174855-57-3|1-Boc-4-(2-Formylphenyl)piperazine| Ambeed

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Quality Control of [ 174855-57-3 ] Purity: 95% SDS Specification

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Product Details of [ 174855-57-3 ]

CAS No. :	174855-57-3
Formula :	C₁₆H₂₂N₂O₃
M.W :	290.36
SMILES Code :	C2=C(N1CCN(C(OC(C)(C)C)=O)CC1)C(=CC=C2)C=O
MDL No. :	MFCD05864664
InChI Key :	FGJACYJASSSXNJ-UHFFFAOYSA-N
Pubchem ID :	6490990

Safety of [ 174855-57-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 174855-57-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	89.03
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.85 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.98
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	2.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.79
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.	1.53
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	1.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.89
Solubility	0.375 mg/ml ; 0.00129 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.	-2.85
Solubility	0.41 mg/ml ; 0.00141 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	-3.02
Solubility	0.277 mg/ml ; 0.000953 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	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.	-6.53 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	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<0.0
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)	2.31

Application In Synthesis of [ 174855-57-3 ]

* 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 [ 174855-57-3 ]

[ 174855-57-3 ] Synthesis Path-Downstream 1~35

1
[ 33966-50-6 ]
[ 174855-57-3 ]
4-[2-(sec-butylamino-methyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.

2
[ 5813-64-9 ]
[ 174855-57-3 ]
4-{2-[(2,2-dimethyl-propylamino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.

3
[ 78-81-9 ]
[ 174855-57-3 ]
4-[2-(isobutylamino-methyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.

4
[ 75-04-7 ]
[ 174855-57-3 ]
4-(2-ethylaminomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.

5
[ 446-52-6 ]
[ 57260-71-6 ]
[ 174855-57-3 ]

Yield	Reaction Conditions	Operation in experiment
42.7%	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 4.0h;Inert atmosphere;	Put 2-fluorobenzaldehyde (4.0g, 32.2mmol),Piperazine-tert-butyl formate (6.6 g, 35.4 mmol) was added to DMSO (96 mL), followed by potassium carbonate (6.4 g, 64.4 mmol). The reaction was heated to 130 C. for 4 hours under nitrogen protection. The reaction was stopped and cooled to room temperature. The reaction solution was quenched with water (100 mL), extracted with ethyl acetate (60 mL × 3), and the organic phase was collected, washed with water and saturated brine in sequence, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was subjected to silica gel chromatography. Column (petroleum ether: ethyl acetate (V: V) = 10: 1) was further purified to give the title compound (light yellow solid, 4.0 g, 42.7%).
8.5 g	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 12.0h;	To a solution of 2-fluorobenzaldehyde (13.33 g, 107.38 mmol) and tert-butyl piperazine-1-carboxylate (30.0 g, 161.07 mmol) in DMSO (150 mL) was added K 2CO 3 (44.52 g, 322.15 mmol). The mixture was stirred at 100C for 12 hr. TLC indicated the reactant was consumed completely. The reaction mixture was cooled to room temperature and poured into H 2O (150 mL) and extracted with EA (150 mL 3), dried over Na 2SO 4, filtered and concentrated. The residue was purified by column chromatography (Silica gel, PE/EA=100/1 to 30/1). Tert-butyl 4- (2-formylphenyl) piperazine-1-carboxylate (8.5 g) was obtained as a yellow solid. 1H NMR (400MHz, CDCl 3) δ ppm: 1.50 (s, 9 H), 3.02 -3.08 (m, 4 H), 3.61 -3.66 (m, 4 H), 7.11 (d, J=8.2 Hz, 1H), 7.17 (t, J=7.5 Hz, 1H), 7.52 -7.58 (m, 1H), 7.83 (dd, J=7.7, 1.8 Hz, 1H), 10.36 (s, 1H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4417 - 4423.
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 6821 - 6830.
[4]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.
[5]Synthesis,2010,p. 4287 - 4299.
[6]Patent: CN108299338,2018,A .Location in patent: Paragraph 0142; 0144; 0145; 0146; 0147.
[7]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5605 - 5609.
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4817 - 4822.
[9]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604.
[10]Patent: WO2019/210828,2019,A1 .Location in patent: Paragraph 0347; 0348; 0349.

