677702-36-2|5-Nitro-1H-indazole-3-carbaldehyde| Ambeed

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Quality Control of [ 677702-36-2 ] Purity: 98% SDS Specification

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Product Details of [ 677702-36-2 ]

CAS No. :	677702-36-2
Formula :	C₈H₅N₃O₃
M.W :	191.14
SMILES Code :	[N+](=O)([O-])C2=CC=C1[NH]N=C(C1=C2)C=O
MDL No. :	MFCD07781436
InChI Key :	UVUPPLXBIXJRKD-UHFFFAOYSA-N
Pubchem ID :	21409181

Safety of [ 677702-36-2 ]

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

Computational Chemistry of [ 677702-36-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	50.3
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	91.57 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.12
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	1.18
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.28
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.	-0.53
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	-0.04
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.11
Solubility	1.48 mg/ml ; 0.00772 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.	-2.7
Solubility	0.383 mg/ml ; 0.002 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	-2.24
Solubility	1.09 mg/ml ; 0.00571 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	No
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.	-6.63 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	3.0 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)	1.68

Application In Synthesis of [ 677702-36-2 ]

* 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 [ 677702-36-2 ]

[ 677702-36-2 ] Synthesis Path-Downstream 1~35

2
[ 773-64-8 ]
[ 677702-36-2 ]
[ 677702-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In dichloromethane; at 0 - 20℃;	Under argon, 4-dimethylaminopyridine (3.63 g, 29.71 mmol) is added to a solution of intermediate 15.1 (5.4 g, 28.25 mmol) in anhydrous CH2Cl2 (250 ml) kept at 0 C. by an ice bath, followed after a few minutes, dropwise by 2-mesitylenesulphonyl chloride (6.50 g, 29.71 mmol) in solution in CH2Cl2 (100 ml). The reaction mixture is stirred for 1 h at 0 C. and then overnight at room temperature. Water is added. The reaction mixture is extracted with CH2Cl2. The organic phase is washed with brine, dried over Na2SO4 and evaporated to give a brown solid which is purified by chromatography on silica gel (300 g), eluding with CH2Cl2. A solid separates after concentrating the fractions under vacuum. It is filtered and then washed with diethyl ether and petroleum ether. 5 g of product are obtained in the form of a beige solid.

References: [1]Patent: US2006/4000,2006,A1 .Location in patent: Page/Page column 17.

3
[ 68-12-2 ]
[ 5401-94-5 ]
[ 677702-36-2 ]

Yield	Reaction Conditions	Operation in experiment
92%		POCl3 (67.43 mmol) was added dropwise to a stirred solution of 40 cm3 DMF at 0-5 C over a period of15 min. The reaction mixture was allowed on stirring for half an hour at the same temperature. 5-Nitroazaindole(10 g, 61.3 mmol) was dissolved in 10 cm3 DMF and added dropwise to the above Vilsmeier reagent at 0-5 C.Now the reaction mixture was allowed to stand for 3 h at room temperature. The completion of the reaction was known by monitoring the HPLC. The oily residue was poured into crushed ice and NaOH solution was added to this reaction mixture. Yellow color solid was precipitated,filtered, and recrystalized from hot ethanol. Yellow colorsolid; 92 % yield (10.77 g); m.p.: 215-217 C; IR (neat):m = 3545, 1624, 1537, 1488, 1337, 949, 786,744 cm-1; 1HNMR (DMSO-d6, 400 MHz): d = 13.74 (bs, 1H, NH),8.84 (s, 1H), 8.41 (s, 1H), 8.21-8.18 (d, 1H, J = 10.4 Hz),7.74-7.72 (d, 1H, J = 9.2 Hz) ppm; 13C NMR (DMSO-d6,100 MHz): d = 110, 118, 120, 121, 136, 141, 168 ppm;MS (ESI): m/z = 192 ([M+H]+).

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

4
[ 677702-36-2 ]
N'-[(E)-(5-methoxy-1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

5
[ 677702-36-2 ]
N'-[(E)-(5-methoxy-1-methyl-1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

6
[ 677702-36-2 ]
5-nitro-N'-[(E)-(5-nitro-1H-indazol-3-yl)methylidene]-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

7
[ 677702-36-2 ]
[ 78155-76-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium permanganate; In acetone; at 20℃; for 6h;	KMnO4 (15 g, 94.91 mmol) was soluble in 300 cm3 water and added dropwise at room temperature to a reaction mixture of 52.35 mmol of 5 soluble in 1000 cm3 acetone.The reaction mixture was stirred at room temperature for 6 h. Later, 50 cm3 of 30 % H2O2 was added dropwise to neutralize the KMnO4. The reaction mixture was filtered to remove the KMnO4 and the reaction mass was concentrated by vacuum. The concentrated mass was acidified by conc. HCl, filtered, and recrystallized from methanol to afford 6. Yellow color solid; yield 79 % (8.56 g); m.p.:191-193 C.

