24835-08-3|(2-Nitrophenyl)methanamine hydrochloride| Ambeed

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Quality Control of [ 24835-08-3 ] Purity: 97% SDS Specification

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Product Details of [ 24835-08-3 ]

CAS No. :	24835-08-3
Formula :	C₇H₉ClN₂O₂
M.W :	188.61
SMILES Code :	NCC1=CC=CC=C1[N+]([O-])=O.[H]Cl
MDL No. :	MFCD00136280
InChI Key :	BASJTVIZZDEQBJ-UHFFFAOYSA-N
Pubchem ID :	12235442

Safety of [ 24835-08-3 ]

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

Computational Chemistry of [ 24835-08-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	49.9
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	1.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.7
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.	0.68
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	0.69

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.37
Solubility	0.807 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.	-2.91
Solubility	0.234 mg/ml ; 0.00124 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	-1.81
Solubility	2.94 mg/ml ; 0.0156 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.	-6.19 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	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)	1.69

Application In Synthesis of [ 24835-08-3 ]

* 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 [ 24835-08-3 ]

[ 24835-08-3 ] Synthesis Path-Downstream 1~35

1
[ 4530-20-5 ]
[ 24835-08-3 ]
N-(tert-Butoxycarbonyl)-N'-(2-nitrobenzyl)glycinamide [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 4599 - 4605.

2
[ 24277-39-2 ]
[ 24835-08-3 ]
N-(tert-Butoxycarbonyl)-N'-(2-nitrobenzyl)-L-glutamine α-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 4599 - 4605.

3
[ 917-61-3 ]
[ 24835-08-3 ]
[ 135963-32-5 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 8827 - 8831.

4
C₄₄H₆₆Br₂N₆O₁₀S₂Si₃ [ No CAS ]
[ 24835-08-3 ]
C₅₀H₆₈Br₂N₈O₁₁SSi₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 12896 - 12900.

5
[ 24835-08-3 ]
[ 532-55-8 ]
C₁₅H₁₃N₃O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6574 - 6595.

6
[ 24835-08-3 ]
N-(2-Nitrobenzyl)glycinamide hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 4599 - 4605.

7
[ 24835-08-3 ]
N-(2-Nitrobenzyl)-L-glutamine hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 4599 - 4605.

8
[ 24835-08-3 ]
[ 532-55-8 ]
[ 630409-82-4 ]

Yield	Reaction Conditions	Operation in experiment
		(a) Preparation of amino([(2-nitrophenyl)methyl]amino)-methane-1-thione.To a solution of <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (Avocado) (4.93 g, 26.1 mmol) and Et3N (10 ML, 71.8 mmol) in CHCl3 (300 ML) was added benzoyl isothiocyanate (Aldrich) (3.4 ML, 25.3 mmol) and the resulting yellow solution was heated to 61 C. After 1.5 h the solvent was removed in vacuo and the residue was dissolved in 70% aqueous MeOH. To the solution was added K2CO3 (4.06 g, 29.4 mmol) and the reaction was heated at reflux for 0.5 h.The yellow-orange mixture was cooled to RT and the crude material was purified by flash chromatography on silica gel with Hexanes:EtOAc (4:1, 1:1, 1:3) as eluant to afford a purple solid. Mp: 228-229 C. MS m/z: 212 (M+1). Calc'd for C8H9N3O2S-211.04.

References: [1]Patent: US2003/229068,2003,A1 .Location in patent: Page 34.

9
[ 24835-08-3 ]
[ 67-64-1 ]
[ 338991-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol; at 0 - 20℃; for 3h;	Example 2; [00281] [N-methyl-N-2-((tert-butoxycarbonylisopropylamino)methyl)phenyl]carbamic acid 1-chloro-ethyl ester [00282]; a) Preparation of Isopropyl-(2-nitro-benzyl)-carbamic acid tert-butyl ester; [00283] To a mixture of <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (500 mg, 2.65 mmol) and acetone (0.39 ml, 5.30 mmol) in methanol (13 ml) was added sodium cyanoborohydride (500 mg, 7.95 mmol) at 0 C. The temperature was warm up to room temperature. After stirring for 3 hr, the mixture was concentrated in vacuo and extracted with dichloromethane. The combined organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give N-isopropyl-2-nitrobenzylamine as yellow oil. This compound was used in next step without further purification. [00284] To a mixture of N-isopropyl-2-nitrobenzylamine and N,N-diisopropylethyl amine (1.15 ml, 6.63 mmol) in tetrahydrofuran (20 ml) was added di-tert-butyl dicarbonate (1.22 ml, 5.30 mmol) at room temperature. After stirring overnight, the mixture was quenched with water and extracted with ethyl acetate. The combined: organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (15% ethyl acetate-hexane) to afford isopropyl-(2-nitro-benzyl)-carbamic acid tert-butyl ester (e) (736 mg, 2.50 mmol, 94%) as light yellow oil.

