369-26-6|Methyl 3-amino-4-fluorobenzoate| Ambeed

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Quality Control of [ 369-26-6 ] Purity: 97% SDS Specification

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Product Details of [ 369-26-6 ]

CAS No. :	369-26-6
Formula :	C₈H₈FNO₂
M.W :	169.15
SMILES Code :	NC1=C(C=CC(=C1)C(=O)OC)F
MDL No. :	MFCD08689743
InChI Key :	ABELEDYNIKPYTP-UHFFFAOYSA-N
Pubchem ID :	12541234

Safety of [ 369-26-6 ]

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

Computational Chemistry of [ 369-26-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	42.08
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.7
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	1.74
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.62
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.	1.75
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	1.4
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.22
Solubility	1.01 mg/ml ; 0.00598 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.	-2.46
Solubility	0.593 mg/ml ; 0.0035 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	-2.39
Solubility	0.692 mg/ml ; 0.00409 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.	-6.1 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	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)	1.38

Application In Synthesis of [ 369-26-6 ]

* 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 [ 369-26-6 ]

[ 369-26-6 ] Synthesis Path-Downstream 1~35

1
[ 369-26-6 ]
[ 125568-76-5 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 10033 - 10046.

2
[ 125568-76-5 ]
[ 369-26-6 ]
[ 125568-88-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.

3
[ 369-26-6 ]
[ 100-52-7 ]
[ 125568-82-3 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.

4
[ 125568-76-5 ]
[ 109-89-7 ]
[ 369-26-6 ]
[ 125569-04-2 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.
[2]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.

5
[ 456-22-4 ]
[ 369-26-6 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.
[2]Tetrahedron,2019,vol. 75,p. 4010 - 4016.

6
[ 369-26-6 ]
[ 125568-88-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2034 - 2044.

7
[ 369-26-6 ]
[ 18063-02-0 ]
[ 1160624-36-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With triethylamine; at 20℃; for 1.5h;	Step C: Methyl 3-[(2,6-difluorophenyl)carbonyl]amino}-4-fluorobenzoate; To a solution of <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (5.5 g, 33 mmol) in DCM (100 ml_) was added TEA (6.8 ml_, 49 mmol) and 2,6-difluorobenzoyl chloride (4.3 ml_, 34 mmol). After 90 min at rt, the reaction mixture was washed with H2O and concentrated to a brown oil. The product was purified by column chromatography (eluting with 30-60percent EtOAc /hexanes) to generate the desired product in 52percent yield (5.37 g, 17 mmol). MS (ESI) m/z = 310 [M+Hf .

References: [1]Patent: WO2009/76140,2009,A1 .Location in patent: Page/Page column 187.

8
[ 26120-86-5 ]
[ 369-26-6 ]
[ 1195768-44-5 ]

Yield	Reaction Conditions	Operation in experiment
94.5%	With pyridine;dmap; In dichloromethane; at 0 - 20℃;	Intermediate 35: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide; Step A: Methyl 3-(2,5-difluorophenylsulfonamido)-4-fluorobenzoate; To a solution of <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (25 g, 149 mmol) in DCM (150 mL) were added pyridine (35.3 g, 446 mmol) and a catalytic amount of DMAP (1.8 g, 14.9 mmol). The mixture was cooled to 0 C. 2,5-Difluorobenzene-1-sulfonyl chloride (34.7 g, 212 mmol) in DCM (20 mL) was added dropwise to the mixture. The reaction was stirred at rt overnight. Then the reaction was washed with water (300 mL), and extracted with DCM (2×400 mL). The organic layer was washed with brine, dried over anhydrous NaSO4, filtrated and concentrated under reduced pressure to give the crude product, which was washed with petroleum ether to afford the title compound of Step A (48.2 g, 94.5% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.12-8.18 (m, 1H), 7.73-7.80 (m, 1H), 7.47-7.53 (m, 1H), 7.10-7.25 (m, 1H), 7.00-7.07 (m, 1H), 3.86 (s, 3H).

References: [1]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 60.

9
[ 369-26-6 ]
[ 2937-50-0 ]
[ 1195768-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20℃;	Intermediate 37: 2-Propen-1-yl {5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate; Step A: Methyl 4-fluoro-3-[(2-propen-1-yloxy)carbonyl]amino}benzoate; To a solution of <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (109 g, 644 mmol) in THF (2000 mL), saturated NaHCO3 (68 g, 805 mmol) was added. Then 2-propen-1-yl chloridocarbonate (93 g, 773 mmol) was added dropwise at 0 C. The mixture was stirred at rt for 2 h. The solution was extracted with EtOAc (500 mL×3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product (160 g, 98%), which was used in the next step directly. 1H NMR (400 MHz, CDCl3) delta ppm 8.72-8.81 (m, 1H), 7.71-7.79 (m, 1H), 7.09-7.16 (m, 1H), 6.87-6.94 (br, 1H), 5.91-6.03 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5, 1H), 4.70 (d, J=10.5 Hz, 1H), 4.70 (d, J=5.5 Hz, 2H), 3.90 (s, 3H).

References: [1]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 61.

