51516-70-2|5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile| Ambeed

Structure of 51516-70-2

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Quality Control of [ 51516-70-2 ] Purity: 97% SDS Specification

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Product Details of [ 51516-70-2 ]

CAS No. :	51516-70-2
Formula :	C₁₀H₇FN₄
M.W :	202.19
SMILES Code :	N#CC1=C(N)N(C2=CC=C(F)C=C2)N=C1
MDL No. :	MFCD00102729
InChI Key :	SZEJYPAPBGNEMH-UHFFFAOYSA-N
Pubchem ID :	688685

Safety of [ 51516-70-2 ]

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

Computational Chemistry of [ 51516-70-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	52.64
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.	1.73
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	1.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.89
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.	1.31
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	1.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.77
Solubility	0.341 mg/ml ; 0.00168 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.	-2.95
Solubility	0.225 mg/ml ; 0.00111 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	-2.94
Solubility	0.233 mg/ml ; 0.00115 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.	-6.18 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	0.0
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)	1.95

Application In Synthesis of [ 51516-70-2 ]

* 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 [ 51516-70-2 ]

[ 51516-70-2 ] Synthesis Path-Downstream 1~41

1
[ 122-04-3 ]
[ 51516-70-2 ]
N-[4-Cyano-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-4-nitro-benzamide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 858 - 861.

2
[ 371-14-2 ]
[ 123-06-8 ]
[ 51516-70-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	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.5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (10a)Yield: 61%. MP: 173-174 C. IR (cm-1): 3297-3183; 2225;1662; 1568; 1222. 1H NMR (400 MHz, DMSO-d6, TMS, deltain p.p.m.): 7.31-7.25; (m; 2 H; H3?, H5?); 7.54-7.49; (m;2H; H2?, H6?); 7.67; (s; 1 H; H3). 13C NMR (100 MHz,DMSO-d6, TMS, delta in ppm): 73.2 (C4); 114.8 (CN); 116.3(d; J = 22.8 Hz; C3?, C5?); 126.9 (d; J = 8.9 Hz; C2?, C6?);133.7 (d; J = 2.8 Hz; C1?) 141.7 (C5); 151.4 (C3); 161.2 (d;J = 243.6 Hz; C4?). 19F NMR (376 MHz, DMSO-d6, TMS, deltain p.p.m.): -114.26. EI [M + 1]+ 203.07.
61%	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]European Journal of Organic Chemistry,2018,vol. 2018,p. 1514 - 1524.
[2]Tetrahedron Letters,2008,vol. 49,p. 305 - 310.
[3]Medicinal Chemistry Research,2018,vol. 27,p. 1876 - 1884.
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3061 - 3069.
[5]Journal of Medicinal Chemistry,1991,vol. 34,p. 2892 - 2898.
[6]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2758 - 2761.
[7]Chemical Biology and Drug Design,2014,vol. 83,p. 272 - 277.
[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.
[12]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 2644 - 2649.
[13]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 87 - 96.

3
[ 371-14-2 ]
[ 122-51-0 ]
[ 109-77-3 ]
[ 51516-70-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2892 - 2898.

4
[ 624-83-9 ]
[ 51516-70-2 ]
[ 135108-59-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2892 - 2898.

6
[ 51516-70-2 ]
C₂₀H₁₄N₈F₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2758 - 2761.

7
[ 371-40-4 ]
[ 51516-70-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2892 - 2898.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2892 - 2898.

8
[ 823-85-8 ]
[ 123-06-8 ]
[ 51516-70-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium ethanolate; sodium hydride; In ethanol; at 20℃; for 2h;Heating / reflux;	Sodium hydride as a 60% dispersion in mineral oil (5.90 g, 1.2 eq, 0.147 mol.) was added slowly to ethanol (200 ml) at room temperature. To the solution of sodium ethoxide in ethanol was added 4-fluorophenylhydrazine hydrochloride (23.96 g, 1.2 eq, 0.147 mol.), addition of ethoxymethylene malonitrile (15.00 g, 1.0 eq, 0.123 mol.) shortly followed. The reaction mixture was heated to reflux with stirring for 2 hours. The reaction was then allowed to cool to room temperature, once at room temperature diethyl ether (50 ml) was added to the reaction mixture. The resultant precipitate was collected by filtration, washed with diethyl ether (2 x 100 ml) and dried in vacuo to give the title compound as a beige solid (21.5 g, 0.106 mol, 86%). LCMS: [M+H]+=203, Rt = 1.02 min, 100% purity.
46%	With triethylamine; In ethanol; at 50℃; for 2h;	Example 5A8.7 g (53.5 mmol) of 4-fluorphenylhydrazine hydrochloride was suspended with 6.5 g (53.5 mmol) of ethoxymethylenemalononithle in 13 ml of ethanol, and 22.2 ml (160 mmol) of thethylamine were added. The reaction mixture was heated to 500C for 2 h. After cooling to room temperature the solvent was removed under reduced pressure. The remaining residue was treated with water (25 ml) and extracted three times with ethyl acetate. The organic layer was dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. The remaining residue was <n="60"/>purified by preparative MPLC (SiO2, eluent CH2CI2). 5.0 g (46% of theory) of the product were obtained as an oil, that solidifies over night.LC-MS (Method 1 ): RT = 1.06 minMS (ESI pos): m/z = 203 (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 10% 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]European Journal of Organic Chemistry,2008,p. 3377 - 3381.
[2]Patent: EP1746099,2007,A1 .Location in patent: Page/Page column 14.
[3]Patent: WO2009/68617,2009,A1 .Location in patent: Page/Page column 58-59.
[4]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1425 - 1428.
[5]Chinese Chemical Letters,2017,vol. 28,p. 377 - 382.
[6]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 1825 - 1830.
[7]European Journal of Medicinal Chemistry,2019,vol. 182.

