111669-25-1|1-Boc-4-(3-Aminopyridin-2-yl)piperazine| Ambeed

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Quality Control of [ 111669-25-1 ] Purity: 97% SDS Specification

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Product Details of [ 111669-25-1 ]

CAS No. :	111669-25-1
Formula :	C₁₄H₂₂N₄O₂
M.W :	278.35
SMILES Code :	NC1=CC=CN=C1N2CCN(C(OC(C)(C)C)=O)CC2
MDL No. :	MFCD03407996
InChI Key :	CBTYZJKYXVDWOG-UHFFFAOYSA-N
Pubchem ID :	2756375

Safety of [ 111669-25-1 ]

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

Computational Chemistry of [ 111669-25-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	6
Fraction Csp3	0.57
Num. rotatable bonds	6
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	85.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.69 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.85
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	1.55
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.97
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.	0.98
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	0.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.37
Solubility	1.19 mg/ml ; 0.00428 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.	-2.67
Solubility	0.602 mg/ml ; 0.00216 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	-2.74
Solubility	0.51 mg/ml ; 0.00183 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	No
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	Yes
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.	-6.9 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	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<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)	2.74

Application In Synthesis of [ 111669-25-1 ]

* 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 [ 111669-25-1 ]

[ 111669-25-1 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 87394-62-5 ]
[ 111669-25-1 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1145 - 1151.

2
[ 111669-25-1 ]
[ 75-07-0 ]
[ 111669-26-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium cyanoborohydride; In methanol; at 20℃; for 48h;	Example 34.1 : 4-(3-Ethylamino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester. To a mixture of 4-(3-amrno-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2,0 g, 7.18 mmol), acetaldehyde (0.81 mL, 0.014 mol) and methanol (30 mL) was added sodium cyanoborohydride (1.36 g, 0.022 mol). The reaction mixture was stirred at room temperature for 2 days and then diluted with ethyl acetate, washed with water and washed with brine. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel using hexanes: ethyl acetate (80:20) to give 4-(3-ethylamino-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2.0 g, 91 %). GC/MS mfz 306, 223, 162, 150, 137, 120, 57.

References: [1]Patent: WO2008/112440,2008,A1 .Location in patent: Page/Page column 46-47.
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 1145 - 1151.

3
[ 153473-24-6 ]
[ 111669-25-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 2h;	A mixture of tert-butyl 4-(3-nitropyridin-2-yl)piperazine-l -carboxylate 5 (350 mg, 1.14 mmol), Pd/C (60.4 mg, 10%, 0.0568 mmol) and MeOH (6 ml) was subjected to the hydrogenation condition with hydrogen balloon at room temperature. After stirring for 2 h, the resulting solution was filtered through celite. The resulting organic solution was concentrated under reduced pressure and purified by silica gel column chromatography (Hexane/EtOAc/CH2Cl2 = 1 : 1 : 1) to give tert-butyl 4-(3-aminopyridin-2-yl)piperazine-l -carboxylate (246 mg, 78%) as a white powder. MS (EI) for Ci4H22 402: 279.2 (MH+).
69%	With hydrogen;palladium on activated charcoal; In ethanol; under 1034.32 Torr; for 2h;	Example 18.1: 4-(3-Ammo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester. A mixture of 4-(3-nitro-pyridin-2-yl)-piperazine-l-carboxylic acid tert-tmtyl ester (4.0 g, 12,97 mmol), palladium (on activated carbon, 500 mg) and ethanol (150 mL) was shaken under 20 psi of hydrogen for 2 hours. The reaction mixture was filtered through Diatomaceous earth and concentrated to give 4-(3-amino-pyridin-2-yl)-piperazine-l- carboxylic acid tert-butyl ester (2.5 g, 69 %). GC/MS m/z 278, 205, 134, 148, 109, 93, 57.
	With palladium(II) hydroxide; In methanol; cyclohexene; at 70℃; for 2h;	Synthesis of 3-Amino-2-(Boc-piperazinyl)pyridine 7: 3-Nitro-2-(Boc-piperazine)pyridine 6 (1.765 g, 5.72 mmol) was dissolved in methanol (15 mL) at room temperature. Then Pd(OH)2 (1.234 g) and cyclohexene (2.0 mL, 19.52 mmol) were added. The resulting mixture was heated at 70 C. for 2 h. The mixture was concentrated to remove the solvent. DCM was added and then it was filtered through a pad of silica gel, washed with DCM and 10% MeOH/DCM. The collected solution was concentrated and dried under high vacuum to afford a slight pink solid as the product (1.384 g, 87% yield). 1H-NMR (CDCl3): 7.794 (dd, J=5.0 Hz and 1.5 Hz, 1 H, Ar-H), 6.956 (dd, J=7.5 Hz and 1.5 Hz, 1 H, Ar-H), 6.854 (dd, J=7.5 Hz and 5.0 Hz, 1 H, Ar-H), 3.783 (br, 2 H, NH2), 3.571 (t, J=4.5-5.0 Hz, 4 H, 2 CH2), 3.059 (t, J=4.5-5.0 Hz, 4 H, 2 CH2), 1.482 (s, 9 H, 3 CH3). LC-MS: 279.2 (MH+). (ref. Romero D. L. et al. J. Med. Chem. 37, 999-1014, 1994.) Synthesis of 2-(Boc-piperazinyl)-3-(isopropylamino)pyridine 4:

