1196155-38-0|2-Chloro-6-(trifluoromethyl)isonicotinonitrile| Ambeed

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Quality Control of [ 1196155-38-0 ] Purity: 95% SDS Specification

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Product Details of [ 1196155-38-0 ]

CAS No. :	1196155-38-0
Formula :	C₇H₂ClF₃N₂
M.W :	206.55
SMILES Code :	N#CC1=CC(C(F)(F)F)=NC(Cl)=C1
MDL No. :	MFCD13190042
InChI Key :	DKJFUZIDAHUIJV-UHFFFAOYSA-N
Pubchem ID :	53407604

Safety of [ 1196155-38-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 1196155-38-0 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.69
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	2.45
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.78
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.	1.47
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	2.99
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.94
Solubility	0.237 mg/ml ; 0.00115 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.	-2.86
Solubility	0.283 mg/ml ; 0.00137 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	-3.62
Solubility	0.0495 mg/ml ; 0.00024 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.	-5.82 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	0.0
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)	1.94

Application In Synthesis of [ 1196155-38-0 ]

* 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 [ 1196155-38-0 ]

[ 1196155-38-0 ] Synthesis Path-Downstream 1~35

1
[ 1196155-38-0 ]
[ 67-63-0 ]
[ 1333153-74-4 ]

Yield	Reaction Conditions	Operation in experiment
		In a 250-mL 3 neck round-bottomed flask flask NaH (1.39 g) suspended in THF (100 mL) at 0°C. Isopropanol (4.36 g)was added to the above reaction mixture. Reaction mixture was allowed to stirred at RT for 3 h and 2-chloro-6- trifluoromethylisonicotinonitrile(lOg) in THF(80 mL) was added dropwise at 0°C. Reaction mixture was maintained 0°C for 30 min. Completion of reaction was monitored by TLC. Reaction mixture was quenched in ice water slurry. Compound was extracted in ethylacetate and organic layer was washed with water (100 mL x2) dried over anhydrous N3/4S04, filtered, and concentrated under reduced pressure (40°C, 20mmHg) to afford 8g of a yellow oil. The resulting crude compound forwarded for next step.
		Synthesis -isopropoxy-6-(trifluoromethyl)isonicotinonitrile:[00338] In a 250-ml capacity 3 neck flask (1.39g) NaH suspended in 100 ml THF. At 0 °C IPA (4.36g) in 20 ml THF added in this reaction flask. Allow it to stirr at RT for 3h. At 0 °C <strong>[1196155-38-0]2-chloro-6-trifluoromethylisonicotinonitrile</strong> (10 g) in 80 mL THF added in the flask in dropwise manner. Maintained 0 °C temperature for 30 min. Completion of reaction conformed by TLC. Reaction mixture was dumped in ice water. Extract compound in ethyl acetate. Organic layer was washed by water two times dried over Na2S04, filtered, and concentrated by rotary evaporation (40 °C, 20 mmHg) to afford 8 g of yellow oil. The resulting crude compound forwarded for next step.

References: [1]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 232-233.
[2]Patent: WO2012/99807,2012,A1 .Location in patent: Page/Page column 93-94.

2
[ 2516-34-9 ]
[ 1196155-38-0 ]
[ 1333153-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	hydrogenchloride; In butan-1-ol; at 130℃; for 0.5h;Microwave;	Synthesis of Intermediate (1) 1.21[00654] In a25-mL microwave seal tube <strong>[1196155-38-0]2-chloro-6-trifluoromethylisonicotinonitrile</strong> (lg) Isopropyl amine(0.517g) was dissolved in n-butanol(lOmL) and one drop of con. HC1 was added. Reaction mixture was irradiated at 130°C for 30 min in Microwave. The Completion of the reaction was confirmed by TLC using 10percent EtOAc-n-hexane as mobile phase. Reaction mixture was quenched into ice water slurry. Extract compound in ethyl acetate, organic layer washed with water two times dried over Nu3/4804, filtered, and concentrated by rotary evaporation(40°C,20 mmHg) to afford 8g of a yellow oil. The resulting crude compound was purified by column chromatography. The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate :n-hexane as mobile phase. The columnwas packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection(25 -mL fractions) from 1-3 percent ethyl acetate in hexane. Compound started eluting with 2 percent ethylacetate in hexane. Fraction containing such TLC profile was collected together to obtain pure compound(0.8 g).

References: [1]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 249-250.

3
[ 1196155-38-0 ]
[ 75-31-0 ]
[ 1333153-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	hydrogenchloride; In butan-1-ol; at 130℃; for 0.5h;microwave radiation;	Synthesi f Intermediat 1)Molecular Weight: 206.55 Molecular Weight: 229.20[00644] In a 25-mL capacity microwave seal tube 2-chloro-6- trifluoromethylisonicotinonitrile(lg) Isopropyl amine(0.571g) dissolved in n-Butanol(10 mL) with one drop of Con HCl. Reaction mixturure was irradiated with microwave radiation at 130°C for 30 min in 150 Watt. The Completion of the reaction was confirmed by TLC with 10percent EtOAc- n-hexane as mobile phase. Reaction mixture was quenched into ice water slurry. Compound was extracted in ethyl acetate(100 mLx2) and organic layer washed with water(100 mL x 2) dried over Na2S04,filtered, and concentrated under reduced by rotary evaporation (40°C,20mmHg) to afford 8g of a yellow oil. The resulting crude compound was used as such without any further purification.[00645] The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate: hexane as mobile phase. The columnwas packed in hexane and started eluting in ethyl acetate in gradient manner starting with fractioncollection(25- mLfractions) from 1 percent to 3 percent ethyl acetate in hexane. Compound started eluting with 2 percent ethylacetate in hexane. Fractions containing such TLC profile was collected together to obtain pure compound (0.8 g).

References: [1]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 246-247.

4
[ 1196155-38-0 ]
[ 1333153-75-5 ]

References: [1]Patent: WO2011/109799,2011,A1 .
[2]Patent: WO2012/99807,2012,A1 .

5
[ 1196155-38-0 ]
[ 1333153-76-6 ]

References: [1]Patent: WO2011/109799,2011,A1 .
[2]Patent: WO2012/99807,2012,A1 .

6
[ 1196155-38-0 ]
[ 1333153-77-7 ]

References: [1]Patent: WO2011/109799,2011,A1 .
[2]Patent: WO2012/99807,2012,A1 .

7
[ 1196155-38-0 ]
C₁₁H₁₃F₃N₄O₂ [ No CAS ]