58656-98-7|tert-Butyl 4-fluorobenzoate| Ambeed

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Quality Control of [ 58656-98-7 ] Purity: 98% SDS Specification

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Product Details of [ 58656-98-7 ]

CAS No. :	58656-98-7
Formula :	C₁₁H₁₃FO₂
M.W :	196.22
SMILES Code :	O=C(OC(C)(C)C)C1=CC=C(F)C=C1
MDL No. :	MFCD01320759
Boiling Point :	No data available
InChI Key :	ZZLARVGXLOCKHG-UHFFFAOYSA-N
Pubchem ID :	2736444

Safety of [ 58656-98-7 ]

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

Computational Chemistry of [ 58656-98-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	52.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.73
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	2.86
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.2
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.	3.25
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	2.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.98

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.98
Solubility	0.207 mg/ml ; 0.00105 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.	-3.07
Solubility	0.167 mg/ml ; 0.000849 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	-3.58
Solubility	0.0516 mg/ml ; 0.000263 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	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.	-5.47 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)	1.56

Application In Synthesis of [ 58656-98-7 ]

* 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 [ 58656-98-7 ]

[ 58656-98-7 ] Synthesis Path-Downstream 1~35

1
[ 40499-83-0 ]
[ 58656-98-7 ]
[ 94930-28-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In dimethyl sulfoxide; at 136℃; for 7h;	Example 31a; 7V-(2-Amino-5-(5-chlorothiophen-2-yl)phenyl)-4-(3-morpholinopyrrolidin-l-yl)benzamide(271); Ste 1 : tert-Butyi 4-(3-hvdroxypyrrolidin-l-yl)benzoate (266); [0900] A mixture of fluoride 97 (2.24 g, 11.4 mmol), pyrrolidin-3-ol (1.37 g, 15.8 mmol) and potassium carbonate (2.24 g) was suspended in dimethyl sulfoxide (5 mL) and stirred at 136 0C for 7 h. The reaction mixture was cooled to room temperature, diluted with DCM, washed with H2O, dried over MgSO4, filtered and concentrated to provide title compound 266 (3.93 g, 100%). <n="152"/>[0901] LRMS: 263.3 (calc) 264.1 (obs)

References: [1]Patent: WO2007/118137,2007,A1 .Location in patent: Page/Page column 150-151.
[2]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1241 - 1250.
[3]Journal of Organic Chemistry,1985,vol. 50,p. 1010 - 1014.

2
[ 5382-16-1 ]
[ 58656-98-7 ]
[ 95017-91-7 ]

References: [1]Journal of Organic Chemistry,1985,vol. 50,p. 1005 - 1010.

3
[ 1003-29-8 ]
[ 58656-98-7 ]
4-(2-Formyl-pyrrol-1-yl)-benzoic acid tert-butyl ester [ No CAS ]

References: [1]Synthetic Communications,1994,vol. 24,p. 123 - 129.

4
[ 487-89-8 ]
[ 58656-98-7 ]
4-(3-Formyl-indol-1-yl)-benzoic acid tert-butyl ester [ No CAS ]

References: [1]Synthetic Communications,1994,vol. 24,p. 123 - 129.

5
[ 36193-65-4 ]
[ 58656-98-7 ]
1-[4-(tert-butoxycarbonyl)phenyl]-2-cyanoindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide;	A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of <strong>[36193-65-4]2-cyanoindole</strong>, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-<strong>[36193-65-4]2-cyanoindole</strong> as an oil.

References: [1]Synthetic Communications,1994,vol. 24,p. 123 - 129.
[2]Patent: US5380739,1995,A .

6
[ 58656-98-7 ]
[ 130985-87-4 ]
(+/-)-cis-3-amino-9-<4-(tert-butoxycarbonyl)phenyl>-1-oxo-5,6,6a,7,8,9,10,10a-octahydro-2H-pyrimido<4,5-c><2,6>naphthyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 611 - 616.

