4498-72-0|1-(1H-Indazol-3-yl)ethanone| Ambeed

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Quality Control of [ 4498-72-0 ] Purity: 97% SDS Specification

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Product Details of [ 4498-72-0 ]

CAS No. :	4498-72-0
Formula :	C₉H₈N₂O
M.W :	160.17
SMILES Code :	CC(C1=NNC2=C1C=CC=C2)=O
MDL No. :	MFCD08234921
InChI Key :	BJEQUPDOOXOTLG-UHFFFAOYSA-N
Pubchem ID :	15684169

Safety of [ 4498-72-0 ]

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

Computational Chemistry of [ 4498-72-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.11
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	46.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.75 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.55
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	1.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	0.81
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	2.32
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.	-2.31
Solubility	0.782 mg/ml ; 0.00488 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.	-2.14
Solubility	1.16 mg/ml ; 0.00723 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	-3.23
Solubility	0.0932 mg/ml ; 0.000582 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.	-6.16 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)	1.43

Application In Synthesis of [ 4498-72-0 ]

* 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 [ 4498-72-0 ]

[ 4498-72-0 ] Synthesis Path-Downstream 1~35

1
[ 917-64-6 ]
[ 50264-88-5 ]
[ 4498-72-0 ]

References: [1]Chemische Berichte,1924,vol. 57,p. 1717.

2
[ 108-24-7 ]
[ 4498-72-0 ]
1,1'-(1H-indazole-1,3-diyl)diethanone [ No CAS ]

References: [1]Chemische Berichte,1924,vol. 57,p. 1717.

3
[ 4498-72-0 ]
[ 98952-79-5 ]

References: [1]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1959,vol. <8> 27,p. 123,124.

4
[ 40598-94-5 ]
[ 75-36-5 ]
[ 4498-72-0 ]

References: [1]Synthesis,1992,p. 937 - 939.

6
[ 90563-52-3 ]
isoamyl nitrite [ No CAS ]
[ 3484-07-9 ]
[ 4498-72-0 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 4115 - 4119.

7
[ 351457-12-0 ]
[ 75-16-1 ]
[ 4498-72-0 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	In tetrahydrofuran; at 0 - 20℃; for 12h;	To a solution of N-methoxy-N-methyl- 1 H-indazole-3 -carboxamide (950mg, 4.63mmol, 1 .Oeq.) in dry THF, the mixture was cooled down to 0°C. Methylmagnesium bromide (7.7m1, 23.l7mmol, 5.Oeq.) was added dropwise to the mixture at 0°C. The resulting mixture was stirred at r.t. for 12 h. Sat. NH4C1 solution (5m1) was added to the mixture. The solvent of the mixture was removed under vacuum, and the resulting residue was purified by column chromatography EAJPE = 1/2) to provide 1-(1H-indazol-3- yl)ethanone (610 mg, 82.3 percent yield) as yellow solid.
44%	In tetrahydrofuran; diethyl ether; at 0 - 23℃; for 18h;	To a stirred solution of compound C (700 mg, 3.4 mmol, 1 eq) in dry THF (40 mL) was added methyl magnesium bromide (1 M in diethyl ether, 11 mL, 10.2 mmol, , 3 eq) drop wise at 0 °C and the resulting mixture was stirred for 18 h at 23 °C. The reaction mixture was quenched with saturated aq. NH4CI solution and the organic components were extracted with ethyl acetate (100 ml). Ethyl acetate layer was concentrated in vacuo and the crude material was purified by flash chromatography (Combiflash) using 100-200 mesh silica gel eluting with 40percent ethyl acetate/ hexane to obtain the compound D (250 mg, 44percent) as colorless sticky material. (0287) [0277] FontWeight="Bold" FontSize="10" H NMR (400 MHz, OMSO-d6) delta 13.82 (s, 1 H), 8.17 (d, / = 8 Hz, 1 H), 7.66 (d, J = 8 Hz, 1 H), 7.47-7.43 (m, 1 H), 7.31 (t, J = 8 Hz, 1 H), 2.63 (s, 3 H); (0288) [0278] LCMS: m z = 161.1 [M+H], RT = 2.94 minutes; (Program Rl, Column W).
		7.3 1-(1H-Indazol-3-yl)ethanoneIn a round-bottomed flask, 2.4 g of <strong>[351457-12-0]N-methoxy-N-methyl-1H-indazole-3-carboxamide</strong> are placed in 140 ml of tetrahydrofuran at 0° C. and under argon. 19 ml of methylmagnesium bromide (3M in ethyl ether) are added dropwise. The mixture is stirred for one hour at 0° C. and 20 h at ambient temperature. It is cooled to 0° C. and 80 ml of water and 40 ml of a saturated solution of ammonium chloride are added. The mixture is extracted with 40 ml of ethyl acetate. The organic phase is washed with 40 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 1.6 g of compound are obtained.1H NMR (DMSO-d6, delta in ppm): 2.65 (s, 3H); 7.35 (m, 1H); 7.55 (m, 1H); 7.7 (d, 1H); 8.2 (d, 1H); 13.9 (s, 1H). M+H=161.