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

8
[ 677702-36-2 ]
[ 78155-75-6 ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

9
[ 677702-36-2 ]
5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

10
[ 677702-36-2 ]
N'-[(E)-(1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

11
[ 677702-36-2 ]
N'-[(E)-(1-methyl-1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

12
[ 677702-36-2 ]
N'-[(E)-(5-bromo-1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

13
[ 677702-36-2 ]
N'-[(E)-(5-bromo-1-methyl-1H-indol-3-yl)methylidene]-5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

14
[ 677702-36-2 ]
5-nitro-N'-[(E)-(5-nitro-1H-indol-3-yl)methylidene]-1H-indazole-3-carbohydrazide [ No CAS ]

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

15
[ 677702-36-2 ]
[ 56559-62-7 ]
1-methyl-N'-[(Z)-(5-nitro-1H-indazol-3-yl)methylidene]-1H-indole-3-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With acetic acid; at 90℃;	General procedure: 5-Nitro-1H-indazole-3-carbohydrazide (8, 500 mg,2.26 mmol, 1.0 eq.) was dissolved in 3 cm3 glacial acetic acid. To this reaction mixture 2.26 mmol indole-3-aldehyde(1.0 eq.) was added and heated at 90 C for 6 h. Later the reaction mass was neutralized with a cold NaHCO3 solution, filtered, and recrystallized from ethanol to afford 10a.

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

16
[ 677702-36-2 ]
5-bromo-1-methyl-1H-indole-3-carbohydrazide [ No CAS ]
5-bromo-1-methyl-N'-[(Z)-(5-nitro-1H-indazol-3-yl)methylidene]-1H-indole-3-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic acid; at 90℃;	General procedure: 5-Nitro-1H-indazole-3-carbohydrazide (8, 500 mg,2.26 mmol, 1.0 eq.) was dissolved in 3 cm3 glacial acetic acid. To this reaction mixture 2.26 mmol indole-3-aldehyde(1.0 eq.) was added and heated at 90 C for 6 h. Later the reaction mass was neutralized with a cold NaHCO3 solution, filtered, and recrystallized from ethanol to afford 10a.

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

17
[ 677702-36-2 ]
5-nitro-1H-indazole-3-carbohydrazide [ No CAS ]
5-nitro-N'-[(E)-(5-nitro-1H-indazol-3-yl)methylidene]-1H-indazole-3-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With acetic acid; at 90℃;	General procedure: 5-Nitro-1H-indazole-3-carbohydrazide (8, 500 mg,2.26 mmol, 1.0 eq.) was dissolved in 3 cm3 glacial acetic acid. To this reaction mixture 2.26 mmol indole-3-aldehyde(1.0 eq.) was added and heated at 90 C for 6 h. Later the reaction mass was neutralized with a cold NaHCO3 solution, filtered, and recrystallized from ethanol to afford 10a.

References: [1]Monatshefte fur Chemie,2017,vol. 148,p. 305 - 314.

18
[ 110-87-2 ]
[ 677702-36-2 ]
5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; at 20℃; for 12h;	p-Toluene sulfonic acid (30 mg, 0.158 mmol) was added to a solution of 5-nitro-indazole-3-carbaldehyde 6 (R: nitro) (300 mg, 1.569 mmol) and 3,4-dihydro-2H-pyran (265 mg, 3.150 mmol) in a mixture of THF/ CH2Cl2 (1:1, 8 mL). The reaction mixture was stirred for 12 h at room temperature and then the solvent was removed in vacuo. The residue was taken in CH2Cl2 (50 mL) and poured in water (20 mL). The organic layer was separated, the aqueous layer was extracted with CH2Cl2 (50 mL), the combined organic layers were washed with water (40 mL) and brine (40 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (CH2Cl2) afforded 215 mg (50% yield) as a solid. 1H NMR (400 MHz, CDCl3): delta 10.23 (s, 1H), 9.23 (d, 1H, J = 2.0 Hz), 8.35 (dd, 1H, J = 2.0 and 9.2 Hz), 7.80 (d, 1H, J = 9.2 Hz), 5.89 (dd, 1H, J = 2.8 and 8.8 Hz), 3.98 (m, 1H), 3.80 (m, 1H), 2.53 (m, 1H), 2.19 (m, 2H), 1.76 (m, 3H).