31872-62-5|4-Methoxy-3-nitropyridine| Ambeed

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Quality Control of [ 31872-62-5 ] Purity: 98% SDS Specification

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Product Details of [ 31872-62-5 ]

CAS No. :	31872-62-5
Formula :	C₆H₆N₂O₃
M.W :	154.12
SMILES Code :	COC1=C(C=NC=C1)[N+](=O)[O-]
MDL No. :	MFCD00209661
InChI Key :	BZPVREXVOZITPF-UHFFFAOYSA-N
Pubchem ID :	355832

Safety of [ 31872-62-5 ]

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

Computational Chemistry of [ 31872-62-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	39.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.01
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	0.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.0
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.	-0.96
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	-0.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.48
Solubility	5.14 mg/ml ; 0.0334 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.	-1.65
Solubility	3.43 mg/ml ; 0.0223 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	-1.52
Solubility	4.68 mg/ml ; 0.0303 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	No
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.	-6.78 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	2.0 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)	2.0

Application In Synthesis of [ 31872-62-5 ]

* 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 [ 31872-62-5 ]

[ 31872-62-5 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 13091-23-1 ]
[ 31872-62-5 ]

References: [1]Justus Liebigs Annalen der Chemie,1937,vol. 529,p. 291.
[2]Chemische Berichte,1942,vol. 75,p. 1936,1942.
[3]Organic Letters,2000,vol. 2,p. 2253 - 2256.

2
[ 124-41-4 ]
[ 13091-23-1 ]
[ 31872-62-5 ]

References: [1],1934,vol. 2,p. 384,387.

3
[ 107-10-8 ]
[ 31872-62-5 ]
[ 438554-27-9 ]

References: [1]Chemische Berichte,1942,vol. 75,p. 1936,1942.

4
[ 996-82-7 ]
[ 31872-62-5 ]
[ 54415-82-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1937,vol. 529,p. 291.

5
[ 31872-62-5 ]
[ 107-21-1 ]
2-((3-nitropyridin-4-yl)oxy)ethanol [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1936,vol. 521,p. 286,293.

6
[ 31872-62-5 ]
[ 109-73-9 ]
[ 120759-78-6 ]

References: [1]Chemische Berichte,1942,vol. 75,p. 1936,1942.

7
[ 31872-62-5 ]
[ 77-78-1 ]
[ 100725-07-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1958,vol. 617,p. 181,202.

8
[ 31872-62-5 ]
[ 95-53-4 ]
(3-nitro-[4]pyridyl)-o-tolyl-amine [ No CAS ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1181,1183,1186.