0.32 g

In tetrahydrofuran; at -78 - 20℃; for 7h;

Following a prenominal variation in the reported procedure refPreviewPlaceHolder[26], isobutyl chloroformate (0.79 g, 5.88 mmol) and N-methylmorpholine (0.59 g, 5.88 mmol) were added to a solution of 1H-indazole-3-carboxylic acid (0.6 g, 3.70 mmol) in anhydrous THF (15 mL) under nitrogen atmosphere at -20 °C, and the mixture was stirred for 4 h. To this mixture was added N,O-dimethylhydroxylamine hydrochloride (0.54 g, 5.55 mmol) suspended in 5 mL triethylamine. The reaction was then stirred at room temperature for 6 h, concentrated under vacuum and suspended in 20 mL n-hexane. The white precipitates (Winreb amide) formed were filtered off, dried and immediately transferred to a three neck flask containing 10 mL anhydrous THF cooled to -78 °C. To this was added methyl magnesium bromide (12percent in THF) (19 mL, 18.5 mmol). The reaction was allowed to stir at -78 °C for 2 h and then at room temperature for 5 h. The completion of the reaction was monitored by TLC. The reaction was quenched by slow addition of saturated aqueous solution of ammonium chloride followed by extraction with ethyl acetate (3 .x. 20 mL). The combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The resulting viscous mass was purified by column chromatography using hexane: ethyl acetate (85:15) solvent system to obtain desired acetyl derivative (0.32 g, 55percent); m.p. 182-185 °C (Lit. m.p. 184-186 °C) refPreviewPlaceHolder[26]; Rf = 0.71 (n-hexane:EtOAc 70:30); 1H NMR (400 MHz; CDCl3; TMS) delta 13.85 (s, 1H), 8.18 (d, J = 7.2 Hz, 1H), 7.67 (d, J = 7.2 Hz, 1H), 7.46 (t, J = 7.3 Hz, 1H), 7.32 (t, J = 7.3 Hz, 1H), 2.65 (s, 3H).

References: [1]Tetrahedron,2007,vol. 63,p. 419 - 428.
[2]Patent: WO2018/15818,2018,A2 .Location in patent: Paragraph 00237.
[3]Patent: WO2018/64135,2018,A1 .Location in patent: Paragraph 0275-0278.
[4]Patent: US2011/65700,2011,A1 .Location in patent: Page/Page column 17.
[5]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5138 - 5145.

8
[ 887577-66-4 ]
[ 4498-72-0 ]

References: [1]Tetrahedron,2007,vol. 63,p. 419 - 428.

9
[ 4498-67-3 ]
[ 4498-72-0 ]

References: [1]Tetrahedron,2007,vol. 63,p. 419 - 428.
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5138 - 5145.
[3]Patent: WO2018/15818,2018,A2 .
[4]Patent: WO2018/64135,2018,A1 .
[5]Patent: US2011/65700,2011,A1 .
[6]Patent: CN110156785,2019,A .