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 999 - 1014.
[2]Patent: WO2012/61337,2012,A1 .Location in patent: Page/Page column 45.
[3]Patent: WO2008/112440,2008,A1 .Location in patent: Page/Page column 38-39.
[4]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1406 - 1411.
[5]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 363 - 366.
[6]Patent: US9226970,2016,B2 .Location in patent: Page/Page column 28.

4
[ 116-11-0 ]
[ 111669-25-1 ]
<2-<1-(tert-Butyloxycarbonyl)-4-piperazinyl>pyridin-3-yl>(1-methylethylidene)amine [ No CAS ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 2642 - 2644.

5
[ 111669-25-1 ]
[ 67-64-1 ]
[ 136818-14-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		3-amino-2-(Boc-piperazine)pyridine 7 (3.813 g, about 11.16 mmol, crude) was dissolved in dichloroethane (75 mL). Acetone (1.7 mL, 23.12 mmol) was added, followed by an addition of HOAc (1.0 mL, 17.45 mmol) at room temperature. After about 10 min, NaBH(OAc)3 (7.46 g, 33.44 mmol) was added. An additional amount of dichloroethane (25 mL) was added. The resulting mixture was stirred at room temperature for 64 h. 5% aqueous NaHCO3 was added to quench the reaction. The organic phase was separated and the aqueous phase was extracted with dichloromethane (2*50 mL). The combined organic solution was washed with brine, dried over anhydrous Na2SO4, concentrated. The residue was purified via flash column chromatography over silica gel with 5-35% ethyl acetate in hexane to afford the product as solid in quantitative yield. 1H-NMR (CDCl3): 7.673 (dd, J=5.0 Hz and 1.5 Hz, 1 H, Ar-H), 6.904 (dd, J=8.0 Hz and 5.0 Hz, 1 H, Ar-H), 6.812 (dd, J=8.0 Hz and 1.5 Hz, 1 H, Ar-H), 4.150 (d, J=7.5 Hz, 1 H, NH), 3.569-3.517 (m, 5 H, 2CH2 and CH), 2.997 (t, J=5.0 Hz, 4 H, 2 CH2), 1.477 (s, 9 H, 3 CH3), 1.23 (d, J=6.0 Hz, 6 H, 2 CH3). (ref. Romero D. L. et al. J. Med. Chem. 37, 999-1014, 1994.) Synthesis of 2-piperazinyl-3-(isopropylamino)pyridine 8:

References: [1]Patent: US9226970,2016,B2 .Location in patent: Page/Page column 28; 29.
[2]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1406 - 1411.
[3]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 363 - 366.

6
[ 5470-18-8 ]
[ 111669-25-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1406 - 1411.
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 1145 - 1151.
[3]Patent: US9226970,2016,B2 .

7
[ 87394-48-7 ]
[ 111669-25-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1406 - 1411.
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 1145 - 1151.

8
[ 111669-25-1 ]
[ 147539-21-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1406 - 1411.
[2]Patent: US9226970,2016,B2 .

9
[ 111669-25-1 ]
[4-(3-isopropylamino-pyridin-2-yl)-piperazin-1-yl]-(5-phenyl-1H-pyrrol-2-yl)-methanone [ No CAS ]