10
[ 776-04-5 ]
[ 369-26-6 ]
C₁₅H₁₁F₄NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃;Inert atmosphere;	Methyl 3-amino-4-fluorobenzoate (2 g, 13 mmol) and pyridine (2.1 g, 76.4 mmol) were suspended in DCM (25 mL), and to the stirring solution was slowly added 2-trifluoromethyl- benzenesulfonyl chloride (3.24 g, 13 mmol) at room temperature. After stirring for 2 h, the reaction mixture was washed with water and then extracted with DCM. The combined organic layers were dried over Na2SOzI, filtered, and concentrated in vacuo. The crude residue was suspended in water (30 mL) followed by slow addition of NaOH (1.1 g, 28 mmol), and the mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was extracted with DCM. The layers were separated. The aq. layer adjusted to pH 5 with aq. 5N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the final product as a solid (4.0 g, 83percent overall). LC-MS (ES) m/z = 364.1 (M+H)+ 1H NMR (400 MHz, DMSO-d6) delta ppm 10.61 (br, 1 H), 10.37 (br, 1 H), 8.78 (m, 1 H), 8.37 (m, 1 H), 8.01 (m, 2 H), 7.71 (m, 2 H), 7.31 (m, 2 H).

References: [1]Patent: WO2010/126922,2010,A1 .Location in patent: Page/Page column 62-63.

11
[ 50-00-0 ]
[ 369-26-6 ]
[ 1258418-30-2 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 3-(dimethylamino)-4-fluorobenzoate:; In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (1.55 g, 9.16 mmol), paraformaldehyde (8.25 g, 91.63 mmol) and NaBH3CN (1.73 g, 27.49 mmol) was treated with acetic acid (90 ml.) and the resulting mixture was stirred at rt for 4 h. Sat. aq. Na2CO3 was added to the reaction mixture and the pH was adjusted to 7-8. The mixture was extracted with CH2CI2 (3 x 55 ml.) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 05c with a Waters Atlantis T3, 5mum, 4.6X30 mm column: tR = 0.76 min; [M+H]+ = 198.38.

References: [1]Patent: WO2010/143116,2010,A1 .Location in patent: Page/Page column 61.

12
[ 675-10-5 ]
[ 369-26-6 ]
[ 586379-97-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4066 - 4071.

13
[ 369-26-6 ]
[ 586380-12-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4066 - 4071.

14
[ 369-26-6 ]
[ 586380-98-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4066 - 4071.

15
[ 369-26-6 ]
C₁₄H₁₁BrFNO₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4066 - 4071.

16
[ 369-26-6 ]
[ 586380-11-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4066 - 4071.

17
[ 67-56-1 ]
[ 2365-85-7 ]
[ 369-26-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; at 0℃; for 12h;Reflux;	To a stirred solution of 3-amino-4-fluoro-benzoic acid (25 g, 161 mmol) in methanol (300 mL) was added thionyl chloride (30 mL, 403 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-fluoro-benzoic acid methyl ester (27.5 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8FNO2 (M+H)+: 170.16, observed: 169.9
89%	With sulfuric acid; for 20h;Reflux;	Step 1: Preparation of methyl 3-amino-4-fluorobenzoate (54) To a mixture of 3-amino-4-fluorobenzoic acid (1 g, 6.45 mmol) in MeOH (20 ml), conc. H2SO4 (0.687 ml, 12.89 mmol) was added drop wise, and the reaction was refluxed for 20 hours. After cooling to room temperature the solvent was evaporated and the residue was partitioned between aq. NaHCO3 sat. sol. and ethyl acetate; the organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness affording methyl 3-amino-4-fluorobenzoate as a brown solid (0.970 g, 5.73 mmol, 89percent yield, MS/ESI+170.0 [MH]+) (43)
290 mg	With sulfuric acid;Reflux;	3-amino-4-fluorobenzoic acid (0.5g) was dissolved in methanol (lOml), then concentrated sulfuric acid (lml) was added. The reaction solution was heated to reflux until the reaction is complete. Then the reaction mixture was cooled down and poured into water, the pH of the resultant solution was adjusted to 8 by 2N NaOH solution. The product was extracted to EtOAc layer and the solvent was stripped off. 290mg of methyl 3-amino-4- fluorobenzoate was obtained.

References: [1]Patent: US2011/257151,2011,A1 .Location in patent: Page/Page column 92.
[2]Patent: US2014/155391,2014,A1 .Location in patent: Paragraph 0392; 0393.
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[4]Patent: WO2014/106019,2014,A2 .Location in patent: Paragraph 0689; 0690.
[5]Journal of Medicinal Chemistry,2016,vol. 59,p. 2423 - 2435.

18
[ 60230-36-6 ]
[ 369-26-6 ]
[ 1351161-81-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362.

19
[ 369-26-6 ]
[ 1244642-01-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362.

20
[ 369-26-6 ]
[ 1195768-42-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362.

21
[ 369-26-6 ]
[ 1195768-43-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362.

22
[ 369-26-6 ]
C₁₈H₁₀BrClF₃N₃O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4436 - 4440.
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362.

23
[ 369-26-6 ]
[ 1343461-33-5 ]