201286-95-5|Methyl 3-methyl-2H-indazole-6-carboxylate| Ambeed

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Quality Control of [ 201286-95-5 ] Purity: 97% SDS Specification

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Product Details of [ 201286-95-5 ]

CAS No. :	201286-95-5
Formula :	C₁₀H₁₀N₂O₂
M.W :	190.20
SMILES Code :	O=C(C1=CC2=NNC(C)=C2C=C1)OC
MDL No. :	MFCD22628066
InChI Key :	CKPSQUXIPHAGLQ-UHFFFAOYSA-N
Pubchem ID :	22387979

Safety of [ 201286-95-5 ]

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

Computational Chemistry of [ 201286-95-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	9
Fraction Csp3	0.2
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	52.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.98 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.6
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	1.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.66
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.	1.34
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	2.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.597 mg/ml ; 0.00314 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.	-2.58
Solubility	0.496 mg/ml ; 0.00261 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	-3.38
Solubility	0.0798 mg/ml ; 0.00042 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	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)	1.69

Application In Synthesis of [ 201286-95-5 ]

* 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 [ 201286-95-5 ]

[ 201286-95-5 ] Synthesis Path-Downstream 1~33

1
[ 201286-95-5 ]
[ 92059-86-4 ]
1-(2-chloro-4-phenylbenzyl)-6-(methoxycarbonyl)-3-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride;	Preparation Example 60-1 1-(2-Chloro-4-phenylbenzyl)-<strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> In the same manner as in Preparation Example 39-5, a crude product of the object compound (1.10 g) was obtained from <strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> (0.475 g), 60% sodium hydride (0.10 g) and 2-chloro-4-phenylbenzyl bromide (0.70 g).. The crude product was used in the next step without purification. 1H-NMR(CDCl3, delta ppm): 2.64(3H, s), 3.94(3H, s), 5.73(2H, s), 6.74(1H, d, J=8.1 Hz), 7.31(1H, dd, J=8.1 and 1.8 Hz), 7.33-7.38(1H, m), 7.42(2H, t, J=7.5 Hz), 7.50-7.53(2H, m), 7.64-7.67(2H, m), 7.74(1H, d, J=8.4 Hz), 7.82(1H, dd, J=8.4 and 1.3 Hz), 8.13(1H, s)

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 96.

2
[ 201286-95-5 ]
[ 92059-86-4 ]
2-(2-chloro-4-phenylbenzyl)-6-(methoxycarbonyl)-3-methyl-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; ethyl acetate; at 70℃; for 14h;	Preparation Example 152-1 2-(2-Chloro-4-phenylbenzyl)-6-(methoxycarbonyl)-3-methyl-2H-indazole A mixture of <strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> (1.90 g), 2-chloro-4-phenylbenzyl bromide (3.37 g), potassium carbonate (2.76 g), ethyl acetate(10 ml) and water (5 ml) was stirred for 14 hr at 70 C. Hexane and water were added, and the precipitated solid was collected by filtration and washed with a mixed solvent of ethyl acetate and hexane (2/3).. This was dried under reduced pressure to give the objective compound (1.02 g). 1H-NMR (CDCl3, delta ppm): 2.61(3H, s), 3.96(3H, s), 5.77(2H, s), 6.66(1H, d, J=8.1 Hz), 7.33-7.39(2H, m), 7.43(2H, t, J=7.6 Hz), 7.51(2H, d, J=7.5 Hz), 7.62-7.66(2H, m), 7.69(1H, d, J=8.8 Hz), 8.49(1H, s)

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 168.

3
[ 201286-95-5 ]
[ 185315-49-5 ]
1-(4-bromo-2-chlorobenzyl)-6-(methoxycarbonyl)-3-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride;	Preparation Example 61-1 1-(4-Bromo-2-chlorobenzyl)-<strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> In the same manner as in Preparation Example 39-5, a crude product of the object compound (2.00 g) was obtained from <strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> (0.63 g), 60% sodium hydride (0.13 g) and 4-bromo-2-chlorobenzyl chloride (1.30 g).. The crude product was used in the next step without purification.

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 97.

4
[ 67-56-1 ]
[ 201286-96-6 ]
[ 201286-95-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid; for 22h;Heating / reflux;	Preparation Example 39-4 6-(Methoxycarbonyl)-3-methyl-1H-indazole 6-Carboxy-3-methyl-1H-indazole (359 mg, 2.11 mmol) was dissolved in methanol (50 ml), and concentrated sulfuric acid (0.1 ml) was added.. The mixture was heated under reflux for 22 hr.. After cooling, a saturated aqueous sodium hydrogencarbonate solution was added and the methanol was distilled away under reduced pressure.. The residue was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.. The drying agent was filtered off and the filtrate was concentrated under reduced pressure to give the objective compound (340 mg, 87%) as brown crystals. 1H-NMR(CDCl3, delta ppm): 8.18(1H, s), 7.82(1H, d, J=8.4 Hz), 7.72(1H, d, J=8.4 Hz), 3.96(3H, s), 2.61(3H, s).

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 81.

5
[ 201286-95-5 ]
[ 100-39-0 ]
[ 201286-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone;	(a) Methyl 1-benzyl-3-methyl-1 H-indazole-6-carboxylate A solution of <strong>[201286-95-5]methyl 3-methyl-indazole-6-carboxylate</strong> (0.2 g, Reference Example 44) in acetone (15 ml) was treated with benzyl bromide (0.898 g) then with potassium carbonate (0.290 g) and a catalytic amount of 18-crown-6. The mixture was stirred for 12 hours at room temperature then poured into water (30 ml) and then extracted three times with ethyl acetate (30 ml). The combined extracts were dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluding with a mixture of ethyl acetate and hexane (7:1, v/v) to yield the title compound (0.161 g) and methyl 2-benzyl-3-methyl-indazole-6-carboxylate (0.069 g).

