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[ CAS No. 116369-23-4 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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DV 2D 3D

3d Animation Molecule Structure of 116369-23-4

Chemical Structure| 116369-23-4

Chemical Structure| 116369-23-4

Structure of 116369-23-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 116369-23-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 116369-23-4 ]

SDS Specification

Alternatived Products of [ 116369-23-4 ]

Product Details of [ 116369-23-4 ]

CAS No. :	116369-23-4	MDL No. :	MFCD09832254
Formula :	C₇H₅F₄NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HQUWXEXDIIWBBY-UHFFFAOYSA-N
M.W :	195.11	Pubchem ID :	14439308
Synonyms :

Calculated chemistry of [ 116369-23-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.49
TPSA :	35.25 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) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	4.0
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	2.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.24 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.191 mg/ml ; 0.000977 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.95
Solubility :	0.22 mg/ml ; 0.00113 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 116369-23-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	2810
Hazard Statements:	H302-H311-H315-H319-H332	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 116369-23-4 ]

* 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.

Upstream synthesis route of [ 116369-23-4 ]
Downstream synthetic route of [ 116369-23-4 ]

[ 116369-23-4 ] Synthesis Path-Upstream 1~2

1
[ 352-67-0 ]
[ 116369-23-4 ]
[ 123572-63-4 ]

Reference： [1] Patent: WO2011/22449, 2011, A1, . Location in patent: Page/Page column 46-47

2
[ 123572-62-3 ]
[ 124170-06-5 ]
[ 116369-23-4 ]
[ 123572-63-4 ]

Reference： [1] Patent: WO2004/46120, 2004, A2, . Location in patent: Page 191

[ 116369-23-4 ] Synthesis Path-Downstream 1~4

1
[ 116369-23-4 ]
[ 407-25-0 ]
[ 123572-63-4 ]
2,2,2-trifluoro-N-(2-fluoro-5-trifluoromethoxy-phenyl)-acetamide [ No CAS ]
[ 1346237-13-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; for 16h;	Without purification, the phenylamines (7 g, 35.8 mmol) were suspended in dichloromethane (100mL), treated with trifluoroacetic anhydride (71 mmol) and triethylamine (20 mL) for 16h. The reaction mixture was washed with saturated NaHCO3 and brine. The organic phase was further purified by silica gel chromatography (hexane/EtOAc 9:1) to give a mixture (5.29g) of 2,2,2-trifluoro-N-(5-fluoro-2-trifluoromethoxy-phenyl)-acetamide and its isomer in 1:4 ratio, which was nitrated in a same procedure as the first step.

Reference： [1]Patent: WO2004/46120,2004,A2 .Location in patent: Page 191

2
[ 123572-62-3 ]
[ 124170-06-5 ]
[ 116369-23-4 ]
[ 123572-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; under 2585.81 Torr; for 3.5h;	The crude nitration product (6.05 g) was dissolved in ethanol (40 mL) and shacked with 10% Pd/C (310 mg) and concentrate HCl (2.8 mL) under H2 (50 psi) for 3.5 h. Filtration and concentration gave a mixture (8.0g) of 5-fluoro-2-trifluoromethoxy-phenylamine and its isomer 2-fluoro-5-trifluoromethoxy-phenylamine in 3:1 ratio.

Reference： [1]Patent: WO2004/46120,2004,A2 .Location in patent: Page 191

3
[ 352-67-0 ]
[ 116369-23-4 ]
[ 123572-63-4 ]

Yield	Reaction Conditions	Operation in experiment
		A. 1 -Fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-Fluoro-2-nitro-1 - trifluoromethoxy-benzeneTo a mixture of <strong>[352-67-0]1-fluoro-4-trifluoromethoxy-benzene</strong> (31.57 g, 0.18 mol) in cone. H2SO4 (100 ml_) at 0C is added cone. HNO3 (30 ml_) dropwise over a 10 min period. After the mixture is stirred at 0 C for 1 h, it was poured into ice. The mixture is extracted with EtOAc. The organic extract is washed with H2O (3x) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 38 g (96%) of the product as a mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 8.00- 7.90 and 7.80-7.65 (m, 1 H), 7.60-7.25 (m, 2H); 19 F NMR (CDCI3) delta -57.59 and -58.11 (s, 3F), -109.07 and -117.90 (t, J = 6.2 and d, J = 6.2, 1 F).B. 2-Fluoro-5-trifluoromethoxy-phenylamine and 5-Fluoro-2-trifluoromethoxy- phenvlamine A mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene and Raney Ni (2800) in MeOH (250 ml_) is hydrogenated at 40 psi for 5 h (or until no more H2 is consumed). The catalyst is filtered off, and the filtrate is concentrated in vacuo. The residue is redissolved in CH2CI2, dried over MgSO4, filtered, and concentrated in vacuo to yield 27.4 g of the product (dark brown liquid) as a mixture of 2-fluoro-5-trifluoromethoxy-phenylamine and 5-fluoro-2- trifluoromethoxy-phenylamine (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 7.15-6.90 (m, 1 H), 6.70-6.30 (m, 2H), 3.60-4.25 (br m, 1 H); 19 F NMR (CDCI3) delta -57.77 and -57.86 (s, 3F), -113.83 and -137.09 (1 H); MS 196 (M+1 , 100%).