6
[ 616-24-0 ]
[ 174855-57-3 ]
4-{2-[(1-ethyl-propylamino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.

7
[ 174855-57-3 ]
[ 179250-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 2.0h;	Dissolve tert-butyl 4- (2-formylphenyl) piperazine-1-carboxylate (4.0 g, 13.8 mmol) in methanol (69 mL),Sodium borohydride (0.87 g, 20.7 mmol) was added at 0 C. After the addition was completed, the reaction was carried out at room temperature for 2 hours. Stop reactionIt was quenched with water and extracted with dichloromethane. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.The obtained crude product was further purified by a silica gel chromatography column (petroleum ether: ethyl acetate (V: V) = 5: 1) to obtain the title compound.(Light yellow solid, 3.6 g, 89%).
1.1 g (95%)	With hydrogenchloride; sodium tetrahydroborate; In methanol; ethyl acetate;	Step B: 1-t-Butoxycarbonyl-4-(2-hydroxymethylphenyl)-piperazine A solution of 1.15 g (3.96 mmol) of 1-t-butoxycarbonyl-4-(2-formyl-phenyl)-piperazine in 10 mL of MeOH was treated with 0.15 g (3.96 mmol) of NaBH4. After 2 h the reaction was quenched by adding 1.2N HCl and the mixture was extracted with EtOAc. The EtOAc solution was washed with water, brine and dried. The filtrate was concentrated to yield 1.1 g (95%) of 1-t-butoxycarbonyl-4-(2-hydroxymethyl-phenyl)-piperazine as a white foam which was used without purification. 1 H NMR (CDCl3) δ 1.24 (s, 9H), 2.92 (m, 4H), 3.59 (m, 4H), 4.84 (s, 2H), 7.0-7.4 (m, 4H).

References: [1]Patent: CN108299338,2018,A .Location in patent: Paragraph 0142; 0148; 0149; 0150; 0151.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796.
[3]Patent: US5607936,1997,A .
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4817 - 4822.

8
[ 123-75-1 ]
[ 174855-57-3 ]
[ 444581-99-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

9
[ 110-89-4 ]
[ 174855-57-3 ]
[ 444582-62-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

10
[ 616-47-7 ]
[ 174855-57-3 ]
[ 444582-74-5 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

11
[ 24424-99-5 ]
[ 736991-52-9 ]
[ 174855-57-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

12
[ 142-84-7 ]
[ 174855-57-3 ]
[ 668980-38-9 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

13
[ 109-89-7 ]
[ 174855-57-3 ]
[ 444582-64-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755.

14
[ 174855-57-3 ]
[ 736991-52-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4417 - 4423.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5605 - 5609.
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 6821 - 6830.
[4]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4615 - 4618.

15
[ 343338-28-3 ]
[ 174855-57-3 ]
[ 869478-17-1 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.

16
[ 174855-57-3 ]
4-{2-[(S)-2-methyl-1-((S_S)-2-methyl-propane-2-sulfinylamino)-propyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.

17
[ 174855-57-3 ]
4-{2-[(R)-2-methyl-1-((S_S)-2-methyl-propane-2-sulfinylamino)-propyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.

18
[ 174855-57-3 ]
4-{2-[(S)-3-methyl-1-((S_S)-2-methyl-propane-2-sulfinylamino)-butyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.

19
[ 174855-57-3 ]
4-{2-[(R)-3-methyl-1-((S_S)-2-methyl-propane-2-sulfinylamino)-butyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931.

20
[ 174855-57-3 ]
[ 865303-23-7 ]