614731-04-3|1-Boc-4-fluoro-4-piperidinecarboxylic Acid| Ambeed

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Quality Control of [ 614731-04-3 ] Purity: 98% SDS Specification

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Product Details of [ 614731-04-3 ]

CAS No. :	614731-04-3
Formula :	C₁₁H₁₈FNO₄
M.W :	247.26
SMILES Code :	CC(C)(C)OC(=O)N1CCC(F)(CC1)C(O)=O
MDL No. :	MFCD08062530
InChI Key :	NRQOTEPIFSRDMH-UHFFFAOYSA-N
Pubchem ID :	21050397

Safety of [ 614731-04-3 ]

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

Computational Chemistry of [ 614731-04-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	0
Fraction Csp3	0.82
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	63.26
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.07
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	1.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.85
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.	1.17
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	0.93
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.99
Solubility	2.52 mg/ml ; 0.0102 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.	-2.41
Solubility	0.967 mg/ml ; 0.00391 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	-1.15
Solubility	17.4 mg/ml ; 0.0705 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.	-6.81 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.	0.56

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)	2.27

Application In Synthesis of [ 614731-04-3 ]

* 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 [ 614731-04-3 ]

[ 614731-04-3 ] Synthesis Path-Downstream 1~35

1
[ 614731-04-3 ]
[ 6638-79-5 ]
[ 614730-11-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; water; ethyl acetate;	Production Example 94 N-methoxy-N-methyl-1-(tert-butoxycarbonyl)-4-fluoropiperidine-4-carboxamide After dissolving 2.19 g of <strong>[614731-04-3]1-(tert-butoxycarbonyl)-4-fluoropiperidine-4-carboxylic acid</strong> in 30 ml of dichloromethane, 2.16 g of 1, 1'-carbonyldimidazole was added and the mixture was stirred at room temperature for 1.5 hours. Next, 1.30 g of N-methyl-O-methylhydroxylamine hydrochloride was added and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The organic layer was washed Withl aqueous sodium carbonate solution, water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (2.33 g, 90% yield). 1H-NMR (400 MHz, CDCl3); delta (ppm) 1.46 (9H, s), 1.93-2.14 (4H, mn), 3.04-3.18 (2H, m), 3.23 (3H, s), 3.72 (3H, s), 3.86-4.0$ (2H, m).

References: [1]Patent: US2004/167224,2004,A1 .

2
[ 614731-04-3 ]
[ 1048993-80-1 ]
N-(1-((5-chloro-2-phenyl-benzofuran-7-yl)methyl)-5-methyl-1H-pyrazol-3-yl)-4-fluoro-4-piperidinecarboxamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example 53 (E53) <n="93"/>lambda/-f1-f(5-Chloro-2-phenyl-1-benzofuran-7-yl)methvn-5-methyl-1H-pyrazol-3-yl)-4- fluoro-4-piperidinecarboxamide hydrochlorideSolution of 1-[(5-chloro-2-phenyl-1-benzofuran-7-yl)methyl]-5-methyl-1 H-pyrazol-3-amine (0.050 g, 0.15 mmol) in dry DCM (1.0 ml) was stirred at room temperature under argon. 1- [(1 ,1-dimethylethyl)oxy]carbonyl}-4-fluoro-4-piperidinecarboxylic acid (0.037 g, 0.15 mmol), EDAC (0.028 g, 0.15 mmol) and HOBt (0.020 g, 0.15 mmol) were added and the solution stirred at room temperature overnight. After this time, the solution was diluted with DCM and the organics were washed with water. Organics were dried over MgSO4, filtered and concentrated under reduced pressure to give a pale yellow oil. The residue was purified [SiO2, EtOAc:Hex 50-100%] to give the title compound. The compound was further purifed using MDAP and the sample treated with MsOH to remove the Boc group. (12 mg) LC/MS Rt = 2.56 min, [M+H]+ 467, 469.

References: [1]Patent: WO2008/98978,2008,A2 .Location in patent: Page/Page column 91-92.

