1227594-89-9|3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one| Ambeed

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Quality Control of [ 1227594-89-9 ] Purity: 97% SDS Specification

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Product Details of [ 1227594-89-9 ]

CAS No. :	1227594-89-9
Formula :	C₆H₃F₄NO
M.W :	181.09
SMILES Code :	O=C1C(F)=C(C(F)(F)F)C=CN1
MDL No. :	MFCD26405803
InChI Key :	CUVQCPUTFJFSFU-UHFFFAOYSA-N
Pubchem ID :	53435090

Safety of [ 1227594-89-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 1227594-89-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	32.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.23
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	0.95
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.11
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.	1.81
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	2.97
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.87
Solubility	2.47 mg/ml ; 0.0136 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.	-1.23
Solubility	10.7 mg/ml ; 0.0593 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	-3.1
Solubility	0.145 mg/ml ; 0.0008 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.	-6.73 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)	1.8

Application In Synthesis of [ 1227594-89-9 ]

* 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.

Downstream synthetic route of [ 1227594-89-9 ]

[ 1227594-89-9 ] Synthesis Path-Downstream 1~26

1
[ 113770-87-9 ]
[ 1227594-89-9 ]

References: [1]Patent: US2011/245296,2011,A1 .

2
3-fluoro-4-(trifluoromethyl)pyridine 1-oxide [ No CAS ]
[ 1227594-89-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step 8(d): 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (8-5) A solution of 3-fluoro-4-(trifluoromethyl)pyridine (5.00 g; 30.3 mmol) in CH2Cl2 (10 mL) was cooled to 0 C., then methyltrioxorhenium(VII) (0.062 g; 0.249 mmol) and hydrogen peroxide (30%; 6.2 mL; 61 mmol) were added and the mixture was warmed to room temperature. After stirring for 2 hours, the reaction was quenched by the addition of MnO2 (5 mg) and 30 minutes additional stirring. After dilution with additional CH2Cl2, the mixture was filtered through Solka Floe, dried (MgSO4) and concentrated in vacuo to provide 3-fluoro-4-(trifluoromethyl)pyridine 1-oxide of sufficient purity to be used directly. The N-oxide (3.70 g; 20.4 mmol) was dissolved in trifluoroacetic anhydride (21.6 mL; 153 mmol) in a hydrogenation bomb and heated to 85 C. for 15 hours. After cooling to 0 C., water was added, followed by solid K2CO3 until pH 9. The aqueous fraction was extracted with EtOAc and Me-THF, and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash (70:30 to 0:100 hexanes:EtOAc) provided the title compound as a pink solid. 1H NMR (400 MHz, Acetone): delta 11.48 (s, 1 H); 7.55 (d, J=7.1 Hz, 1 H); 6.39 (t, J=6.2 Hz, 1H).

References: [1]Patent: US2011/245296,2011,A1 .Location in patent: Page/Page column 26.

3
[ 1338226-21-3 ]
[ 1227594-89-9 ]
[ 1338226-22-4 ]

Yield	Reaction Conditions	Operation in experiment
		Step 8(f): 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8) To a solution of <strong>[1227594-89-9]3-fluoro-4-(trifluoromethyl)pyridin-2-ol</strong> (8-5; 50 mg; 0.34 mmol) in dioxane 1.7 mL) was added K2CO3 (51 mg; 0.373 mmol) and the mixture was stirred for 5minutes. 5-(chloromethyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (8-4; 68 mg; 0.373 mmol) was then added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with water, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash provided the title compound. 1H NMR (400 MHz, CDCl3): delta 10.14 (s, 1 H); 8.11 (d, J=5.2 Hz, 1 H); 7.18 (t, J=4.7 Hz, 1 H); 5.40 (s, 2 H); 3.41 (s, 3 H).

References: [1]Patent: US2011/245296,2011,A1 .Location in patent: Page/Page column 26.

4
[ 1227594-89-9 ]
[ 1613307-23-5 ]
[ 1613307-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	A mixture of 2 (100 mg, 93.1% purity, 0.49 mmol), pyridone (1 17 mg, 97.6% purity, 0.49 mmol) and K2CO3 (82 mg, 0.59 mmol) in DMF (0.5 ml) was aged with stirring at ambient temperature for 3h. After the reaction was completed, the batch was taken on to the next step without further work up or isolation.

References: [1]Patent: WO2014/89140,2014,A1 .Location in patent: Page/Page column 17; 18.

5
[ 1227594-89-9 ]
tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate [ No CAS ]
[ 76-05-1 ]
N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.2 mg		[00542] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (30 mg, 0.07 mmol) was dissolved in THF (0.5 mL). 6-hydroxy-2-methylpyridazin-3(2H)-one (26 mg, 0.21 mmol) and PPh3 (55 mg, 0.21 mmol) were added, followed by DIAD (0.041 mL, 0.21 mmol). The reaction mixture was stirred overnight and then concentrated. The residue was dissolved in DCM (1 mL) and 4N HCl in dioxane (1 mL) was added and stirred for 2 h. The reaction mixture was concentrated and the residue purified on C-18 silica column (5 to 95% ACN in water with 0.1% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20% yield). Mass spectrum (apci) m/z = 436.2 (M+H).1H NMR (CD3OD) delta 9.05 (s, 1H), 8.15 (s, 1H), 7.47 (s, 1H), 7.28 (d, J = 9.6 Hz, 1H), 7.00 (d, J = 9.6 Hz, 1H), 6.97 (s, 1H), 5.16 (m, 1H), 4.75 (m, 1H), 3.65 (s, 3H), 3.45 (q, J = 7.2 Hz, 2H), 2.50-2.31 (m, 4H), 1.99-1.86 (m, 4H), 1.38 (t, J = 7.2 Hz, 3H).