Reference： [1]Patent: WO2011/22449,2011,A1 .Location in patent: Page/Page column 46-47

4
[ 203314-28-7 ]
[ 116369-23-4 ]
2-(2,5-dibromophenyl)-N-(2-fluoro-5-(trifluoromethoxy)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate	132.A Step A: Step A: 2-(2,5-dibromophenyl)-N-(2-fluoro-5-(trifluoromethoxy)phenyl)acetamide To a stirred solution of 2-(2,5-dibromophenyl)acetic acid (1.00 g, 3.40 mmol) in pyridine (34.0 mL) was added HATU (1.36 g, 3.57 mmol), and the reaction mixture was allowed to stir at 50° C. for 30 minutes. 2-fluoro-5-(trifluoromethoxy)aniline (0.66 g, 3.40 mmol) was added via syringe, and the reaction mixture was allowed to stir at 50° C. for 16 h. The solvent was removed in vacuo. The residue was taken up in toluene, and the solvent was again removed in vacuo. The crude material was dry absorbed on SiO2 and subjected to flash silica gel column chromatography using a 0-40% EtOAc/hexanes gradient to afford the title compound. LC/MS=470 [M+1].
	Stage #1: 2-(2,5-dibromophenyl)-acetic acid With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 50℃; for 0.5h; Stage #2: 2-fluoro-5-(trifluoromethoxy)aniline at 50℃; for 16h;	132.A Step A: 2-(2,5-dibromophenyl)-N-(2-fluoro-5-(trifluoromethoxy)phenyl)acetamide To a stirred solution of 2-(2,5-dibromophenyl)acetic acid (1.00 g, 3.40 mmol) in pyridine (34.0 mL) was added HATU (1.36 g, 3.57 mmol), and the reaction mixture was allowed to stir at 50° C. for 30 minutes. 2-fluoro-5-(trifluoromethoxy)aniline (0.66 g, 3.40 mmol) was added via syringe, and the reaction mixture was allowed to stir at 50° C. for 16 h. The solvent was removed in vacuo. The residue was taken up in toluene, and the solvent was again removed in vacuo. The crude material was dry absorbed on SiO2 and subjected to flash silica gel column chromatography using a 0-40% EtOAc/hexanes gradient to afford the title compound. LC/MS=470 [M+1].
	Stage #1: 2-(2,5-dibromophenyl)-acetic acid With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 50℃; for 0.5h; Stage #2: 2-fluoro-5-(trifluoromethoxy)aniline at 50℃; for 16h;	132.A Step A: 2-(2,5-dibromophenyl)-N-(2-fluoro-5-(trifluoromethoxy)phenyl)acetamide To a stirred solution of 2-(2,5-dibromophenyl)acetic acid (1.00 g, 3.40 mmol) in pyridine (34.0 mL) was added HATU (1.36 g, 3.57 mmol), and the reaction mixture was allowed to stir at 50° C. for 30 minutes. 2-fluoro-5-(trifluoromethoxy)aniline (0.66 g, 3.40 mmol) was added via syringe, and the reaction mixture was allowed to stir at 50° C. for 16 h. The solvent was removed in vacuo. The residue was taken up in toluene, and the solvent was again removed in vacuo. The crude material was dry absorbed on SiO2 and subjected to flash silica gel column chromatography using a 0-40% EtOAc/hexanes gradient to afford the title compound. LC/MS=470 [M+1].

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2022/112181, 2022, A1
[2]Current Patent Assignee: MERCK & CO INC - US2022/112181, 2022, A1 Location in patent: Paragraph 0609; 0610
[3]Current Patent Assignee: MERCK & CO INC - US2022/112181, 2022, A1 Location in patent: Paragraph 0609; 0610

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