152120-61-1|N-Boc-1-Guanylpyrazole| Ambeed

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Quality Control of [ 152120-61-1 ] Purity: 98% SDS Specification

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Product Details of [ 152120-61-1 ]

CAS No. :	152120-61-1
Formula :	C₉H₁₄N₄O₂
M.W :	210.23
SMILES Code :	O=C(OC(C)(C)C)NC(N1N=CC=C1)=N
MDL No. :	MFCD00216663

Safety of [ 152120-61-1 ]

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

Computational Chemistry of [ 152120-61-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	5
Fraction Csp3	0.44
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	55.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	82.5 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
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	1.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.98
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.	0.88
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	-0.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.1
Solubility	1.68 mg/ml ; 0.00801 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.	-2.88
Solubility	0.276 mg/ml ; 0.00131 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	-1.05
Solubility	18.7 mg/ml ; 0.0889 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	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.	-6.49 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	2.0 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)	2.77

Application In Synthesis of [ 152120-61-1 ]

* 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 [ 152120-61-1 ]

[ 152120-61-1 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 4023-02-3 ]
[ 152120-61-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In water; acetone; at 20℃;	To a solution of di-tert-butyldicarbonate (13.4 g, 61.5 mmol) in acetone (45 mL) were added lH-pyrazole-l-carboxamidine hydrochloride (9.0 g, 61.5 mmol, 1.0 equiv.) and 9.0 mL of water. K2CO3 (4.24 g, 30.6 mmol, 0.5 equiv.) in H20 (12.0 mL) was added dropwise for 30 min at room temperature. After 2 h, another portion of di-tert- butyldicarbonate (1.35 g, 6 mmol, 0.1 equiv.) was added and the solution was stirred overnight. The acetone was removed under reduced pressure and the resulting white solid was dissolved in 30.0 mL of water, and allowed to stir at 0 C for 30 min. The precipitated tert-butyl (imino(lH-pyrazol-l-yl)methyl)carbamate was collected by filtration, washed with water, washed with hexane, and dried in vacuo to provide the title compound as a colorless solid (11.37 g, 88% yield). FontWeight="Bold" FontSize="10" H NMR (CDCI3, 400 MHz): delta 9.06 (brs, 1H), 8.45 (d, J= 3.2 Hz, 1H), 7.67 (d, J= 0.8 Hz, 1H), 7.59 (brs, 1H), 6.39 (dd, J = 2.8, 1.6 Hz, 1H), 1.54 (s, 9H).
74.8%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 20h;	Step 1: Preparation of tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate To a solution of (Boc)2O (61 g, 0.28 mol) in THF (1 L) was added DMAP (17 g, 0.14 mol) and Et3N (42 g, 0.42 mol). After stirring for 30 min, 1H-pyrazole-1-carboximidamide hydrochloride (20 g, 0.14 mol) was added and the mixture was stirred at 20 C. for 20 hrs. The reaction was then concentrated in vacuo and the residue was dissolved in EtOAc (500 mL). The solution was washed with aq. NH4Cl (250 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from EtOAc (200 mL) to afford the title compound (22 g, 74.8% yield) as white solid that was used as-is in the next step.
	With N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; ethyl acetate;	Step 1 Manufacture of N-tert-butoxycarbonyl-pyrazole-1-carboxamidine To a solution of di-tert-butyl dicarbonate (7.43 g, 33 mmol) in 100 ml dichloromethane 11.3 ml of N,N-diisopropylethylamine (66 mmol) and 4.40 g of 1H-pyrazole-1-carboxamidine hydrochloride (30 mmol) were added. The solution was agitated for 3 h at room temperature and then evaporated to dryness. The obtained white solid was dissolved in 200 ml ethylacetate, the organic phase was washed with 5 % (w/w) sodium hydrogen carbonate, dried over magnesium sulfate and finally evaporated to dryness. The residue was dissolved in boiling hexane. The solution was allowed to stand at room temperature over night and then at 4C for 24 hours. The crystals thus formed were recovered by filtration and washed in cold hexane (0C). After drying, 5.28 g of white crystals were obtained (25 mmol yield=84 %).

References: [1]Tetrahedron Letters,2007,vol. 48,p. 2357 - 2359.
[2]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3943 - 3948.
[3]Patent: WO2015/147950,2015,A2 .Location in patent: Page/Page column 38.
[4]Patent: US2013/79324,2013,A1 .Location in patent: Paragraph 0827; 0828.
[5]Tetrahedron Letters,1993,vol. 34,p. 3389 - 3392.
[6]Tetrahedron,2007,vol. 63,p. 9502 - 9513.
[7]Patent: EP945138,1999,A1 .

2
[ 24424-99-5 ]
[ 152120-61-1 ]
[ 152120-54-2 ]

Yield	Reaction Conditions	Operation in experiment
73.8%		Step F-2: tert-Butyl ( tert-butoxycarbonyliminopyrazol-1- yl-methyl)carbamate [compound (H)]A tetrahydrofuran (100 ml) solution of the compound (50 g) obtained in Step B-I was added to a tetrahydrofuran (100 ml) suspension of 60% sodium hydride (9.99 g) over 1 hour while maintaining the temperature in the range of -5C to 00C. After the mixture was stirred for 30 minutes at the same temperature, a tetrahydrofuran (100 ml) solution of ditert-butyl dicarbonate (57.1 g) was added while maintaining the temperature from -5C to 00C. and then tetrahydrofuran (250 ml) was added. After the reaction solution was stirred for 2 hours under reflux, acetic acid (20.4 ml) was added at room temperature, and the solvent was distilled off under reduced pressure until the amount of solution became approximately 150 ml. A 5% aqueous sodium hydrogencarbonate solution (500 ml) was added to the resulting solution and the mixture was extracted with ethyl acetate (500 <n="81"/>ml). The organic layer was washed with water (150 ml), and the solvent was distilled off until the amount of solution became approximately 75 ml. Hexane (200 ml) was added to the residue at room temperature, and seed crystal was inoculated. After stirring the solution for 40 minutes under ice-cooling, crystals were filtered, washed with hexane (50 ml), and dried under reduced pressure to give the title compound (54.47 g, 73.8% yield) .1H NMR (CDCl3, 500 MHz): 1.49 (9H, s), 1.55 (9H, s), 6.41 (IH, dd, J = 1.5, 2.7 Hz), 7.62 (IH. dd, J = 0.7, 1.5 Hz), 8.30 (IH, dd, J = 0.7. 2.7 Hz), 8.93 (IH, brs) .13C NMR (CDCl3, 125 MHz): 28.1, 28.2, 81.4, 83.4, 109.8, 129.0. 139.2, 142.8. 149.4, 157.4.

References: [1]Patent: WO2008/126943,2008,A2 .Location in patent: Page/Page column 79-80.
[2]Synthesis,2004,p. 1655 - 1663.
[3]Tetrahedron Letters,1993,vol. 34,p. 3389 - 3392.
[4]Synthetic Communications,1993,vol. 23,p. 3055 - 3060.

3
[ 24424-99-5 ]
[ 4023-00-1 ]
[ 152120-61-1 ]

References: [1]Synthetic Communications,1993,vol. 23,p. 3055 - 3060.

4
[ 24424-99-5 ]
1H-pyrazole-1-carboxamidine nitrate [ No CAS ]
[ 152120-61-1 ]

References: [1]Synthesis,2004,p. 1655 - 1663.

5
[ 107-10-8 ]
[ 152120-61-1 ]
N-tert-butoxycarbonyl-N'-(propyl)guanidine [ No CAS ]