9
[ 31872-62-5 ]
[ 33631-09-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr; for 6h;	EXAMPLE 93; Synthesis of 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amide; Step 1: To a mixture of <strong>[31872-62-5]4-Methoxy-3-nitropyridine</strong> (5.0 g, 32.44 mmole) in ethanol (100 mL) was added 10 % palladium on carbon catalyst (200 mg). The resulting mixture was allowed to shake under a hydrogen atmosphere (50 psi) for 6 h. at room temperature. TLC (50% ethyl acetate/hexane) indicated complete consumption of starting material. Filtration through celite to remove the catalyst and concentration gave 3-Amino4 methoxypyridine (4.0 g, 32.44 mmol, 100% yield) as dark red oil.
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2585.81 Torr;	Step 1: 4-methoxypyridin-3-amineA solution of 4-methoxy -3-nitropyridine (100 g, 0.65 mol, Ouhe) and 10% Pd/C (10 g) in MeOH (2 L) was stirred under 50 psi of hydrogen. The reaction mixture was stirred at rt overnight. The mixture was filtered and concentrated in vacuo to afford 4-methoxypyridin-3- amine (82.1 g, quantitative) as a yellow solid.
99%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 48h;	Example 26Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(4-methoxy-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.475 g (3.08 mmol) of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (Org. Process Res. Dev. 2004, 8, 903-908) and 0.301 g (2.84 mmol) of 10% palladium on carbon in ethanol (30 mL) was stirred under an atmosphere of hydrogen for 48 hrs. The catalyst was removed by filtration through a pad of celite, and the solvent was removed to give 0.380 mg (99%) of 3-amino-4-methoxypyridine as a pink powder, which was used in the next step without further purification: 1H NMR (DMSO-d6) delta8.09 (dd, J=6.4, 1.2 Hz, 1H), 7.93 (d, J=1.2 Hz, 1H), 7.36 (d, J=6.4 Hz, 1H), 6.01 (br s, 2H), 4.06 (s, 3H).To a solution of 0.134 g (1.08 mmol) of 3-amino-4-methoxypyridine in THF (3 mL) was added 0.5 mL of butyllithium (2.5 M solution in hexanes), and the mixture was stirred for 15 min. A solution of 0.133 g (0.36 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole in THF (6 mL) was added and the resulting mixture was stirred for 1 hr. After neutralization with acetic acid, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed sequentially with water and aq. NH3, dried, and concentrated. Chromatography on alumina, eluting first with hexanes/EtOAc (1:1) and then with CH2Cl2/EtOAc (2:3) gave a white powder. Recrystallization from ethanol/CH2Cl2 gave 0.078 g (48% yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(4-methoxy-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 161-163 C.; 1H NMR (DMSO-d6) delta9.43 (br s, 1H), 8.61-8.37 (m, 3H), 7.83-7.81 (m, 2H), 7.41 (br s, 2H), 7.20 (d, J=5.6 Hz, 1H), 3.89 (s, 3H), 3.81 (s, 4H), 3.71 (s, 4H); Anal. Calcd. for C21H20F2N8O2: C, 55.5; H, 4.4; N, 24.7. Found: C, 55.5; H, 4.4; N, 24.5%.

44%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 760.051 Torr; for 10h;	To a solution of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (2.5 g, 16.2 mmol) in MeOH (50 mL) was added Pd/C 10% wt/wt (0.5 g) and the mixture was stirred under 1 atm H2 for 10 hours at room temperature. The reaction mixture was filtered through celite and filtrate was concentrated. The crude residue was purified by flash chromatography (0-10% MeOH/CH2Cl2) to give compound 16 (0.875 g, 44%). 1H NMR (400 MHz, DMSO-D6) delta 7.83 (s, 1H) 7.70 (d, 1H) 6.79 (d, 1H) 4.79 (s, 2H) 3.79 (s, 3H).
	With hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; for 5h;	A mixture of <strong>[31872-62-5]4-methoxy-3-nitro-pyridine</strong> (19.2 g, 0.13 mol) and Pd/C (10%, 1.5 g) in MeOH (150 mL) is hydrogenated at 40 psi for 5 h or until no more ¾ is consumed. The mixture is filtered through Celite, and the filtrate is concentrated in vacuo. The residue is dissolved in CH2CI2, and the resulting solution is dried over MgS04, filtered, and concentrated in vacuo to yield 15.0 g of the product as a yellow liquid. 1H NMR (CDC13, 300 MHz) delta 8.00 (s, 1H), 7.98 (d, J= 5.5, 1H), 6.70 (d, J= 5.4, 1H) 3.90 (s, 3H), 3.71 (br s, 2H). LC Rt: 0.57 min; LCMS m/z 125 (M+l, 100%).
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 24h;	to a solution of compound 13-1 (10.0 g, 64.9 mmol) in EtOH (400 mL) was added 10% Pd/C (w/w) (4.60 g). The reaction mixture was allowed to stir at rt under an atmosphere of ¾ for 24 hrs. Subsequently, the reaction mixture was filtered through Celite545 and the filtered cake was washed with EtOAc (100 mL x 3). The filtrate was concentrated and the residue was dried in vacuo to give crude compound 13-2 (8.0 g, 99% yield) as a dark red oil, which was used for the next step without further purification. LC-MS (ESI): m/z 125 [M+H]+.