References: [1]Patent: US6303600,2001,B1 .

6
[ 201286-96-6 ]
[ 201286-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol;	REFERENCE EXAMPLE 44 Methyl 3-methyl-1 H-indazole-6-carboxylate A solution of 3-methyl-indazole-6-carboxylic acid (1.57 g, Reference Example 45) in methanol (75 ml) was treated with hydrogen chloride gas for 10 minutes. The reaction mixture was stirred for 12 hours at room temperature then evaporated. The residue was partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml). The combined extracts were dried over sodium sulphate then evaporated. The residue was washed with hexane to give the title compound (1.56 g) which was used without further purification.

References: [1]Patent: US6303600,2001,B1 .

7
[ 201286-95-5 ]
[ 94-99-5 ]
1-(2,4-Dichlorobenzyl)-6-(methoxycarbonyl)-3-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		Preparation Example 39-5 1-(2,4-Dichlorobenzyl)-<strong>[201286-95-5]6-(methoxycarbonyl)-3-methyl-1H-indazole</strong> 6-(Methoxycarbonyl)-3-methyl-1H-indazole (0.40 g, 2.1 mmol) was dissolved in dimethylformamide (15 ml) and the mixture was ice-cooled.. sodium hydride (85 mg, 60% suspension in oil, 2.1 mmol as NaH) was added and the mixture was stirred at 0 C. for 30 min. 2,4-Dichlorobenzyl chloride (0.45 g, 2.3 mmol) was added and the mixture was stirred at room temperature for 18 hr.. The reaction mixture was extracted with ethyl acetate/water.. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.. The drying agent was filtered off and the filtrate was concentrated under reduced pressure.. The obtained crystalline residue was separated and purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to give the objective compound (0.54 g, 74%) as colorless crystals. 1H-NMR(CDCl3, delta ppm): 8.06(1H, d, J=1.1 Hz), 7.82(1H, dd, J=1.1 and 8.4 Hz), 7.72(1H, d, J=8.3 Hz), 7.42(1H, d, J=2.0 Hz), 7.08(1H, dd, J=2.0 and 8.3 Hz), 6.60(1H, d, J=8.4 Hz), 5.63(2H, s), 3.94(3H, s), 2.61(3H, s)

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 81.

8
[ 24812-93-9 ]
[ 201286-95-5 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 2-12:Methyl 3-methyl-lH-indazole-6-carboxylateAc2theta (0.579 ml, 6.14 mmol) was added to a stirred mixture of KOAc (361 mg, 3.68 mmol) and methyl 3-amino-4-ethylbenzoate (550mg, 3.07 mmol) in CEtaCI3 (5 ml) and the mixture was stirred at 900C for 2h. KOAc (361 mg, 3.68 mmol), 18-crown-6 ether (81 mg, 0.307 mmol) and isobutylnitrate (719 mg, 6.14 mmol) were added thereto at room temperature and the mixture was further stirred at 900C for 2 h. The reaction mixtuer was diluted with chloroform and H2O, the organic layer was washed with water, brine, and dried over MgSOphi After filteration and evaporation, the residue was diluted with THF (5.00 ml) and MeOH (5.00 ml), and K2CO3 (848 mg, 6.14 mmol) was added thereto at room temperature. After the mixture was stirred for 2h. at room temperature, CHCI3 and H2O was added thereto. The organic layer was washed with H2O, brine, and dried over MgSOphi After filteration and evaporation, the residi was puritied by silicagel column chromatography (hexane / EtOAc) to give intended compound as a pale brown solid.

References: [1]Patent: WO2010/2010,2010,A1 .Location in patent: Page/Page column 84-85.

9
[ 24812-93-9 ]
[ 108-24-7 ]
[ 201286-95-5 ]

Yield	Reaction Conditions	Operation in experiment
48%		The compound obtained from Preparation Example 86-3 was dissolved in chloroform (50ml), and potassium acetate (6.4g, 65.28mmol) was added thereto. The nixture was cooled to 0. Acetic anhydride (16.7g, 163.2mmol) was added dropwise, and the reaction solution was diluted with chloroform (100ml). After adding dropwise isoamylnitrite (12.8g, 108.8mmol), the solution was stirred for 18 hours under reflux. The solution was cooled to room temperature, distilled under reduced pressure to remove the solvent. The residue was dissolved in dichloromethane and washed with brine, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and the residue was dissolved in tetrahydrofuran (100ml). 6N sodium hydroxide (20ml) was added thereto, and the solution was stirred for 2 hours and then extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (5.90g, 48%). [1169] NMR:1H-NMR(500HMz, CDCl3); delta 8.18 (s, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 3.96 (s, 3H), 2.61 (s, 3H)

References: [1]Patent: WO2014/73904,2014,A1 .Location in patent: Paragraph 1166-1169.

10
[ 103440-95-5 ]
[ 201286-95-5 ]

References: [1]Patent: WO2014/73904,2014,A1 .
[2]Patent: US6348474,2002,B1 .

11
[ 619-64-7 ]
[ 201286-95-5 ]

References: [1]Patent: WO2014/73904,2014,A1 .
[2]Patent: US6348474,2002,B1 .

12
[ 51885-79-1 ]
[ 201286-95-5 ]