31181-84-7|(5-(Trifluoromethyl)pyridin-2-yl)methanol| Ambeed

Structure of 31181-84-7

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Quality Control of [ 31181-84-7 ] Purity: 96% SDS Specification

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Product Details of [ 31181-84-7 ]

CAS No. :	31181-84-7
Formula :	C₇H₆F₃NO
M.W :	177.12
SMILES Code :	OCC1=NC=C(C(F)(F)F)C=C1
MDL No. :	MFCD04117762
InChI Key :	GVAFEGOUIQFLQH-UHFFFAOYSA-N
Pubchem ID :	3820787

Safety of [ 31181-84-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 31181-84-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	35.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.5
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	0.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.59
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.	0.98
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	2.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.63

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.74
Solubility	3.25 mg/ml ; 0.0183 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.17
Solubility	12.0 mg/ml ; 0.0676 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.74
Solubility	0.324 mg/ml ; 0.00183 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	No
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.	-6.75 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)	1.76

Application In Synthesis of [ 31181-84-7 ]

* 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 [ 31181-84-7 ]
Downstream synthetic route of [ 31181-84-7 ]

[ 31181-84-7 ] Synthesis Path-Upstream 1~6

1
[ 124236-37-9 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 0 - 20℃;	IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of methyl 5-trifluoromethyl-pyridine-2-carboxylate (2 g, 9.75 mmol) in MeOH (30 mL) at 0°C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93percent yield): 1H NMR (400 MHz, CDC1₃) δ ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)⁺.
82.2%	at 0 - 20℃; for 1 h;	Compound SM (1.0 g, 4.87 mmol) was dissolved in MeOH (15 mL). At 0 ° C, NaBH4 (368.9 mg, 9.75 mmol) was added portionwise with stirring. Reaction at room temperature for 1 hour. TLC showed the reaction was completed. The pH was adjusted to 5-6 with 1 M HCl solution and the EA extracted (20 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (710.0 mg, 82.2percent).
72%	Stage #1: With sodium tetrahydroborate In ethanolHeating / reflux Stage #2: With water; ammonium chloride In ethanol at 20℃;	NaBH₄ (0.369 g, 9.75 mmol) was added to Example 34A (1 g, 5 mmol) in EtOH (40 mL). The suspension was heated at reflux overnight. The reaction was cooled to ambient temperature and quenched with saturated NH₄Cl solution. The mixture was diluted with water and extracted with EtOAc. The separated organic layer was washed with water and brine, dried (Na₂SO₄), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix.(R). 25*40 column, 30percent-50percent EtOAc/hexanes eluant) to afford 0.62 g (72percent) of the title compound as a colorless oil. ¹H NMR (300 MHz, CDCl₃) δ 8.84 (s, 1H), 7.94 (dd, J=8.3, 2.1 1H), 7.43 (dd, J=8.2, 0.6 1H), 4.85 (d, J=5.2, 2H), 3.46 (t, J=5.3, 1H).

References: [1] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 48.
[2] Patent: CN106831840, 2017, A, . Location in patent: Paragraph 0102; 0103; 0104.
[3] Patent: US2009/124666, 2009, A1, . Location in patent: Page/Page column 25-26.

2
[ 67-56-1 ]
[ 100366-75-4 ]
[ 31181-84-7 ]

References: [1] Patent: US2015/232460, 2015, A1, . Location in patent: Paragraph 0663-0666.

3
[ 541-41-3 ]
[ 80194-69-0 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
0.12 g	Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1 h;	A solution of 728 5-(trifluoromethyl)pyridine-2-carboxylic acid (0.19 g, 1.0 mmol) in 20tetrahydrofuran (10 mL) was cooled to 0° C., 14 triethylamine (0.18 mL, 1.3 mmol) and 126 ethylchloroformate (0.11 mL, 1.1 mmol) were added and the mixture was stirred for 10 min. The reaction mixturewas filtered, to the filtrate were added 49 sodium tetrahydroborate (49 mg, 1.3 mmol) and one piece of ice,and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added aqueous sodium hydroxidesolution and the mixture was stirred for 30 min, and extracted with dichloromethane. The organic layer waswashed with water, dried over sodium sulfate, and the desiccant was filtered off. The solvent was evaporatedto give the 729 title compound as a crudely purified product (0.12 g) MS (ESI) m/z 178 (M+H)+

References: [1] Patent: US2016/332999, 2016, A1, . Location in patent: Paragraph 0890; 0891.

4
[ 31224-82-5 ]
[ 31181-84-7 ]

References: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6563 - 6585.