9
[ 77287-34-4 ]
[ 51516-70-2 ]
1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	at 180℃; for 3h;	Title compound 1A, <strong>[51516-70-2]5-amino-1-(4-fluoro-phenyl)-1H-pyrazole-4-carbonitrile</strong> (21.5 g, 0.106 mol) was suspended in formamide (200 ml). The suspension was heated to 180C for 3 hours and then allowed to cool to room temperature. To the reaction mixture was then added water (100 ml) and the resultant precipitate was collected by filtration, washed with water (2 x 100 ml), isopropyl alcohol (100 ml) and diethyl ether (100 ml), then dried on the filter to give the title compound as a beige solid (11.5 g, 55 mmol, 47%). This was then recrystalised from methanol to yield the title compound as an off-white solid (8.2 g, 35.8 mmol, 34%). LCMS: [M+H]+= 230, Rt = 1.09 min, 100% purity.

References: [1]Patent: EP1746099,2007,A1 .Location in patent: Page/Page column 14.

10
[ 75-05-8 ]
[ 51516-70-2 ]
[ 936758-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol; at 200℃; for 45h;Product distribution / selectivity;	Method B5-Amino-1-(4-fluorophenyl)-1/-/-pyra2thetale-4-carbonitrile (which may be prepared as described in J. Med. Chem., 1991 , 34, 2892-2898) (7.45g, 37mmol) and acetonitrile (56ml, 1.07mol) in 2M ammonia / methanol (150ml) were stirred and heated to 200C in a steel pressure vessel for 45 hours. The reaction mixture was cooled and the precipitate was filtered, washed with methanol and dissolved in ethyl acetate. The ethyl acetate solution was filtered in order to remove a small amount of insoluble solid and then concentrated in vacuo until appearance of precipitate. The ethyl acetate suspension was diluted with an equal volume of chloroform and the solid filtered and washed with 1 :1 chloroform / 40:60 petroleum ether to give the title compound (4.37g). LCMS: tRET = 2.42 min; MH+ = 244 A further 1.3g of title compound was obtained from the acetonitrile / 2M ammonia in methanol mother liquor using a similar work-up.

References: [1]Patent: WO2007/54294,2007,A1 .Location in patent: Page/Page column 34.

11
[ 51516-70-2 ]
[ 51516-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 0 - 25℃; for 2h;	5-Amino-i -(4-fluorophenyl)-i H-pyrazole-4-car- boxamide (Step 1, 900 mg, 4.45 mmol) was added dropwise to sulfuric acid (10 mE) at 0 C. The resulting solution was stirred for 2 hat 25 C. The pH of the solution was adjusted to 8 by the addition of sodium carbonate (10% aqueous). The resulting mixture was extracted with dichloromethane (4x50 mE) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to provide 5-amino-i -(4-fluorophenyl)- 1H-pyrazole-4-car- boxamide which was used in Step 3 without further purification. ECMS: (ESI) mlz 221 [M+H].

References: [1]Tetrahedron Letters,2008,vol. 49,p. 305 - 310.
[2]Patent: US2016/185785,2016,A1 .Location in patent: Paragraph 2046; 2048.

12
[ 51516-70-2 ]
[ 1015862-36-8 ]
[ 1050619-83-4 ]
[ 1050619-72-1 ]

References: [1]European Journal of Organic Chemistry,2008,p. 3377 - 3381.

13
[ 51516-70-2 ]
[ 1431459-41-4 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1425 - 1428.

