[ CAS No. 877773-17-6 ] {[proInfo.proName]}

Name: 877773-17-6|Methyl 6-(trifluoromethyl)-1H-indazole-3-carboxylate|98%
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SKU: A716514
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Quality Control of [ 877773-17-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 877773-17-6 ]

SDS Specification

Alternatived Products of [ 877773-17-6 ]

Product Details of [ 877773-17-6 ]

CAS No. :	877773-17-6	MDL No. :	MFCD09878903
Formula :	C₁₀H₇F₃N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VSKCVMICQDVGNJ-UHFFFAOYSA-N
M.W :	244.17	Pubchem ID :	53408454
Synonyms :

Calculated chemistry of [ 877773-17-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.38
TPSA :	54.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.68
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	3.52
Log Po/w (MLOGP) :	2.04
Log Po/w (SILICOS-IT) :	2.87
Consensus Log Po/w :	2.55

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.2
Solubility :	0.155 mg/ml ; 0.000634 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0919 mg/ml ; 0.000376 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.88
Solubility :	0.0322 mg/ml ; 0.000132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 877773-17-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 877773-17-6 ]

* 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 [ 877773-17-6 ]

[ 877773-17-6 ] Synthesis Path-Downstream 1~20

1
[ 877773-17-6 ]
[ 94-99-5 ]
[ 877766-37-5 ]
[ 877773-19-8 ]

Yield	Reaction Conditions	Operation in experiment
80%; 15%	With potassium carbonate;tetra-(n-butyl)ammonium iodide; In acetonitrile; at 90℃; for 1 - 2h;Heating / reflux;	Step 5: 1-(2,4-Dichlorobenzyl)-6-trifluoromethyl-1H-indazole-3-carboxylic Acid methyl ester 6-Trifluoromethyl-1H-indazole-3-carboxylic acid methyl ester (2.75 g, 0.0112 mol) was dissolved in acetonitrile (50 mL), and potassium carbonate (10 g, 0.07 mol), <strong>[94-99-5]2,4-dichlorobenzyl chloride</strong> (2.42 g, 0.01239 mol) and tetrabutylammonium iodide (catalytic) were added. The reaction mixture was heated to reflux and refluxed for 2 h under good stirring. The progress of the reaction was monitored by TLC. After completion of the reaction, potassium carbonate was filtered while hot and then washed with acetone. The combined solvents were distilled off under reduced pressure to afford the crude mixture of N1 and N2 benzylated products. The isomers were separated by column chromatography (silica gel, eluent started with hexane then changed to 8:2 hexane, ethyl acetate). 1-(2,4-Dichlorobenzyl)-6-trifluoromethyl-1H-indazole-3-carboxylic acid methyl ester. Yield: 3.62 g (80%), white crystals mp 118-120 C. 1H NMR (CDCl3) 8.39 (d, J=8.4 Hz, 1H) 7.74 (s, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.45 (d, J=2.1 Hz, 1H), 7.12 (dd, J=8.4 and 2.1 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 5.82 (s, 2H), 4.07 (s, 3H). MS (FAB) m/z: 403 (M++1).
	With tetra-(n-butyl)ammonium iodide; potassium carbonate; In acetonitrile; at 90℃;	Step 5: l-(2,4-Dichlorobenzyl)-6-trifluoromethyl-lH-indazole-3-carboxylic Acid methyl ester. -Trifluoromethyl-lH-indazole-S-carboxylic acid methyl ester (2.75 g, 0.0112 mol) was dissolved in acetonitrile (50 mL), and potassium carbonate (10 g, 0.07 mol),<strong>[94-99-5]2,4-dichlorobenzyl chloride</strong> (2.42 g, 0.01239 mol) and tetrabutylammonium iodide (catalytic) were added. The reaction mixture was heated to reflux and refluxed for 2 h under good stirring. The progress of the reaction was monitored by TLC. After completion of the reaction, potassium carbonate was filtered while hot and then washed with acetone. The combined solvents were distilled off under reduced pressure to afford the crude mixture of Nl and N2 benzylated products. The isomers were separated by column chromatography (silica gel, eluent started with hexane then changed to 8:2 hexane, ethyl acetate).l-(2,4-Dichlorobenzyl)-6-trifluoromethyl-lH-indazole-3-carboxylic acid methyl ester. Yield: 3.62 g (80%), white crystals mp 118-120 0C. J H NMR (CDCl3)8.39 (d, J = 8.4 Hz, 1 H) 7.74 (s, 1 H), 7.57 (d, J = 8.4 Hz, 1 H), 7.45 (d, J = 2.1 Hz, 1 H), 7.12 (dd, J = 8.4 and 2.1 Hz, 1 H), 6.78 (d, J = 8.4 Hz, 1 H), 5.82 (s, 2 H), 4.07 (s, 3 H).MS (FAB) m/z: 403 (M+ + 1).2-(2,4-Dichlorobenzyl)-6-trifluoromethyl-2H-indazole-3-carboxylic acid methyl ester. Yield: 680 mg (15%), white crystals mp 132-134 0C. * H NMR (DMSO- d-6) 8.27 (s, 1 H), 8.20 (d, J = 8.7 Hz, 1 H), 7.76 (d, J = 1.8 Hz, 1 H), 7.57 (d, J = 8.7 Hz, 1 H), 7.30 (dd, J = 8.3 and 1.8 Hz, 1 H), 6.78 (d, J = 8.3 Hz, 1 H), 6.17 (s, 2 H), 3.96 (s, 3H).