7
[ 403-43-0 ]
[ 75-65-0 ]
[ 58656-98-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium t-butanolate; In neat (no solvent); at 100℃; for 1h;Inert atmosphere; Microwave irradiation;	General procedure: The reaction methods used for all the reactions shown in Tables2-4 are the same except for cholesterol, 1e where 1.0 mL of 1,4-dioxane was added. An oven dry clean microwave vial is loadedwith 1.0 mmol of NaOtBu (100.0 mg), 0.0025 mmol of PdCl2(dtbpf)(2.0 mg), capped with air-tight silicon septa and flushed withargon. Then 0.5 mmol of aroyl chloride was added as limiting reagentvia micro syringe, and tertiary alcohol (1.0 mL) was added via drysyringe. The resulting reaction mixture was then microwaved(CEM Explorer 24, 300 W) at 100 C for 60 min. Crude reaction productin reaction tube was diluted with dichloromethane and transferredinto a separating funnel. Water was then added to the funneland, after standard extraction, excess alcohol was completely misciblewith water. The bottom organic layer was collected in a smallErlenmeyer flask over anhydrous Na2SO4. The dichloromethanelayer was filtered through sintered funnel and filtrate, collectedin a round bottom flask, and completely dried by rotary evaporator and under reduced pressure in vacuo. In case of cholesterol 1e,0.5 mmol of aroyl chloride, 1.0 mmol of cholesterol, and 1.0 mLof 1,4-dioxane were used. The desired ester product was confirmedby 1H NMR, 13C NMR, and 19F NMR.
816 g	With triethylamine; In toluene; at 45 - 60℃;	The 445.0g t-butanol was added dropwise a toluene solution of the intermediate step 1, tert-butyl alcohol after the completion of the dropwise addition, the body again based 759.0g of triethylamine was added dropwise, 45-60 deg.] C after the reaction, the reaction embodies After adding 3000 g of water, stirring for 10 minutes, thelayers wereallowed to stand, the organic phase was retained, and the toluene solvent was evaporated to give 816 g of Intermediate 2.

References: [1]Tetrahedron Letters,2019,vol. 60.
[2]Analytical Chemistry,1984,vol. 56,p. 2038 - 2043.
[3]Patent: CN109535081,2019,A .Location in patent: Paragraph 0060; 0063; 0064.

10
[ 58656-98-7 ]
(S)-(-)-3-(dimethylamino)pyrrolidine [ No CAS ]
[ 953434-87-2 ]

Yield	Reaction Conditions	Operation in experiment
42%		Example 8a; (S)-7V-(2-Amino-5-(thiophen-2-yl)phenyl)-4-(3-(dimethylamino)pyrrolidin-l-yl)benzamide(101); Step 1 : (S)-tert-Butyl 4-(3-(dimethylamino)pyrrolidin-l-yl)benzoate (98); [0716] A mixture of fluoride 97 (2.196 g, 11.2 mmol) and (S)-N,JV-dimethylpyrrolidin-3- amine (1.369 g, 11.99 mmol) was stirred at 140 0C under nitrogen atmosphere for 3 h then diluted with DCM, washed with saturated NaHCO3, dried over MgSO4, filtered and <n="102"/>concentrated. The crude compound was purified by flash chromatography (eluent: 50% AcOEt in DCM then 50% isopropanol in DCM with 0.1% triethylamine) to give title compound 98(1.36 g, 42% yield).[0717] 1H NMR (DMSO-de) delta (ppm): 7.67 (d, J= 9.0 Hz, 2H), 6.52 (d, J= 9.0 Hz, 2H), 3.50(dd, J= 9.8, 7.2 Hz, IH), 3.45 to 3.39 (m, IH), 3.30 to 3.24 (m, IH), 3.06 (t, J= 8.2 Hz, IH), 2.83 to 2.75 (m, IH), 2.20 (s, 6H), 2.17 to 2.14 (m, IH), 1.86 to 1.76 (m, IH), 1.51 (s, 9H).

References: [1]Patent: WO2007/118137,2007,A1 .Location in patent: Page/Page column 100-101.

11
[ 5049-61-6 ]
[ 58656-98-7 ]
4-(pyrazin-2-ylamino)-benzoic acid tert-butyl ester [ No CAS ]
4-fluoro-N-pyrazin-2-yl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 80℃; for 18h;	Pyrazin-2-ylamine (475 mg, 5.0 mmol), <strong>[58656-98-7]4-fluorobenzoic acid tert-butyl ester</strong> (981 mg, 5.0 mmol) and potassium tert-butoxide (6.0 mL at 1.0 M in THF, 6.0 mmol) were combined in dry DMF (5 mL) and heated to 80 C. for 18 h. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was triturated with ether/hexane. The solid by-product was filtered off and the filtrate concentrated and the residue chromatographed yielding 252 mg (17%, adjusted for presence of side product) of the title compound as a yellow solid contaminated with 20% of 4-fluoro-N-pyrazin-2-yl-benzamide.

References: [1]Patent: US2008/76771,2008,A1 .Location in patent: Page/Page column 25.

12
[ 4122-04-7 ]
[ 58656-98-7 ]
C₁₄H₁₆N₄O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5447 - 5454.

13
[ 5049-61-6 ]
[ 58656-98-7 ]
4-(pyrazin-2-ylamino)-benzoic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5447 - 5454.

14
[ 109-12-6 ]
[ 58656-98-7 ]
C₁₅H₁₇N₃O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5447 - 5454.

15
[ 591-55-9 ]
[ 58656-98-7 ]
[ 881402-02-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5447 - 5454.

16
[ 58656-98-7 ]
[ 94930-27-5 ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1241 - 1250.
[2]Journal of Organic Chemistry,1985,vol. 50,p. 1010 - 1014.

17
[ 58656-98-7 ]
[ 154535-14-5 ]