3
[ 1048994-21-3 ]
[ 614731-04-3 ]

Yield	Reaction Conditions	Operation in experiment
		Description 1 (DD 1-fr(1.1-Dimethylethyl)oxy1carbonyl)-4-fluoro-4-piperidinecarboxylic acid <n="34"/>Solution of 4-fluoro-1-(1 ,1-dimethylethyl)-1 ,4-piperidine dicarboxylic acid -4-methyl ester (1.00 g, 4.02 mmol) in EtOH (16 ml) was stirred at room temperature. 2M NaOH (5.0 ml, 10.05 mmol) was added and the solution heated to 60 0C for 5 % hours. After this time, the solution was left to cool to room temperature overnight. The solution was then acidified using 2M HCI and the organics were extracted into EtOAc (x 2). The combined organics were dried over MgSO4, filtered and concentrated under reduced pressure to give a white coloured solid (0.767 g)

References: [1]Patent: WO2008/98978,2008,A2 .Location in patent: Page/Page column 32-33.

4
[ 614731-04-3 ]
[ 1215121-83-7 ]
[ 1215121-85-9 ]

Yield	Reaction Conditions	Operation in experiment
58%		Step 5 To a stirred solution of 16d (0.29 g, 1.173 mmol) in 10 mL of CH2Cl2 was added oxalyl chloride (0.12 mL, 1.38 mmol) followed by a catalytic amount of DMF. The mixture was stirred at room temperature for 1.5 h. Triethylamine (0.4 mL, 2.87 mmol) was added. A solution of 30g (0.34 g, 1.347 mmol) in 2 mL of CH2Cl2 was added. The reaction mixture was allowed to stir for 2.5 days, then was diluted with CH2Cl2 (50 mL), washed with a 1.0 M HCl aqueous solution and brine, dried over Na2SO4, and concentrated in vacuo to provide an oily solid residue. The residue was dissolved in 10 mL of CH2Cl2 and 2 mL of trifluoroacetic acid and allowed to stir for 5 hours, then concentrated in vacuo. The residue obtained was dissolved in 50 mL of CH2Cl2, washed with a saturated NaHCO3 aqueous solution and brine.The organic solution was dried, and concentrated to provide a crude oil, which was purified using preparative TLC (CH2Cl2-7N NH3 in MeOH=25:1, v/v) to provide compound 30h (260 mg, 58%, MH+=382.2).

References: [1]Patent: US2011/166124,2011,A1 .Location in patent: Page/Page column 46.

5
[ 614731-04-3 ]
[ 72081-99-3 ]
C₂₁H₂₃FN₄O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5274 - 5282.

6
[ 614731-04-3 ]
[ 614730-97-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 5h;	1-(tert-Butoxycarbonyl)-4-fluoropiperidine-4-carboxylic acid 13a (5.0 g, 20 mmol) was dissolved in 50 mL of THF.A borane tetrahydrofuran solution (50 mL, 1 M/THF) was added dropwise at 0 C, and the mixture was reacted at room temperature for 5 hours. Slow down in the reaction solution at 0 CThe reaction was quenched by slowly adding 20 mL of methanol. Concentrate under reduced pressure to remove the solvent. Add 50 mL of water and extract with ethyl acetate (50 mL×3).The combined organic layers were washed with EtOAc EtOAc (EtOAc)Fluor-4-(hydroxymethyl)piperidine-1-carboxylic acid tert-butyl ester 13b (4.7 g, colorless oil), yield: 100%.
98%	With borane-THF; In tetrahydrofuran; for 32h;Reflux;	To a solution of 1- (tert-butoxycarbonyl) -4-fluoropiperidine-4-carboxylic acid (5.00 g, 20.20 mmol) in tetrahydrofuran (100 mL) was added a solution of borane tetrahydrofuran complex (30.3 mL, 30.30 mmol, 1.0 M solution in tetrahydrofuran) . The reaction mixture was refluxed for 16 hours, and then another 24 mL of borane tetrahydrofuran complex was added and continued to reflux for another 16 hours. After cooling to ambient temperature the reaction mixture poured onto ice-cold water (50 mL) and saturated ammonium chloride (100 mL) , and extracted with ethyl acetate (3 x 100 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (4.60 g, 98) . Which was used in the next step without further purification: MS (ES+) m/z 234.1 (M +1) .
	With borane-THF; In tetrahydrofuran; for 32h;Reflux; Inert atmosphere;	Step 1. Preparation of tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (0341) <strong>[614731-04-3]1-(tert-butoxycarbonyl)-4-fluoropiperidine-4-carboxylic acid</strong> (5.00 g, 20.20 mmol) in tetrahydrofuran (100 mL) was added a solution of borane tetrahydrofuran complex (30.3 mL, 30.30 mmol, 1.0 M solution in tetrahydrofuran). The reaction mixture was refluxed for 16 hours, and then another 24 mL of borane tetrahydrofuran complex was added and continued to reflux for another 16 hours. After cooling to ambient temperature the reaction mixture poured onto ice-cold water (50 mL) and saturated ammonium chloride (100 mL), and extracted with ethyl acetate (3×100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (4.60 g, 98%). Which was used in the next step without further purification: MS (ES+) m/z 234.1 [M+H]+.