References: [1]Patent: US2007/270433,2007,A1 .Location in patent: Page/Page column 47.
[2]Patent: WO2012/67664,2012,A1 .Location in patent: Page/Page column 53.
[3]Inorganic Chemistry,2013,vol. 52,p. 3653 - 3662.
[4]Patent: US2011/9405,2011,A1 .Location in patent: Page/Page column 49-50.
[5]European Journal of Medicinal Chemistry,2019,vol. 162,p. 32 - 50.
[6]Chemistry - A European Journal,2012,vol. 18,p. 16358 - 16368.
[7]Journal of the American Chemical Society,2015,vol. 137,p. 7552 - 7555.
[8]Bulletin de la Societe Chimique de France,1992,p. 79 - 84.
[9]Patent: US2007/167497,2007,A1 .Location in patent: Page/Page column 27.
[10],1934,vol. 2,p. 384,388.
[11]Journal of the Chemical Society, <1954> 4516, 4520,.
[12]Justus Liebigs Annalen der Chemie,1936,vol. 521,p. 286,293.
[13]Patent: WO2011/78984,2011,A1 .Location in patent: Page/Page column 62.
[14]Patent: WO2012/58125,2012,A1 .Location in patent: Page/Page column 142.
[15]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6693 - 6704.

10
[ 31872-62-5 ]
[ 146950-67-6 ]

References: [1]Chemische Berichte,1942,vol. 75,p. 1936,1942.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5.
[3]Patent: WO2008/71937,2008,A1 .

11
[ 31872-62-5 ]
[ 68-11-1 ]
[ 18504-85-3 ]

References: [1]Synthesis,1985,p. 331 - 333.

12
[ 31872-62-5 ]
[ 105-53-3 ]
[ 54415-82-6 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 406 - 414.
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 488 - 496.

13
[ 31872-62-5 ]
[ 74-88-4 ]
4-methoxy-N-methyl-3-nitropyridinium iodide [ No CAS ]

References: [1]Heterocycles,1994,vol. 37,p. 355 - 366.

14
[ 31872-62-5 ]
3-hydroxylamino-4-methoxypyridine [ No CAS ]

References: [1]Russian Chemical Bulletin,1993,vol. 42,p. 325 - 327.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 365 - 367.

15
[ 7205-98-3 ]
[ 31872-62-5 ]
2-Benzenesulfonylmethyl-4-methoxy-3-nitro-pyridine [ No CAS ]

References: [1]Polish Journal of Chemistry,1998,vol. 72,p. 1168 - 1172.

16
[ 110-71-4 ]
[ 13091-23-1 ]
[ 132038-21-2 ]
[ 31872-62-5 ]

References: [1]Heterocycles,1999,vol. 51,p. 721 - 726.

17
[ 13091-23-1 ]
[ 98-80-6 ]
[ 132038-21-2 ]
[ 31872-62-5 ]

References: [1]Heterocycles,1999,vol. 51,p. 721 - 726.

20
[ 31872-62-5 ]
[ 33544-42-2 ]

References: [1]Organic Letters,2000,vol. 2,p. 2253 - 2256.

21
[ 1826-67-1 ]
[ 31872-62-5 ]
7-methoxy-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2345 - 2347.

22
[ 31872-62-5 ]
[ 75-04-7 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	In ethanol; water; at 85℃; for 2h;	A solution consisting of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (15.0 g, 97.3 MMOL) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 MMOL) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all VOLATILES IN VACUO afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.
99%	In ethanol; water; at 85℃; for 2h;	A solution consisting of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (15.0 g, 97.3 mmol) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 mmol) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.

