579514-75-3|tert-Butyl 4-fluoro-3-nitrobenzoate| Ambeed

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Quality Control of [ 579514-75-3 ] Purity: 95% SDS Specification

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Product Details of [ 579514-75-3 ]

CAS No. :	579514-75-3
Formula :	C₁₁H₁₂FNO₄
M.W :	241.22
SMILES Code :	O=C(OC(C)(C)C)C1=CC=C(F)C([N+]([O-])=O)=C1
MDL No. :	MFCD16620871
InChI Key :	QWDYAIDDFCNTKJ-UHFFFAOYSA-N
Pubchem ID :	58748597

Safety of [ 579514-75-3 ]

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

Computational Chemistry of [ 579514-75-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	60.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	72.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.14
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	2.6
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.	2.16
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	0.76
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.16

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.97
Solubility	0.258 mg/ml ; 0.00107 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.	-3.76
Solubility	0.0416 mg/ml ; 0.000172 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	-2.96
Solubility	0.263 mg/ml ; 0.00109 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	Yes
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.	-5.93 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	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)	2.21

Application In Synthesis of [ 579514-75-3 ]

* 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 [ 579514-75-3 ]

[ 579514-75-3 ] Synthesis Path-Downstream 1~35

1
[ 98946-18-0 ]
[ 453-71-4 ]
[ 579514-75-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With boron trifluoride diethyl etherate; In diethyl ether; at 20℃;Inert atmosphere;	4-Fluoro-3-nitrobenzoic acid (5.O g, 27.0 mmol) was dissolved in diethyl ether (70 mL) followed by addition of tert-butyl 2,2,2-trichloroacetimidate (6.05 ml, 32.4 mmol). BF3 OEt2 (0.137 mL, 1.08 mmol) was added dropwise via syringe, and the contents were stirred at room temperature overnight. Solid NaHCO3 (1.5 g) was added, and the mixture was stirred for an additional 30 min. The reaction mixture was diluted with ether, and the contents then concentrated in vacuo to dryness. The crude residue was purified by silica gel chromatography (eluent: 5-10% EtOAc in hexanes) to afford the product as an oil which solidifies on hi-vacuum drying (3.78 g, 58%). LC-MS (ES) m/z = 185.5 (M - t-butyl)+ 1H NMR (400 MHz, DMSO-d6) delta 8.51 (dd, J=I.3, 2.0 Hz, IH), 8.28 (ddd, J=8.6, 4.29, 2.3 Hz, IH), 7.73 (dd, J=I L l, 8.8 Hz, IH), 1.59 (s, 9 H).

References: [1]Patent: WO2005/28451,2005,A1 .Location in patent: Page/Page column 28.
[2]Patent: WO2010/126922,2010,A1 .Location in patent: Page/Page column 104.

2
[ 579514-75-3 ]
[ 765-30-0 ]
[ 579514-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol;	General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield).

References: [1]Patent: WO2005/28451,2005,A1 .Location in patent: Page/Page column 28-29.
[2]European Journal of Medicinal Chemistry,2018,vol. 147,p. 238 - 252.