14
[ 51516-70-2 ]
[ 1015862-36-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With isopentyl nitrite; In tetrahydrofuran; at 120℃; under 5250.53 Torr; for 0.333333h;	General procedure: A solution of the selected heterocyclic starting material (1.00 mmol) in THF (10 mL) and a solutionof isopentyl nitrite (141 mg, 1.20 mmol) in THF (10 mL) were both pumped at a flow rate of 0.25 mLmin1 with a Vapourtech ?Easy MedChem V3? system, meeting at a PTFE T-piece and the outputflowing through a 10.0 mL coil reactor maintained at 120 C, giving a residence time of 20 min.The pressure of the system was maintained at 7 bar with a back-pressure regulator. For compoundswhere an isolated yield was reported: the output mixture was concentrated under reduced pressureto give an oil (or powder). The oil (or powder) was purified using column chromatography withvarious mixtures of ethyl acetate and hexane as the eluent, or by recrystallisation using methanol, togive isolated compounds that showed no impurities by NMR spectroscopy. For compounds where aconversion was reported (due to volatility of products), the output mixture was carefully concentratedunder a reduced pressure of 100 mbar for 10 min and the conversion was calculated by integration ofproduct peaks to a quantified internal standard (nitrobenzene).

References: [1]Molecules,2019,vol. 24.
[2]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1425 - 1428.

15
[ 51516-70-2 ]
[ 1456790-22-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 130 - 140℃;	General procedure: A mixture of <strong>[51516-70-2]5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile</strong> 1a (0.002mol), sodium azide (0.004 mol) and ammonium chloride (0.004mol) in DMF (15 mL) was stirred at 130-140C for 16-18hand poured into cold water. The solid formed was filtered and recrystallizedfrom ethanol/water. The reactions were accompanied by means of TLC using silicagel 60 F254 plate and hexane/ethyl acetate (1:1) as eluent.Compounds 2b and 2c were prepared similarly. 2a(R=4-F): Yield: 62%; mp:172-173oC; IR (cm-1): 3413, 3355, 3321, 3108, 3006, 2920,2798, 2742, 1616, 1511, 1226, 1158, 941, 838; 1H NMR (500MHz, DMSO-d6)d: 6.43 (br, NH/NH2), 7.51 (2H, t,9.0Hz, H-Ar), 7.75 (2H, dd, 9.0. 4.8Hz, H-Ar), 8.01 (1H, s, H3-pyrazole);13C NMR (75MHz, DMSO-d6)d: 88.0, 116.3 (d, 22.5Hz), 126.3, 136.2, 138.1,146.8, 149.6, 159.8 (d, 245.4Hz); HR-MS: (C10H8FN7)calcd [M+H]+ 246.0880; found 246.0894.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 5748 - 5750.
[2]Chemical Biology and Drug Design,2014,vol. 83,p. 272 - 277.

16
[ 1140-38-1 ]
[ 51516-70-2 ]
5-chloro-N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

References: [1]Molecules,2015,vol. 20,p. 807 - 821.

17
C₁₁H₈Cl₂N₂O₂ [ No CAS ]
[ 51516-70-2 ]
5-chloro-1-(4-chlorophenyl)-N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-methyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

References: [1]Molecules,2015,vol. 20,p. 807 - 821.

18
C₁₂H₁₁ClN₂O₂ [ No CAS ]
[ 51516-70-2 ]
5-chloro-N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-methyl-1-(p-tolyl)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

References: [1]Molecules,2015,vol. 20,p. 807 - 821.

19
C₁₁H₈ClFN₂O₂ [ No CAS ]
[ 51516-70-2 ]
5-chloro-N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

References: [1]Molecules,2015,vol. 20,p. 807 - 821.

20
[ 77169-12-1 ]
[ 51516-70-2 ]
N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole-4-carboxamide [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 55179 - 55185.

21
1-(4-chlorophenyl)-3-phenyl-1H-pyrazole-4-carboxylic acid [ No CAS ]
[ 51516-70-2 ]
1-(4-chlorophenyl)-N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-phenyl-1H-pyrazole-4-carboxamide [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 55179 - 55185.

22
3-phenyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxylic acid [ No CAS ]
[ 51516-70-2 ]
N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-phenyl-1-(p-tolyl)-1H-pyrazole-4-carboxamide [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 55179 - 55185.

23
C₁₆H₁₁FN₂O₂ [ No CAS ]
[ 51516-70-2 ]
N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)-3-phenyl-1H-pyrazole-4-carboxamide [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 55179 - 55185.

24
[ 122-51-0 ]
[ 51516-70-2 ]
C₁₃H₁₁FN₄O [ No CAS ]

References: [1]RSC Advances,2016,vol. 6,p. 24491 - 24500.

25
[ 51516-70-2 ]
C₁₂H₁₀FN₇O [ No CAS ]

References: [1]RSC Advances,2016,vol. 6,p. 24491 - 24500.

26
[ 672-81-1 ]
[ 823-85-8 ]
[ 51516-70-2 ]