References: [1]Patent: CN109574927,2019,A .Location in patent: Paragraph 0465; 0467-0470.
[2]Patent: WO2015/78374,2015,A1 .Location in patent: Page/Page column 415.
[3]Patent: US2016/340309,2016,A1 .Location in patent: Paragraph 0341; 0342.

7
[ 614731-04-3 ]
tert-butyl 4-((4-(tert-butoxycarbonyl)-2-chloro-5-fluorophenoxy)methyl)-4-fluoropiperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/78374,2015,A1 .
[2]Patent: US2016/340309,2016,A1 .

8
[ 614731-04-3 ]
tert-butyl 4-((4-(tert-butoxycarbonyl)-2-cyclopropyl-5-fluorophenoxy)methyl)-4-fluoropiperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/78374,2015,A1 .

9
[ 614731-04-3 ]
tert-butyl 5-cyclopropyl-2-fluoro-4-((4-fluoropiperidin-4-yl)methoxy)benzoate hydrochloride [ No CAS ]

References: [1]Patent: WO2015/78374,2015,A1 .

10
[ 614731-04-3 ]
tert-butyl 4-((1-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-4-fluoropiperidin-4-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate [ No CAS ]

References: [1]Patent: WO2015/78374,2015,A1 .

11
[ 614731-04-3 ]
4-((1-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-4-fluoropiperidin-4-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid [ No CAS ]

References: [1]Patent: WO2015/78374,2015,A1 .

12
[ 614731-04-3 ]
[ 918431-92-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		A solution of <strong>[614731-04-3]1-boc-4-fluoro-4-piperidinecarboxylic acid</strong> (300 mg, 1.15 mmol) in ethylene glycol dimethyl ether (15 mL) was treated with 4-methylmorpholine (0.13 mL, 1.15 mmol) and isopropyl chloroformate (1 M solution in toluene, 1.38 mL, 1.38 mmol) at -15C. After stirring for 10 mm, ammonia solution (0.5 M in dioxane, 3.50 mL, 1.75 mmol) was added.The reaction mixture was stirred at RT for 18h. The solvents were evaporated under reduced pressure, the crude product was dissolved in EtOAc, washed with 1 N NaOH solution, water and brine and the organic layers were dried over sodium sulfate, filtered and evaporated to dryness to get 185 mg (65 %) of a white powder. The product was used for the next step without further purification. LCIMS (Method A): Rt = 1.79 mm,(M+H) 173.
90%	With ammonium chloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 25℃;	tert-Butyl 4-carbamoyl-4-fluoropiperidine-1-carboxylate (0414) In a 250-mL round-bottom flask were combined <strong>[614731-04-3]1-[(tert-butoxy)carbonyl]-4-fluoropiperidine-4-carboxylic acid</strong> (3 g, 12.13 mmol, 1.00 equiv), DMF (50 mL), NH4Cl (1.75 g, 32.72 mmol, 1.50 equiv), HATU (9.23 g, 24.27 mmol, 2.00 equiv), and iPr2NEt (3.13 g, 24.22 mmol, 2.00 equiv). The resulting solution was stirred overnight at 25 C. The resulting solution was extracted with 200 mL of EtOAc and the organic layers were combined, washed with 5×50 mL of H2O, then applied onto a silica gel column with ethyl acetate/petroleum ether, affording 2.7 g (90%) of the product as a white solid.