3
[ 24424-99-5 ]
[ 453-71-4 ]
[ 579514-75-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With dmap; In tert-butyl alcohol; at 40℃;	To a solution of 4-fluoro-3-nitrobenzoic acid (100 g, 540.2 mmol) in t- butanol (2.5 L), DMAP (13.18 g, 108.04 mmol) and di tert-butyl dicarbonate (248 mL, 1080.4 mmol) were added and the reaction mixture was heated at 40C overnight. Upon completion, the reaction mixture was diluted with FLO and the aqueous phase was extracted with EtOAc (3 x 1.5 L). The combined organic layer was washed further with H20 (lx 1L), brine (lx 1L), and dried over Na2S04. The solvent was removed under reduced pressure and the crude material thus obtained was purified by column chromatography (100-200 mesh size S1O2 gel, eluting with a gradient of 100% Hex to 5% EtOAc in Hex) affording pure ter?-butyl-4-fluoro-3-nitrobenzoate (70 g, 54%) as light yellow solid.
54%	With dmap; In tert-butyl alcohol; at 40℃;	To a solution of 4-fluoro-3-nitrobenzoic acid (100 g, 540.2 mmol) in tbutanol (2.5 L), DMAP (13.18 g, 108.04 mmol) and di tert-butyl dicarbonate (248 mL, 1080.4 mmol) were added and the reaction mixture was heated at 40C overnight. Upon completion, the reaction mixture was diluted with H20 and the aqueous phase was extracted with EtOAc (3 x 1.5 L). The combined organic layer was washed further with H20 (lx 1L), brine (lx 1L), and dried over Na2SO4. Thesolvent was removed under reduced pressure and the crude material thus obtained was purified by column chromatography (100-200 mesh size Si02 gel, eluting with a gradient of 100% hexane to 5% EtOAc in hexane) affording pure tertbutyl-4-fluoro-3-nitrobenzoate (70 g, 54%) as light yellow solid.
54%	With dmap; In tert-butyl alcohol; at 40℃;	To a solution of 4-fluoro-3-nitrobenzoic acid (100 g, 540.2 mmol) in /-butanol (2.5 L), DMAP (13.18 g, 108.04 mmol) and di tert-butyl dicarbonate (248 mL, 1080.4 mmol) were added and the reaction mixture was heated at 40C overnight. Upon completion, the reaction mixture was diluted with H2O and the aqueous phase was extracted with EtOAc (3 x 1.5 L). The combined organic layer was washed further with H2O (lx 1L), brine (lx 1L), and dried over Na2SC>4. The solvent was removed under reduced pressure and the crude material thus obtained was purified by column chromatography (100-200 mesh size S1O2 gel, eluting with a gradient of 100% Hex to 5% EtOAc in Hex) affording pure tert- butyl - 4-fluoro-3-nitrobenzoate (70 g, 54%) as light yellow solid.

49.8%	With dmap; In tert-butyl alcohol; for 24h;	To a solution of 4-fluoro-3-nitro benzoic aicd (370 mg, 2 mmol) in 10 mL of t-BuOH were added (BoC)2O (872 mg, 4 mmol) and DMAP (24 mg, 0.2 mmol). The solution was stirred for 24 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with IN HCl. The separated organic phase was evaporated. The residue was subjected to a flash column chromatography on silica gel eluting with 12.5% EtOAc/Petroleum ether to give compound 0201 (240mg, 49.8%). 1H NMR (DMSO-J6): delta 1.55 (s, 9H), 7.69 (m, IH), 8.26 (m, IH), 8.48 (m, IH).
43%	With dmap; In tetrahydrofuran; at 20℃; for 24h;	To a solution of 4-fluoro-3-nitro benzoic aicd (33) (5 g, 27 mmol) in 30 mL ofTHF were added (Boc)2O (6.25 mL, 54 mmol) and DMAP (329 mg, 2.7 mmol). Thesolution was stirred at room temperature for 24 h. The solvent was evaporated. Theresidue was dissolved in ethyl acetate and washed with 1 N HCl. The separatedorganic phase was evaporated. The residue was subjected to a flash columnchromatography on silica gel eluting to give tert-butyl 4-fluoro-3-nitrobenzoate (34)(2.24 g, 43% yield).

References: [1]Patent: WO2016/33486,2016,A1 .Location in patent: Page/Page column 65.
[2]Patent: WO2018/183418,2018,A1 .Location in patent: Page/Page column 783; 784.
[3]Patent: WO2019/173181,2019,A1 .Location in patent: Page/Page column 68.
[4]Patent: WO2009/36051,2009,A1 .Location in patent: Page/Page column 57.
[5]European Journal of Medicinal Chemistry,2018,vol. 147,p. 238 - 252.

