50593-30-1|2-Methyl-2H-indazol-6-amine| Ambeed

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Quality Control of [ 50593-30-1 ] Purity: 97% SDS Specification

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Product Details of [ 50593-30-1 ]

CAS No. :	50593-30-1
Formula :	C₈H₉N₃
M.W :	147.18
SMILES Code :	NC1=CC2=NN(C)C=C2C=C1
MDL No. :	MFCD00464866
InChI Key :	MHCWLERQNFATHZ-UHFFFAOYSA-N
Pubchem ID :	590220

Safety of [ 50593-30-1 ]

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

Computational Chemistry of [ 50593-30-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	45.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.3
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	1.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.16
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.	0.84
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	0.71
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.15
Solubility	1.05 mg/ml ; 0.00715 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.	-1.77
Solubility	2.51 mg/ml ; 0.017 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	-2.09
Solubility	1.19 mg/ml ; 0.00807 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.	-6.31 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)	1.48

Application In Synthesis of [ 50593-30-1 ]

* 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 [ 50593-30-1 ]

[ 50593-30-1 ] Synthesis Path-Downstream 1~35

1
[ 50593-30-1 ]
[ 1147550-11-5 ]
2-methyl-5-thiocyanato-2<i>H</i>-indazol-6-ylamine [ No CAS ]

References: [1]Patent: US1876930,1929, .

2
[ 6850-22-2 ]
[ 50593-30-1 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 12.0h;	General procedure: 10% Palladium carbon (water content 51.7%, 1 g) was added to a solution of 2a (7.50 g, 40 mmol) in ethanol (150 ml), and the mixture was stirred under hydrogen atmosphere at room temperature for 12 h. The catalyst was removed by filtration and washed with ethanol. The filtrate and washings were combined and the solvent was distilled off under reduced pressure to give 3a as alight beige solid (6.05, 95.0% yield).

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1108 - 1110.
[2]Chemistry of Heterocyclic Compounds,1988,p. 403 - 409.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 491 - 498.
[3]Journal of Chemical Research, Miniprint,1990,p. 2601 - 2615.
[4]Heterocycles,1995,vol. 41,p. 487 - 496.
[5]Journal of the Chemical Society,1955,p. 2412,2419.
[6]Chinese Chemical Letters,2014,vol. 25,p. 989 - 994.

3
[ 39116-24-0 ]
[ 50593-30-1 ]
[ 112635-19-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 436 - 439.

4
[ 50593-30-1 ]
[ 119-53-9 ]
[ 112635-17-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 436 - 439.

5
[ 50593-30-1 ]
[ 16463-38-0 ]
[ 132283-43-3 ]

References: [1]Journal of Chemical Research, Miniprint,1990,p. 2601 - 2615.

6
[ 50593-30-1 ]
[ 87-13-8 ]
[ 69627-90-3 ]

References: [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 119 - 124.
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645.

7
[ 50593-30-1 ]
[ 52470-67-4 ]

References: [1]Chemistry of Heterocyclic Compounds,1988,p. 403 - 409.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 491 - 498.

8
[ 50593-30-1 ]
[ 28899-97-0 ]
2-methyl-6-phenylamino-1H-indazole [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 487 - 496.

9
[ 50-00-0 ]
[ 50593-30-1 ]
C₁₉H₁₈N₆ [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 2233 - 2240.

Yield	Reaction Conditions	Operation in experiment
	With iron; ammonium chloride; In ethanol; water;Reflux;	General procedure: [000414j The title compound has been synthesized by following the general procedure described above for reduction using the nitro compound 2 and Fe/NH4C1.

11
2-methyl-6-nitro-indazole [ No CAS ]
[ 50593-30-1 ]

References: [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227.
[2]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

12
[ 6850-22-2 ]
6-amino-7-chloro-2-methyl-2H-indazole [ No CAS ]
[ 50593-30-1 ]

References: [1]Heterocycles,2006,vol. 68,p. 2595 - 2605.