Reference： [1]Patent: US2006/47126,2006,A1 .Location in patent: Page/Page column 27-28
[2]Patent: WO2011/5759,2011,A2 .Location in patent: Page/Page column 72-73

2
(2-acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester [ No CAS ]
[ 877773-17-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tert.-butylnitrite; acetic acid at 90 - 95℃; for 1.83333 - 2h;	2.4 Step 4: 6-Trifluoromethyl-1H-indazole-3-carboxylic acid methyl ester To a solution of (2-acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester (16 g, 0.058 mol) in acetic acid (50 mL) was added dropwise t-butyl nitrite (90%) (7.35 g, 0.063 mol) over a period of 20 min. at 90-95° C. The mixture was then stirred for 0.5 h at 95° C., poured into cold water and stirred for 1 h. The precipitates were collected by filtration and washed with water. The crude material was dissolved in ethyl acetate and dried over sodium sulfate. The solvent was removed in vacuo. This material (13.4 g, 95%) was used without further purification in the next step. A small sample was crystallized from ethyl acetate to yield a white solid, mp 240-242° C. 1H NMR (DMSO-d-6) 8.25 (d, J=8.5 Hz, 1H), 8.04 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 3.95 (s, 3H). MS (FAB) m/z: 245.1 (M++1).
	With tert.-butylnitrite; acetic acid at 90 - 95℃; for 2.16667h; Cooling with ice;	2.4 Step 4: 6-Trifluoromethyl-lH-indazole-3-carboxylic acid methyl ester.To a solution of (2-acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester (16 g, 0.058 mol) in acetic acid (50 mL) was added dropwise t-butyl nitrite (90%) (7.35 g, 0.063 mol) over a period of 20 min. at 90-95 0C. The mixture was then stirred for 0.5 h at 95 0C, poured into cold water and stirred for 1 h. The precipitates were collected by filtration and washed with water. The crude material was dissolved in ethyl acetate and dried over sodium sulfate. The solvent was removed in vacuo. This material (13.4 g, 95%) was used without further purification in the next step. A small sample was crystallized from ethyl acetate to yield a white solid, mp 240-242 0C. 1H NMR (DMSO- d-6) 8.25 (d, J = 8.5 Hz, 1 H), 8.04 (s, 1 H), 7.58 (d, J = 8.5 Hz, 1 H), 3.95 (s, 3 H). MS (FAB) m/z: 245.1 (M+ + 1).

Reference： [1]Current Patent Assignee: UNIVERSITY OF KANSAS - US2006/47126, 2006, A1 Location in patent: Page/Page column 27
[2]Current Patent Assignee: UNIVERSITY OF KANSAS - WO2011/5759, 2011, A2 Location in patent: Page/Page column 72

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[ 121-17-5 ]
[ 877773-17-6 ]