5
[ 100366-75-4 ]
[ 31181-84-7 ]

References: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6563 - 6585.

6
[ 50488-42-1 ]
[ 31181-84-7 ]

References: [1] Patent: WO2013/166621, 2013, A1, .

[ 31181-84-7 ] Synthesis Path-Downstream 1~35

1
[ 856245-58-4 ]
[ 31181-84-7 ]
7,8-bis(4-chlorophenyl)-2-((5-(trifluoromethyl)pyridin-2-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20℃; for 0.5h;	To a solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (100 mg, 0.28 mmol), prepared as described in Example 1, Ph3P (220 mg, 0.84 mmol) and <strong>[31181-84-7](5-trifluoromethyl-pyridin-2-yl)methanol</strong> (50 mg, 0.28 mmol) in THF (2.0 mL) was added 40 wt % diethyl azodicarboxylate (DEAD) solution in toluene (0.33 mL, 0.84 mmol) at RT under argon. The reaction was stirred at RT for 30 min. Water (5.0 mL) was then added and the resulting mixture was extracted with EtOAc (3×5 mL). The combined organic layers were washed with water (2×5 mL) followed by saturated aqueous NaCl (2×5 mL). The combined organic layers were concentrated under reduced pressure to obtain the crude product. This crude product was purified using reverse phase preparative HPLC to give the title compound 7,8-bis(4-chlorophenyl)-2-((5-(trifluoromethyl)pyridin-2-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (69.2 mg, 48%) as a yellow solid. MS (M+H)=516; 1H NMR (CDCl3): delta 8.83 (1H, s), 8.20 (1H, s), 7.93 (1H, d, J=8.2 Hz), 7.40 (1H, d, J=10.0 Hz), 7.26-7.34 (6H, m), 7.11 (2H, d, J=10.0 Hz), 5.47 (2H, s).

References: [1]Patent: US2005/143381,2005,A1 .Location in patent: Page/Page column 16.

2
[ 31181-84-7 ]
[ 31224-82-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 0.333333h;	A solution of Example 34B (3.89 g, 22.0 mmol) in CH2Cl2 (10 mL) was added to a deoxygenated solution of Dess-Martin periodinane (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one, 10.3 g, 24.2 mmol) in CH2Cl2 (73 mL) in one portion. The reaction was stirred under nitrogen at ambient temperature for about 20 minutes after which a solid formed. The reaction was diluted with 50 mL CH2Cl2 and carefully quenched with approximately 30 mL of saturated NaHCO3 solution. The undissolved solid was filtered, and the filtrate was transferred to a separatory funnel. The aqueous phase was extracted with CH2Cl2, and the combined organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated at reduced pressure to 50 mL. This solution was then loaded on silica gel (Analogix 40*150 column) and eluted with 25% to 50% EtOAc/hexanes. The result was 2.86 g (74%) of the title compound as a clear oil, which solidified on standing. 1H NMR (300 MHz, CDCl3) delta 10.15 (s, 1H), 9.06 (m, 1H), 8.15 (m, 1H), 8.09 (d, J=8.1, 1H).
	With manganese(IV) oxide; In chloroform; at 20℃; for 15h;Heating / reflux;	EXAMPLE 18; trans-N-[4-(4,5-Dichloro-imidazol-1-yl)-3-trifluoromethyl-phenyl]-3-(5-trifluoromethyl-pyridin-2-yl)-acrylamide (Cpd 235) A. To a solution of compound 18a (3.84 g, 21.7 mmol), in 25 mL CHCl3 was added manganese dioxide (MnO2) (8.04 g). After stirring at ambient temperature for 15 hours the suspension was heated at reflux under a nitrogen atmosphere for an additional 23 hours. The reaction mixture was filtered over a pad of celite and the filter cake washed with additional CHCl3. The filtrate was evaporated in vacuo to yield the product, compound 18b as an orange oil. MS: M+H+=175.8, 1H NMR (CDCl3): delta 10.15 (s, 1H), 9.06 (s, 1H), 8.17-8.06 (m, 2H).
		Intermediate 13: 2-[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine Step (i): 5-(Trifluoromethyl)pyridine-2-carbaldehyde Dess-Martin periodinane (CAS number 87413-09-0; 13.17 g, 31.10 mmol) was added to a solution of <strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (CAS number 31181-84-7; 5.00 g, 28.2 mmol) in DCM (60 ml). The reaction was stirred at room temperature for 18 hours and then a saturated solution of sodium thiosulfate (aq, 100 ml) was added. The reaction was stirred for 45 min at room temperature and then phases separated. The aqueous phase was further extracted with DCM (60 ml) and the combined organics were washed with a saturated solution of sodium bicarbonate (aq, 60 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound. MS ES+: 176

References: [1]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 26.
[2]Patent: US2006/223837,2006,A1 .Location in patent: Page/Page column 35.
[3]Patent: US2015/232460,2015,A1 .Location in patent: Paragraph 0478-0480.