References: [1]Patent: WO2019/113190,2019,A1 .Location in patent: Paragraph 00542.

6
[ 1227594-89-9 ]
tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate [ No CAS ]
N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.2 mg	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;	[00647] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (50 mg, 0.12 mmol) was dissolved in THF (1 mL) and <strong>[1227594-89-9]3-fluoro-4-(trifluoromethyl)pyridin-2-ol</strong> (63.5 mg, 0.35 mmol) and PPh3 (92 mg, 0.35 mmol) were added, followed by DIAD (0.069 mL, 0.35 mmol) and stirred overnight. The reaction mixture was concentrated and dissolved in DCM (1 mL) and 4M HCl in dioxane (2 mL) was added. After 2 h, the reaction was concentrated and purified by preparative HPLC (5 to 95% ACN in water with 0.2% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20.5% yield). Mass spectrum (apci) m/z = 491.1 (M+H). 1H NMR (CD3OD) delta 9.05 (d, J = 0.8 Hz, 1H), 8.14 (m, 2H), 7.46 (d, J = 0.8 Hz, 1H), 7.20 (t, J = 4.7 Hz, 1H), 6.92 (s, 1H), 5.55 (m, 1H), 4.77 (m, 1H), 3.44 (q, J = 7.0 Hz, 2H), 2.51 (m, 2H), 2.36 (m, 2H), 2.05-1.95 (m, 4H), 1.38 (t, J = 7.0 Hz, 3H).

References: [1]Patent: WO2019/113190,2019,A1 .Location in patent: Paragraph 00647.

7
[ 1227594-89-9 ]
(1r,4r)-4-(6-(ethylamino)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexan-1-ol [ No CAS ]
N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25.8%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;	[00643] Step C: (1r,4r)-4-(6-(ethylamino)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexan-1-ol (0.0101 g, 0.0296 mmol), <strong>[1227594-89-9]3-fluoro-4-(trifluoromethyl)pyridin-2-ol</strong> (0.0161 g, 0.0887 mmol), PPh3 (0.0233 g, 0.0887 mmol) were dissolved in THF (0.5 mL) and then DIAD (0.0179 g, 0.0887 mmol) was added and stirred overnight and then concentrated. The residue was purified over preparative HPLC (5-95% ACN in water with 0.2% TFA) and concentrated to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (5.6 mg, 25.8 % yield). Mass spectrum (apci) m/z = 505.2 (M+H).1H NMR (CD3OD) delta 8.91 (s, 1H), 8.13 (d, 1H), 7.70 (s, 1H), 7.20 (m, 1H), 6.82 (s, 1H), 5.53 (s, 1H), 4.99 (m, 1H), 4.70 (m, 1H), 3.42 (q, J = 7.0 Hz, 2H), 2.61 (s, 3H), 2.53-2.30 (m, 4H), 1.96 (m, 4H), 1.36 (t, J = 7.0 Hz, 3H).

References: [1]Patent: WO2019/113190,2019,A1 .Location in patent: Paragraph 00643.

8
[ 1227594-89-9 ]
tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1r,4S)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate [ No CAS ]
tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1s,4R)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;	[00778] Step C: A solution of triphenylphosphine (39 mg, 0.149 mmol) in THF (1 mL) at room temperature was treated with DIAD (29 muL, 0.149 mmol). The mixture was stirred for 10 min and then tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1r,4S)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (50.9 mg, 0.099 mmol) was added in THF (1 mL), followed by <strong>[1227594-89-9]3-fluoro-4-(trifluoromethyl)pyridin-2-ol</strong> (36 mg, 0.199 mmol). The mixture stirred overnight and partitioned between water (15 mL) and EtOAc (10 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silca gel (20-70% EtOAc in hexanes) to afford tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1s,4R)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (77.7 mg, 115% yield).

References: [1]Patent: WO2019/113190,2019,A1 .Location in patent: Paragraph 00778.

9
[ 1227594-89-9 ]
tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate [ No CAS ]
tert-butyl (3-bromo-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;	[00602] Step A: A solution of triphenylphosphine (1.34 g, 5.1 mmol) in THF (25 mL) was cooled to 0 C and treated with DIAD (1.0 mL, 5.12 mmol). The mixture was stirred for 15 min, then tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.5 g, 3.41 mmol) was added as a solid, followed by a solution of <strong>[1227594-89-9]3-fluoro-4-(trifluoromethyl)pyridin-2-ol</strong> (1.24 g, 6.83 mmol) in THF (10 mL) over 5 min. The mixture was allowed to warm slowly to room temperature overnight. The mixture was partitioned between water (100 mL) and EtOAc (100 mL) and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (10-40% EtOAc/hexanes) to afford tert-butyl (3-bromo-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.07 g, 52 % yield).

References: [1]Patent: WO2019/113190,2019,A1 .Location in patent: Paragraph 00602; 00605; 00614.

10
[ 1227594-89-9 ]
(R)-3-(4-(6-(ethylamino)-1-((1s,4S)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-3-yl)-1H-pyrazol-1-yl)propane-1,2-diol [ No CAS ]