4
[ 110-85-0 ]
[ 579514-75-3 ]
[ 1012060-12-6 ]

Yield	Reaction Conditions	Operation in experiment
70.7%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 6h;	A mixture of piperazine(451 mg, 5.2 mmol), tert-butyl 4-fluoro-3-nitro-benzoate (211 mg, 0.9 mmol) and K2CO3 (234 mg, 1.7 mmol) in DMF(IO ml) was stirred at 12O0C for 6 hours. The mixture was poured into water, and extracted with ethyl acetate. The organic phase was washed with water (100 ml), concentrateded in vacuo. The residue was purified with flash column chromatography on silica gel eluting with 25% ethyl acetate/petroleum ether to provide 0202 (190 mg, 70.7%). LC-MS: 308 [M+l]+. 1H NMR (CDCl3): delta 1.58 (s, 9H), 1.84 (s, IH), 3.01 (m, 4H), 3.12 (m, 4H), 7.03 (d, J= 6.0 Hz, IH), 8.02 (dd, J= 2.1, 6.0 Hz, IH), 8.33 (d, J= 2.1 Hz, IH).

References: [1]Patent: WO2009/36051,2009,A1 .Location in patent: Page/Page column 57.

5
[ 453-71-4 ]
[ 36805-97-7 ]
[ 579514-75-3 ]

Yield	Reaction Conditions	Operation in experiment
16%	In toluene; at 100℃; for 20h;	To a 2L high pressure vessel were added 4-fluoro-3-nitrobenzoic acid (25 g, 135 mmol), dimethylformamide di-t-butylacetal (162 ml, 675 mmol), and toluene (200 ml). The vessel was sealed and heated to 1000C for 20 hours. The mixture was cooled to ambient temperature. The mixture was transferred to 100 mL of EtOAc and 100 ml of IN HCl and the layers were separated. The organic layer was washed with IN HCl, water, and brine, dried over MgSO4, filtered through a medium frit filter, and concentrated. The crude was purified on silica gel (EtOAc in hexanes gradient) to provide 5. Ig of the title compound were obtained as light yellow solid (16%).

References: [1]Patent: WO2009/158426,2009,A1 .Location in patent: Page/Page column 110.

6
[ 579514-75-3 ]
[ 1202889-99-3 ]
[ 1202890-00-3 ]

Yield	Reaction Conditions	Operation in experiment
65%		To a stirred solution of ethyl 8-bromo-6- chloro-7-hydroxychroman-4-carboxylate (4.00 g, 11.9 mmol) and tert-butyi 4-fluoro-3- nitrobenzoate (3.16 g, 13.1 mmol) in Lambda/,Lambda/-dimethylformamide (66 mL) at ambient temperature was added solid potassium carbonate (2.64 g, 19.1 mmol). The resulting mixture was stirred in an oil bath set to 900C for 30 minutes. The mixture was cooled to ambient temperature and poured into a separatory funnel containing water (600 mL). Chloroform (300 mL) was added, followed by IM hydrochloric acid (100 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 90/10 hexanes/ethyl acetate to afford the desired compound as a light yellow glass (4.33 g, 65% yield).
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 0.5h;	To a stirred solution of ethyl 8-bromo-6- <n="101"/>chloro-7-hydroxychroman-4-carboxylate (4.00 g, 11.9 mmol) and tert-butyl 4-fluoro-3- nitrobenzoate (3.16 g, 13.1 mmol) in Lambda/,Lambda/-dimethylformamide (66 mL) at ambient temperature was added solid potassium carbonate (2.64 g, 19.1 mmol). The resulting mixture was stirred in an oil bath set to 900C for 30 minutes. The mixture was cooled to ambient temperature and poured into a separatory funnel containing water (600 mL). Chloroform (300 mL) was added, followed by IM hydrochloric acid (100 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 90/10 hexanes/ethyl acetate to afford ethyl 8-bromo-7-(4-(tert- butoxycarbonyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate as a light yellow glass (4.33 g, 65% yield).

References: [1]Patent: WO2010/75200,2010,A1 .Location in patent: Page/Page column 122.
[2]Patent: WO2009/158426,2009,A1 .Location in patent: Page/Page column 99-100.