3
[ 31181-84-7 ]
[ 1000773-62-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With phosphorus tribromide; In dichloromethane; at 0 - 20℃;	To an ice-cooled solution of (5-trifluoromethyl-pyridin-2-yl)-methanol (300 mg, 1.69 mmol) inDCM (10 mL) is added phosphoros tribromide (96 mul_, 1.02 mmol) and the reaction mixture is stirred for 2 h at room temperature. The reaction mixture is quenched with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated under reduced pressure.Yield: 350 mg (86% of theory); ESI Mass spectrum: [M+H]+ = 239Retention time HPLC: 1.37 min (method J).
77%	With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; for 3h;	2-(bromomethyl)-5-(trifluoromethyl)pyridine<strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (2.Og, 11.29 mmol) was dissolved in DCM (20 ml_) at r.t. Imidazole (824 mg, 11.9 mmol) was added and allowed to dissolve. Triphenylphosphine (3.36 g, 12.4 mmol) was then added and dissolved. Bromine (0.58 ml_, 11.3 mmol) was added last and stirred for 3 hours. The reaction was quenched water and extracted with dichloromethane (2x 25 ml_). The organics were dried with magnesium sulfate and concentrated. The crude product was purified by flash chromatography (heptanes:ethyl acetate) to give the title compound as a clear liquid (2.1 g, 8.75 mmol, 77%).
		Reference Production Example 2. In 70 mL of tetrahydrofuran, 4.44 g of (5- trifluoromethylpyridin-2-yl) methanol was dissolved and 1.9 mL of methanesulfonyl chloride and 3.5 mL of triethylamine were added dropwise at 00C. After stirring at the same temperature for 0.5 hours, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was dissolved in 30 mL of N, N-dimethylformamide. To the solution was added 4.4 g of lithium bromide at room temperature. The reaction mixture was heated to 90C and, after stirring for 10 minutes and returning to room temperature, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was subjected to column chromatography to obtain 1.68 g of 2- bromomethyl-5-trifluoromethylpyridine.1H-NMR (CDCl3, TMS) : delta (ppm) 8.84 (IH, s), 7.94 (IH, dd) ,7.59 (IH, d) , 4,59 (2H, s).

	With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 3h;	Step (ii): 2-(Bromomethyl)-5-(trifluoromethyl)pyridine To a solution of <strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (5.0 g, 28.24 mmol) in DCM (50 ml) was added tribromophosphane (0.58 g, 3.50 mmol) at 0 C. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction was then poured into water (50 ml) and the organics were extracted with DCM (2×50 ml), washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound which was used without further purification. MS ES+: 240, 242
	With phosphorus tribromide; In dichloromethane; at 20℃; for 3h;	Intermediate 1 (390.0 mg, 2.2 mmol) was dissolved in DCM (10 mL). 0 C, a solution of PBr3 (387.0 mg, 1.43 mmol) in DCM (2 mL) was added dropwise. The reaction was carried out for 3 hours at room temperature. TLC showed the reaction was completed. The pH was adjusted to 6-7 with saturated NaHCO3 solution, H2O (15 mL) added and DCM extracted (15 mLx3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (450.0 mg, 80.0% purity, 68.1% yield).

References: [1]Patent: WO2009/103478,2009,A1 .Location in patent: Page/Page column 51.
[2]Patent: WO2010/58318,2010,A1 .Location in patent: Page/Page column 78.
[3]Patent: WO2009/25397,2009,A1 .Location in patent: Page/Page column 161-162.
[4]Patent: US2015/232460,2015,A1 .Location in patent: Paragraph 0667-0668.
[5]Patent: CN106831840,2017,A .Location in patent: Paragraph 0105; 0106; 0107.

4
[ 31181-84-7 ]
[ 1301167-65-6 ]
[ 1301168-19-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5820 - 5835.

5
[ 31224-82-5 ]
[ 31181-84-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6563 - 6585.

6
[ 31181-84-7 ]
[ 1333170-17-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6563 - 6585.

7
[ 31181-84-7 ]
[ 128790-14-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6563 - 6585.

8
[ 100366-75-4 ]
[ 31181-84-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6563 - 6585.

9
[ 50488-42-1 ]
[ 31181-84-7 ]