13
[ 77-78-1 ]
[ 7597-18-4 ]
[ 50593-30-1 ]
[ 74728-65-7 ]

References: [1]Heterocycles,2006,vol. 68,p. 2595 - 2605.

14
[ 7597-18-4 ]
[ 50593-30-1 ]

References: [1]Heterocycles,2006,vol. 68,p. 2595 - 2605.
[2]Chemistry of Heterocyclic Compounds,1988,p. 403 - 409.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 491 - 498.
[3]Journal of Chemical Research, Miniprint,1990,p. 2601 - 2615.
[4]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1108 - 1110.
[5]Chinese Chemical Letters,2014,vol. 25,p. 989 - 994.

15
[ 50593-30-1 ]
[ 69628-02-0 ]

References: [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 119 - 124.

16
[ 50593-30-1 ]
[ 69627-95-8 ]

References: [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 119 - 124.

17
[ 50593-30-1 ]
[ 65642-40-2 ]

References: [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 119 - 124.

18
[ 50593-30-1 ]
2-methyl-6-hydroxy-7-nitrosoindazole [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1988,p. 403 - 409.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 491 - 498.

19
[ 50593-30-1 ]
[ 132283-51-3 ]

References: [1]Journal of Chemical Research, Miniprint,1990,p. 2601 - 2615.

20
[ 50593-30-1 ]
[ 128056-60-0 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645.

21
[ 50593-30-1 ]
[ 128056-51-9 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645.

22
[ 50593-30-1 ]
[ 474799-56-9 ]
[ 474799-57-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 4-methyl-morpholine; HATU; In DMF (N,N-dimethyl-formamide); at 20℃; for 16.0h;	0.500 g (1.6 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid, 0.471 g (3.2 mmol) of 2-methyl-2H-indazol-6-ylamine, 0.4 ml (3.68 mmol) of N-methylmorpholine and 0.729 g (1.92 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HATU) in 25 ml of dimethylformamide are stirred for 16 hours at room temperature. The dimethylformamide is drawn off in an oil pump vacuum. The remaining residue is drawn off in saturated sodium bicarbonate solution. It is extracted three times with ethyl acetate, and the combined organic phases are dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with a gradient that consists of hexane:acetone=100:0 to 50:50 as an eluant. 0.669 g (96% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide is obtained in the form of a beige foam.

References: [1]Patent: US2005/54654,2005,A1 .Location in patent: Page/Page column 38.

23
[ 50593-30-1 ]
2-[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl ester [ No CAS ]
N-(2-methyl-2H-indazol-6-yl)-2-[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	trimethylaluminum; In 1,2-dichloro-ethane; toluene; at 0 - 85℃; for 10.0h;	A suspension of 2-methyl-2H-indazol-6-ylamine [Davies J. Chem. Soc.; 1955; 2412-2419] (809 mg, 5.5 mmol) in DCE (13.5 mL) was treated at 0 C consecutively with, trimethylaluminium (2 M) in toluene (4.23 mL, 8.46 mmol), 2-[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl ester (1.34 mg, 4.23 mmol) and DCE (20 mL). The reaction mixture was placed under a nitrogen atmosphere and heated for 10 hours at 85 C (bath temperature). On cooling the reaction was poured into aqueous sodium-potassium tartrate solution (150 mL) and partitioned between EtOAc and water. The organic phase was washed with brine, dried, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (Gradient elution: 100% CH2Cl2 to 90% CH2Cl2/10% MeOH) to give N-(2-methyl-2H-indazol-6-yl)-2-[2-(3-methylureido)-pyridin-4-ylmethyl]-amino}-nicotinamide (964 mg, 53%) as a solid; Mp. 205-207 C.

References: [1]Patent: EP1655297,2006,A1 .Location in patent: Page/Page column 12.

24
[ 50593-30-1 ]
[ 118-48-9 ]
[ 1064152-85-7 ]