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[ CAS No. 1201187-18-9 ]

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2D 3D

Chemical Structure| 1201187-18-9

Chemical Structure| 1201187-18-9

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Quality Control of [ 1201187-18-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1201187-18-9 ]

SDS Specification

Alternatived Products of [ 1201187-18-9 ]

Product Details of [ 1201187-18-9 ]

CAS No. :	1201187-18-9	MDL No. :	MFCD15528775
Formula :	C₇H₂ClF₃N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MXQLUANSPBCUGU-UHFFFAOYSA-N
M.W :	206.55 g/mol	Pubchem ID :	58009884
Synonyms :

Calculated chemistry of [ 1201187-18-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.96
TPSA :	36.68 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) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	2.42
Log Po/w (WLOGP) :	3.78
Log Po/w (MLOGP) :	1.47
Log Po/w (SILICOS-IT) :	2.99
Consensus Log Po/w :	2.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.92
Solubility :	0.248 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.304 mg/ml ; 0.00147 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.0495 mg/ml ; 0.00024 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.99

Safety of [ 1201187-18-9 ]

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

Application In Synthesis of [ 1201187-18-9 ]

* 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 [ 1201187-18-9 ]
Downstream synthetic route of [ 1201187-18-9 ]

[ 1201187-18-9 ] Synthesis Path-Upstream 1~1

1
[ 287922-66-1 ]
[ 896447-72-6 ]
[ 1201187-18-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	at 110℃; for 5 h;	Intermediate 6; 2-chloro-4-(trifluoromethyl)nicotinonitrile; A mixture of 4-(trifluoromethyl)nicotinonitrile 1-oxide (10.5 g, 55.8 mmol) and POCl₃ (51 mL, 558 mmol) was heated at 110 °C for 5 hours. After evaporation of excess POCl₃, the residue was taken up in dichloromethane and washed successively with 5percent K₂CO₃ and water. The organic phase was then dried over Na₂SO₄, filtered and concentrated to give a mixture of the title compound and 6-chloro-4-(trifluoromethyl)nicotinonitrile. ¹H NMR analysis of the crude material showed that the title compound was the major isomer (7:3 2- EPO <DP n="38"/>chloro:6-chloro). The isomers were separated by flash chromatography. The 6-chloro isomer was eluted first with 9:1 hexanes:Et₃N. Eluting with dichloromethane gave the title compound as an orange oil (4.50 g, 38percent).

Reference： [1] Patent: WO2006/68618, 2006, A1, . Location in patent: Page/Page column 36-37

[ 1201187-18-9 ] Synthesis Path-Downstream 1~4

1
[ 287922-66-1 ]
[ 896447-72-6 ]
[ 1201187-18-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	With trichlorophosphate; at 110℃; for 5.0h;	Intermediate 6; 2-chloro-4-(trifluoromethyl)nicotinonitrile; A mixture of 4-(trifluoromethyl)nicotinonitrile 1-oxide (10.5 g, 55.8 mmol) and POCl3 (51 mL, 558 mmol) was heated at 110 C for 5 hours. After evaporation of excess POCl3, the residue was taken up in dichloromethane and washed successively with 5% K2CO3 and water. The organic phase was then dried over Na2SO4, filtered and concentrated to give a mixture of the title compound and 6-chloro-4-(trifluoromethyl)nicotinonitrile. 1H NMR analysis of the crude material showed that the title compound was the major isomer (7:3 2- EPO <DP n="38"/>chloro:6-chloro). The isomers were separated by flash chromatography. The 6-chloro isomer was eluted first with 9:1 hexanes:Et3N. Eluting with dichloromethane gave the title compound as an orange oil (4.50 g, 38%).

Reference： [1]Patent: WO2006/68618,2006,A1 .Location in patent: Page/Page column 36-37

2
[ 1201187-18-9 ]
4-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridine-6-one hydrochloride [ No CAS ]
6-{4-[4-hydroxy-6-oxo-4-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridine-3-yl]piperidin-1-yl}-4-(trifluoromethyl)pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 0.333333h;Microwave irradiation;	4-hydroxy was prepared in Reference Example 60 3- (piperidin-4-yl) -4- (trifluoromethyl) -1,4,5,7- tetrahydro -6H- pyrazolo [3,4-b] pyridin-6-one hydrochloride (150mg, 0.440mmol) in dimethyl sulfoxide (0.5 mL) solution of, N, N- diisopropylethylamine (89.8muL, 0.528mmol), and 6-fluoro-3- ( the compounds described in trifluoromethyl) pyridine-2-carbonitrile (US2008 / 275057 pamphlet, 136mg, 0.660mmol) was added, using a Biotage Inc. the Initiator (TM), 60 C., 20 min micro and the mixture was stirred while irradiating the waves.The reaction mixture was poured into water, and extracted twice with ethyl acetate, the resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatography was purified in the elution solvent hexane / ethyl acetate = 88 / 12-0 / 10 gradient)], the title compound (43.1mg, yield: 21%) a.

Reference： [1]Patent: JP2015/113323,2015,A .Location in patent: Paragraph 0727 - 0729; 0730 - 0732

3
[ 1201187-18-9 ]
[ 35344-95-7 ]
6-(4-formyl-1H-pyrazol-1-yl)-4-(trifluoromethyl)nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.10%	With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; In 1,4-dioxane; at 110℃; for 1h;Inert atmosphere; Microwave irradiation;	General procedure: To a stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N'dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 °C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040percent EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10percent) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

Reference： [1]Patent: WO2018/222795,2018,A1 .Location in patent: Page/Page column 63; 64; 236

4
[ 1201187-18-9 ]
4-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridine-6-one hydrochloride [ No CAS ]
[ 76-05-1 ]
6-(4-(4-hydroxy-6-oxo-4-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1-yl)-4-(trifluoromethyl)nicotinonitrile trifluoroacetate [ No CAS ]

Reference： [1]eLife,2018,vol. 7

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Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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Code	Phrase
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere