[ CAS No. 73792-12-8 ] {[proInfo.proName]}

Name: 73792-12-8|Ethyl 4-amino-3-fluorobenzoate|97%
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SKU: A106172
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Quality Control of [ 73792-12-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73792-12-8 ]

SDS Specification

Alternatived Products of [ 73792-12-8 ]

Product Details of [ 73792-12-8 ]

CAS No. :	73792-12-8	MDL No. :	MFCD07782043
Formula :	C₉H₁₀FNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SPGMDXDPJKEDGC-UHFFFAOYSA-N
M.W :	183.18	Pubchem ID :	20536493
Synonyms :

Calculated chemistry of [ 73792-12-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.89
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.01
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.9

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.44
Solubility :	0.662 mg/ml ; 0.00361 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.272 mg/ml ; 0.00148 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.291 mg/ml ; 0.00159 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 73792-12-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 73792-12-8 ]

* 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 [ 73792-12-8 ]
Downstream synthetic route of [ 73792-12-8 ]

[ 73792-12-8 ] Synthesis Path-Upstream 1~2

1
[ 144267-96-9 ]
[ 73792-12-8 ]

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6191 - 6194

2
[ 73792-12-8 ]
[ 78485-37-7 ]

Reference： [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032

[ 73792-12-8 ] Synthesis Path-Downstream 1~57

1
[ 73792-12-8 ]
[ 112-82-3 ]
[ 73792-13-9 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1393 - 1411

2
[ 73792-12-8 ]
[ 73792-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1393 - 1411

3
[ 620-86-0 ]
[ 73792-12-8 ]
[ 1133948-19-2 ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 4-(4-benzylbenzamido)-3-fluorobenzoate A solution of 4-benzylbenzoic acid (1.06 g, 5 mmole) in dichloromethane (10 mL) was added oxalyl dichloride (1 mL) followed by a few drops of DMF at 0 C. The resulting mixture was stirred room temperature for 3 hours. Removal of the solvents gave the residue which was dissolved in dichloromethane (2 mL) and added to the solution of triethylamine (1.4 mL, 10 mmol) and <strong>[73792-12-8]ethyl 4-amino-3-fluorobenzoate</strong> (916 mg, 5 mmole) in dichloromethane (50 mL) at 0 C. After stirring at room temperature for 48 hours, the mixture was washed with saturated sodium bicarbonate and 1 N HCl. The combined organic extracts were washed with brine, dried and concentrated under reduced pressure to give the residue which was purification by silica gel chromatography on ISCO system. The desired product was obtained as an off white solid: 1H NMR (400 MHz, CDCl3) delta 8.63 (t, J=8.8 Hz, 1H), 8.20 (s, 1H), 7.83 (m, 4H), 7.18-7.35 (m, 6H), 4.39 (q, J=7.2 Hz, 1H), 4.07 (s, 2H), 1.40 (t, J=7.2 Hz, 3H).

Reference： [1]Patent: US2009/82331,2009,A1 .Location in patent: Page/Page column 16

4
[ 1219496-27-1 ]
[ 73792-12-8 ]
[ 1219496-28-2 ]

Yield	Reaction Conditions	Operation in experiment
10%		5.2 4-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acid ethyl ester To a solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (60 mg, 161 mumol) in CH2Cl2 (0.8 ml) under an argon atmosphere was added pyridine (16 mul, 202 mumol) and thionyl chloride (14 mul, 193 mumol). 4-Amino-3-fluoro-benzoic acid ethyl ester (29 mg, 161 mumol; CAS Reg. No. 73792-12-8) and pyridine (16 mul, 202 mumol) were added and the reaction mixture was stirred at ambient temperature for 48 h. Ice water/25% aqueous HCl solution 1/1 was added and the mixture was extracted three times with CH2Cl2. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give a brown solid which was purified by preparative thick layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (9 mg, 16 mumol; 10%) as colorless solid. MS: m/e=554.4 [M+H+].

Reference： [1]Patent: US2010/76027,2010,A1 .Location in patent: Page/Page column 27-28

6
[ 1369872-05-8 ]
[ 73792-12-8 ]
[ 1369872-16-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With caesium carbonate;1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In 1,4-dioxane; at 85℃; for 1h;	Example 1.13: Preparation of 3-Fluoro-4-(5-fluoro-6-(4-(3-(2-fluoropropan-2-yl)-l,2,4- oxadiazol-5-yl)piperidin-l-yl)pyrimidin-4-ylamino)-/Vimethylbenzamide (Compound 2).Step A: Preparation of Ethyl 3-Fluoro-4-(5-fluoro-6-(4-(3-(2-fluoropropan-2-yl)- l,2,4-oxadiazol-5-yl)piperidin-l-yl)pyrimidin-4-ylamino)benzoate.A suspension of 5-(l-(6-chloro-5-fluoropyrimidin-4-yl)piperidin-4-yl)-3-(2- fluoropropan-2-yl)-l ,2,4-oxadiazole (1.0 g, 2.91 mmol), <strong>[73792-12-8]ethyl 4-amino-3-fluorobenzoate</strong> (0.533 g, 2.91 mmol), diacetoxypalladium (0.098 g, 0.436 mmol), 1 ,1 '-bis (di-i- butylphosphino)ferrocene (0.414 g, 0.873 mmol), and Cs2C03 (2.464 g, 7.56 mmol) in dioxane (10 mL) was heated conventionally at 85C for 1 h. Reaction was quenched with water and extracted with AcOEt. The organic layer was concentrated to give a residue and the residue was purified by prep-HPLC. Fractions containing desired product were combined, basified with saturated NaHC03 (aq), partially concentrated under vacuum, and extracted with AcOEt. The organic layer was rinsed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (1.0 g, 2.039 mmol, 70 % yield). Exact mass calculated for C23H25F3N6O3: 490.2, found: LCMS m/z = 491.3 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.39 (t, = 7.07 Hz, 3H), 1.77 (s, 3H), 1.82 (s, 3H), 1.97-2.08 (m, 2H), 2.17-2.25 (m, 2H), 3.22-3.33 (m, 3H), 4.37 (q, = 7.07 Hz, 2H), 4.42-4.50 (m, 2H), 7.04-7.10 (m, 1H), 7.78 (dd, = 11.87, 1.89 Hz, 1H), 7.84-7.89 (m, 1H), 8.15-8.18 (m, 1H), 8.66 (t, = 8.46 Hz, 1H).

Reference： [1]Patent: WO2012/40279,2012,A1 .Location in patent: Page/Page column 94 percent

7
[ 97603-39-9 ]
[ 73792-12-8 ]
ethyl 3-fluoro-4-[2-(pyridin-3-yl)pyrimidin-4-yl]amino}benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With hydrogenchloride; In ethanol; water;Reflux;	General procedure: General procedure G A mixture of starting pyrimidine derivative (1.0 eq.), aryl amine (1.0 eq.) and HCI (cone, 3 drops) in aqueous ethanol (4 mL ethanol with 2 mL of water) was stirred reflux overnight. The mixture was allowed to cool to room temperature then was diluted with water and aqueous ammonia and a saturated solution of NaHC03 was added stepwise. The product was extracted with dichloromethane and combined organic extracts were washed with water, brine and dried over MgS04, and concentrated in vacuo. A column chromatography of a residue afforded product as a base which was further converted to hydrochloride salt by treatment with HCI. Example 41: ethyl 3-fluoro-4-((2-(pyridiii-3-yl)pyriniidin-4-yl)amino)beiizoate hydrochloride (AMR-823) AMR-823 The title compound was prepared from 4-chloro-2-( yridin-3-yl)-pyrimidine (0.36 g, 1.88 mmol), <strong>[73792-12-8]ethyl 4-amino-3-fluorobenzoate</strong> (0.38 g, 2.07 mmol) and HCl (cone, 3 drops) according to the general procedure G. A column chromatography (eluent DCM:methanol /10:1) yielded 0.20 g (31 %) of base which was converted to hydrochloride salt by treatment with HCl. Base; 1H NMR (400 MHz, DMSO) delta 9.85 (s, 1H), 9.43 (d, J= 1.4 Hz, 1H), 8.69 (dd, J= 4.7, 1.6 Hz, 1H), 8.62 - 8.47 (m, 3H), 7.89 (d, J= 8.6 Hz, 1H), 7.78 (dd, J= 11.8, 1.7 Hz, 1H), 7.54 (dd, J= 7.4, 4.8 Hz, 1H), 7.07 (d, J= 5.8 Hz, 1H), 4.31 (q, 7= 7.1 Hz, 2H), 1.33 (t, 7= 7.1 Hz, 3H) Salt; mp 158-161 C (methanol); 1H NMR (400 MHz, DMSO) 5 10.39 (s, 1H), 9.45 (d, 7 = 1.9 Hz, 1H), 9.20-9.06 (m, 1H), 9.01 (dd, J= 5.5, 1.2 Hz, 1H), 8.57 (d, 7 = 6.0 Hz, 1H), 8.39 (t, 7 = 8.3 Hz, 1H), 8.10 (dd, J= 8.1 , 5.5 Hz, 1H), 7.87 (dd, J= 8.5, 1.9 Hz, 1H), 7.77 (dd, 7= 11.5, 1.9 Hz, 1H), 7.23 (d, J= 6.0 Hz, 1H), 4.31 (q, J= 7.1 Hz, 2H), 1.33 (t, 7= 7.1 Hz, 3H). 13C NMR (100 MHz, DMSO) 5 164.4, 160.4, 158.1, 155.2 (2C), 152.95 (JC-F = 246.6 Hz), 144.6, 142.3 (7C- F = 20.4 Hz), 134.9, 131.1 (JC-F = 11.1 Hz), 126.9, 125.8 (7C-F = 2.3 Hz), 125.5 (JC-F = 6.6 Hz), 123.1, 116.1 (Jc-F = 21.2 Hz), 108.1, 108.1, 60.9, 14.1. HR-MS (ESI) calcd. for Ci8H16F02N4 [M+H+] 339.1252, found 339.1251.
31%	With hydrogenchloride; In ethanol; water;Reflux;	General procedure: A mixture of starting pyrimidine derivative (1.0 eq.), aryl amine (1.0 eq.) and HCl (conc., 3drops) in aqueous ethanol (4 mL ethanol with 2 mL of water) was stirred with refluxovernight. The mixture was allowed to cool to room temperature, then it was diluted withwater and aqueous ammonia and a saturated solution of NaHCO3 was then added stepwise.The product was extracted with DCM and combined organic extracts were washed withwater, brine and dried over MgSO4, and concentrated in vacuo. A column chromatography ofa residue afforded product as a base which was further converted to hydrochloride salt bytreatment with HCl.

Reference： [1]Patent: WO2014/128213,2014,A1 .Location in patent: Page/Page column 55-56
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3487 - 3490

8
[ 73792-12-8 ]
C₂₂H₁₄Cl₂FN₃O₅ [ No CAS ]