10
[ 25408-61-1 ]
[ 4498-72-0 ]
(E)-3-(dimethylamino)-1-(1H-3-indazolyl)-2-propen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 9h;Heating / reflux;	A total of 5.0 g of 1H-indazole as a starting material was subjected to bromination and tert-butoxycarbonylation by the procedures of Production Examples I-26-a and I-26-b, was acetylated at the 3-position by the procedure of Production Example I-29-a, to give 2.5 g of tert-butyl 3-acetyl-1H-1-indazolecarboxylate. A total of 1.5 g of this product was treated with 5 N hydrochloric acid by the procedure of Production Example I-25-b and thereby yielded 860 mg of 1-(1H-3-indazolyl)ethanone. A solution of 240 mg of this product and 0.4 ml of N,N-dimethylformamide dimethylacetal in 5 ml toluene was heated under reflux for 9 hours. The solvent was evaporated, and the residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane = 2:1), to give 88 mg of the title compound as a colorless powder.1H-NMR(400MHz, DMSO-d6) d 2.88 (3H, bs), 3.13 (3H, bs), 6.08 (1H, d, J = 13.1 Hz), 7.19 (1H, t, J = 7.6 Hz), 7.36 (1H, t, J = 7.6 Hz), 7.56 (1H, d, J = 7.6 Hz), 7.72 (1H, d, J = 13.1 Hz), 8.26 (1H, d, J = 7.6 Hz), 13.37 (1H, s)

References: [1]Patent: EP1380576,2004,A1 .Location in patent: Page 74.

11
[ 4498-72-0 ]
[ 358780-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In 1,4-dioxane;	d) <strong>[4498-72-0]1-(1H-indazol-3-yl)ethanone</strong> (0.01 mol) was stirred in 1,4-dioxane (100 ml), at room temperature. A solution of Br2 (0.01 mol) in 1,4-dioxane (20 ml) was added dropwise and the resulting reaction mixture was stirred overnight at room temperature. The precipitate was filtered off and the filtrate was evaporated. The residue was crystallized from CH3OH, filtered off and dried. Yield: 0.73 g of 2-bromo-<strong>[4498-72-0]1-(1H-indazol-3-yl)ethanone</strong> (interm. 10).
	With copper bromide; In ethyl acetate; for 4h;Reflux;	7.4 2-Bromo-<strong>[4498-72-0]1-(1H-indazol-3-yl)ethanone</strong>In a round-bottomed flask, 4.5 g of copper bromide are placed in 180 ml of ethyl acetate and the mixture is refluxed. 1.6 of <strong>[4498-72-0]1-(1H-indazol-3-yl)ethanone</strong> are added. The mixture is stirred for 4 hours at reflux. The resulting mixture is filtered through paper and the filtrate is poured into 150 ml of a 20percent solution of sodium thiosulphate. The mixture is extracted with 60 ml of ethyl acetate. The organic phase is washed with 40 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. 2.4 g of compound are obtained.1H NMR (DMSO-d6, delta in ppm): 4.95 (s, 2H); from 7.35 to 7.55 (m, 2H); 7.75 (d, 1H); 8.2 (d, 1H); 14.1 (s, 1H). M+H=239.

References: [1]Patent: US2003/203897,2003,A1 .
[2]Patent: US2011/65700,2011,A1 .Location in patent: Page/Page column 17.

12
[ 1634-04-4 ]
[ 4498-72-0 ]
[ 243118-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; Chlorodifluoromethane; Petroleum ether;	Example (V-1) At 70° C., chlorodifluoromethane is introduced for 3 hours into a mixture of 36.8 g (0.23 mol) of <strong>[4498-72-0]1-(1H-indazol-3-yl)-ethanone</strong> and 38.5 g of potassium carbonate in 400 ml of dimethylformamide. The mixture is then poured into 1.51 of ice-water and the precipitated product is filtered off with suction. The crude product is chromatographed over silica gel using petroleum ether/methyl t-butyl ether (6:1). This gives 27 g (56percent of theory) of 1-(1-difluoromethyl-1H-indazol-3-yl)-ethanone. HPLC: logP=2.67

References: [1]Patent: US6462039,2002,B1 .

13
C₁₁H₁₁N₅O [ No CAS ]
[ 14722-38-4 ]
[ 4498-72-0 ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 219 - 222.

14
[ 4498-72-0 ]
[ 1198473-42-5 ]

References: [1]Patent: US2011/65700,2011,A1 .

15
[ 4498-72-0 ]
[ 1198473-44-7 ]

References: [1]Patent: US2011/65700,2011,A1 .

16
[ 4498-72-0 ]
[ 1415509-34-0 ]