mmol, 1.05 eq.). The reaction mixture was heated to reflux for 16 hours. After cooling and concentration, the residue was purified by silica gel chromatography using CHCl3- MeOH(10%) as the eluant to give Compound [XXV]: LCMS m/e 152 (M+H); 1H NMR (400 MHz, DMSO-d6) delta ppm 5.32 (s, 2 H) 5.51 (s, 1 H) 12.12 (br. s, 1 H)

References: [1]Patent: WO2010/104933,2010,A1 .Location in patent: Page/Page column 136.

5
[ 852443-61-9 ]
sodium (1,3-dioxopropan-2-ylidyne)azinate monohydrate [ No CAS ]
C₇H₃F₃N₄O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1165 - 1168.

6
[ 27421-51-8 ]
[ 852443-61-9 ]
[ 1694-31-1 ]
[ 1369959-35-2 ]