7
[ 579514-75-3 ]
[ 1202890-12-7 ]
[ 1233696-44-0 ]

Yield	Reaction Conditions	Operation in experiment
62.3%		A mixture of ethyl 6,8-dichloro-7-hydroxychroman-4- carboxylate (2.50 g, 8.59 mmol), <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (2.20 g, 9.12 mmol) and potassium carbonate (1.8 g, 13 mmol) in 50 mL of NMP was degassed with argon for 10 minutes and was heated at 80 0C overnight. After stirring overnight the reaction mixture was cooled to ambient temperature and diluted with 600 mL of water. The pH was adjusted to 1-2 with 1 N HCl and the resulting solids were collected by filtration. The solids were dissolved in ethyl acetate and the solution was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 20% ethyl acetate in hexanes to give ethyl 7-(4-(tert-butoxycarbonyl)-2- nitrophenoxy)-6,8-dichlorochroman-4-carboxylate (2.74 g, 62.3% yield) as an oil.
		A mixture of ethyl 6,8-dichloro-7-hydroxychroman-4- carboxylate (35 g, 120.22 mmol), <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (31.1 g, 128.93 mmol), K2CO3 (24.923 g, 180.33 mmol), and l-methyl-2-pyrrolidinone (500 mL) was purged with Argon (bubbled through) for 15 minutes. The mixture was heated to 80 0C for 4 hours under Argon atmosphere. The mixture was cooled to ambient temperature and poured into 3 liters of water. The pH was adjusted to pH 2 by addition of concentrated HCl (4 X 10 ml). A solid precipitated out as HCl was added and gas evolution was observed. The crude mixture was filtered and the solid was dissolved in EtOAc (1 liter). The EtOAc solution was washed with 2N HCl solution (200 ml), water (2 X 200 ml), and brine (200 ml), dried over MgSO4, filtered, and concentrated to provide 64.1g of the title compound as a dark solid (104%).

References: [1]Patent: WO2010/75200,2010,A1 .Location in patent: Page/Page column 55.
[2]Patent: WO2009/158426,2009,A1 .Location in patent: Page/Page column 111.

8
[ 107-10-8 ]
[ 579514-75-3 ]
[ 1253738-85-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	In tetrahydrofuran; at 20℃;Inert atmosphere; Cooling with ice;	1 , 1 -Dimethylethyl 4-fluoro-3-nitrobenzoate (3.78 g, 15.67 mmol) was dissolved in 100 mL THF and the stirring solution cooled in an ice bath for 15 min, followed by addition of n- propylamine (2.74 ml, 32.9 mmol) via syringe. The stirring solution was allowed to warm to room temperature, and then stirred overnight. The reaction mixture was concentrated to dryness, and the residue dissolved in EtOAc (100 mL) and brine (100 mL). The layers were separated, and the aqueous layer extracted with additional EtOAc (100 mL). The combined organic layers were dried over MgSO/t, filtered, and concentrated in vacuo. The collected product was dried on hi-vac pump at room temperature for 4 h to afford the product as a yellow-orange solid (4.28 g, 97%). LC-MS (ES) m/z = 281.0 (M + H)+ 1H NMR (400 MHz, DMSO-d6) delta 8.44 - 8.64 (m, 2 H), 7.92 (dd, J=8.8, 2.0 Hz, IH), 7.13 (d, J=9.4 Hz, IH), 3.35 - 3.45 (m, 2H), 1.59 - 1.71 (m, 2H), 1.48 - 1.59 (m, 9H), 0.94 (t, J=7.3 Hz, 3H).
	With N-ethyl-N,N-diisopropylamine; In ethanol;	General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield).

References: [1]Patent: WO2010/126922,2010,A1 .Location in patent: Page/Page column 104-105.
[2]European Journal of Medicinal Chemistry,2018,vol. 147,p. 238 - 252.

9
[ 453-71-4 ]
[ 115-11-7 ]
[ 579514-75-3 ]