References: [1]Patent: WO2005/11700,2005,A1 .Location in patent: Page/Page column 84.
[2]Patent: WO2005/46678,2005,A1 .Location in patent: Page/Page column 77.
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5.
[4]Patent: WO2008/71937,2008,A1 .Location in patent: Page/Page column 21.

23
[ 31872-62-5 ]
[ 607373-82-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		Into a 1 L flask containing 250 ml_ of dry THF cooled to -78°C was condensed NH3 (100-150 ml_). Solid t-BuOK (200 mmole, 22.5 g) was added to the THF and was completely dissolved after 10 min of vigorous stirring. In a separate 500 ml_ flask, 10OmL of dry THF containing <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (12.3 g, 80 mmole) was cooled to 00C. To this solution was added t-BuOOH (88 mmole, 16 ml_). The t-BuOOH/THF solution was then added to the -78°C ammonia >solution over 20 min via dropping funnel. The reaction solution was allowed to warm to -400C and then stirred at this temperature for 1 h. The reaction was quenched with saturated NH4CI solution (20 mL) and the cooling bath removed. The reaction solution was allowed to stir overnight at RT. The precipitate was filtered and dried under vacuum to give (9.5 g, 70percent) of product as a tan solid: LC/MS: m/z 171 [M+H]+, single component.
51%	With tert.-butylhydroperoxide; potassium tert-butylate; ammonia; In tetrahydrofuran; decane; at -78 - 0℃; for 3.16667h;	Step 1. 2-Hydroxy-4-methoxy-5-nitropyridine THF (100 mL) was cooled to-78 °C and anhydrous NH3 (-200 mL) was condensed into the THF. Potassium t-butoxid (45.5 g, 405 mmol) was added and the mixture was allowed to warm to--35 °C. <strong>[31872-62-5]4-Methoxy-3-nitropyridine</strong> (25.0 g, 162 mmol) was cooled to 0 °C in THF (200 mL) and a solution of t-BuOOH (5 M in decane, 34 mL, 170 mmol) was added over 10 min. This solution was then added dropwise to the KOt-Bu solution over 1 h, then stirred for 2 h at-35 °C and then carefully quenched with-50 mL of sat. NH4C1 solution. The mixture was allowed to vent and warm to rt overnight, then the organics were concentrated and the residue made acidic with NH4C1 solution and filtered. The solid was washed with cold H20 and dried to give the title compound as a tan solid (14.0 g, 51percent).
90 g	With tert.-butylhydroperoxide; potassium tert-butylate; ammonia; In tetrahydrofuran; at -30 - -25℃; for 1h;	Example 1 Preparation of 2-hydroxy-4-methoxy-5-nitro pyridine(4-methoxy-5-nitropyridin-2-ol) Charged ammonia gas at -70° C. to a solution of THF (1800 ml). After achieving 1.0 Kg, stopped the gas flow. Charged potassium tert butoxide (182 gms). Temperature was raised to -30° C., charged a solution of <strong>[31872-62-5]4-methoxy-3-nitro pyridine</strong> (100 g) dissolved in THF (250 ml) and tert butyl hydro peroxide (144 ml) to the above mixture at -30 to -25° C. After addition, continued the reaction for 1.0 hr. Saturated ammonium chloride solution (450 ml) was cautiously added and the mixture was allowed to warm to room temperature. The ammonia was evaporated and the residue diluted with water (500 mL). The resulting solid was collected, washed with water and dried to give 2-hydroxy-4-methoxy-5-nitro pyridine(4-methoxy-5-nitropyridin-2-ol) (90.0 g).

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5.
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1508 - 1511.
[3]Patent: WO2006/113837,2006,A2 .Location in patent: Page/Page column 36; 62-63.
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 42 - 46.
[5]Patent: WO2005/37197,2005,A2 .Location in patent: Page/Page column 94.
[6]Patent: US2015/315149,2015,A1 .Location in patent: Paragraph 0043; 0053.

24
[ 31872-62-5 ]
[ 607368-91-2 ]