References: [1]Patent: WO2015/144290,2015,A1 .Location in patent: Page/Page column 82.
[2]Patent: US2016/237043,2016,A1 .Location in patent: Paragraph 0413; 0414.

13
[ 614731-04-3 ]
[ 918431-93-3 ]

References: [1]Patent: US2016/237043,2016,A1 .

14
[ 614731-04-3 ]
4-fluoropiperidine-4-carbonitrile [ No CAS ]

References: [1]Patent: US2016/237043,2016,A1 .

15
[ 614731-04-3 ]
C₃₂H₃₅F₂N₇O₂ [ No CAS ]

References: [1]Patent: US2016/237043,2016,A1 .

16
[ 614731-04-3 ]
N-(6-bromo-3-isoquinolyl)-4-fluoro-piperidine-4-carboxamide [ No CAS ]

References: [1]Patent: US2017/313681,2017,A1 .

17
[ 614731-04-3 ]
N-(6-bromo-3-isoquinolyl)-4-fluoro-1-isobutyl-piperidine-4-carboxamide [ No CAS ]

References: [1]Patent: US2017/313681,2017,A1 .

18
[ 891785-28-7 ]
[ 614731-04-3 ]
tert-butyl 4-[(6-bromo-3-isoquinolyl)carbamoyl]-4-fluoro-piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.7%		Step 1 To a mixture of <strong>[614731-04-3]1-tert-butoxycarbonyl-4-fluoro-piperidine-4-carboxylic acid</strong> (XXXVIII) (1.07 mL, 13.99 mmol), HATU (7.09 g, 18.65 mmol) and DIPEA (4.87 mL, 27.97 mmol) in DMF (40 mL) was stirred for 10 min. Then, 6-bromoisoquinolin-3-amine (XII) (2.08 g, 9.32 mmol) and DMAP (0.23 g, 1.86 mmol) was added then the mixture was heated to 80 C. overnight. The reaction mixture was concentrated, the residue partitioned between EtOAc/sat.NaHCO3, organic layer separated, washed with water and brine. The organics were then separated and dried (MgSO4) before concentration to dryness. The crude was then purified by flash column chromatography (0?40% EtOAc/hexanes). The desired fractions were concentrated to dryness en vacuo and recrystallized with hexanes to obtain tert-butyl 4-[(6-bromo-3-isoquinolyl)carbamoyl]-4-fluoro-piperidine-1-carboxylate (XXXIX) (2.94 g, 6.50 mmol, 69.7% yield) as a white solid. ESIMS found for C20H23BrFN3O3 m/z 452.1 (79BrM+1).

References: [1]Patent: US2017/313681,2017,A1 .Location in patent: Paragraph 0843; 0844.

19
[ 614731-04-3 ]
N-(6-(2H-1,2,3-triazol-2-yl)isoquinolin-3-yl)-4-fluoro-1-isobutylpiperidine-4-carboxamide [ No CAS ]
N-(6-(1H-1,2,3-triazol-1-yl)isoquinolin-3-yl)-4-fluoro-1-isobutylpiperidine-4-carboxamide [ No CAS ]

References: [1]Patent: US2017/313681,2017,A1 .

20
[ 614731-04-3 ]
methyl 5-cyclopropyl-2-fluoro-4-(((4-fluoropiperidin-4-yl)methoxy)methyl)benzoate [ No CAS ]