References: [1]Patent: US6812238,2004,B1 .Location in patent: Page/Page column 21-22; 33.

10
[ 99-61-6 ]
[ 24835-08-3 ]
[ 105-45-3 ]
[ 154026-66-1 ]
dimethyl 2-6-dimethyl-1-(2-nitrobenzyl)-4-(3-nitrophenyl)-1,4-dihyrdo-pyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.7 g (18%)	In pyridine;	Example 1 Dimethyl 2,6-dimethyl-1-(2-nitrobenzyl)-4-(3-nitrophenyl)-1,4-dihydro-pyridine-3,5-dicarboxylate STR16 A mixture of 3 g (20 mmol) 3-nitrobenzaldehyde, 4.6 g (40 mmol) methyl acetoacetate and 3.7 g (20 mmol) 2-nitrobenzylamine HCl in 20 ml pyridine is heated for 6 h under reflux. After cooling the mixture is poured into water, extracted with CH2 Cl2, died and the solvent removed. Chromatography yielded 1.7 g (18%) of dimethyl 2-6-dimethyl-1-(2-nitrobenzyl)-4-(3-nitrophenyl)-1,4-dihyrdo-pyridine-3,5-dicarboxylate (mp: 180 C.).

References: [1]Patent: US5606066,1997,A .

11
[ 24835-08-3 ]
[ 140-88-5 ]
[ 50794-17-7 ]
[ 6057-90-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium sulfate; In ethanol; water;	EXAMPLE 7 Ethyl β-(o-Nitrobenzylamino)-propionate (see J.A.C.S., 80, 1168 (1958) o-Nitrobenzylamine hydrochloride (20.4 g., 0.114 mole) was dissolved in a minimum volume of water and the solution was made strongly basic by addition of 10% sodium hydroxide. The clear oil which formed was extracted into two 120-ml. portions of ether. The ether was dried with 10 g. of anhydrous sodium sulfate, filtered, and finally dried over Drierite. The dried solution was filtered and evaporated, leaving a yellow oil. The oil was dissolved in 100 ml. of absolute ethanol and 11.4 g (0.114 mole) of freshly distilled ethyl acrylate was added. This solution was allowed to stand overnight and the solvent removed by distillation from a steam-cone. The oily residue was dissolved in 200 ml. of dry ether, the solution was cooled in an ice bath, and treated with dry hydrogen chloride. When precipitation was complete, the solid was filtered and dissolved in 120 ml. of boiling absolute ethanol. The hydrochloride crystallized from this solution on cooling yielding 20.7 g. of the aminopropionate hydrochloride, m.p. 137.5-139.0. By concentrating and cooling the mother liquor, an additional 5 g. was obtained, m.p. 136.5-138.5, and by repeating this operation 1.1 g., m.p. 136-139, was obtained, raising the total yield to 26.8 g. (81.4%). The analytical sample was prepared by repeated crystallization from absolute ethanol to give a melting point of 138.5-139.0. Anal. calc'd. for C12 H17 O4 N2 Cl: C, 49.91; H, 5.94; N, 9.70. Found: C, 49.9; H, 5.94; N, 9.51.
	With hydrogenchloride; sodium hydroxide; sodium sulfate; In ethanol; water;	EXAMPLE 7 Ethyl β-(o-Nitrobenzylamino)-propionate (see J.A.C.S., 80, 1168 (1958) o-Nitrobenzylamine hydrochloride (20.4 g., 0.114 mole) was dissolved in a minimum volume of water and the solution was made strongly basic by addition of 10% sodium hydroxide. The clear oil which formed was extracted into two 120-ml. portions of ether. The ether was dried with 10 g. of anhydrous sodium sulfate, filtered, and finally dried over Drierite. The dried solution was filtered and evaporated, leaving a yellow oil. The oil was dissolved in 100 ml. of absolute ethanol and 11.4 g (0.114 mole) of freshly distilled ethyl acrylate was added. This solution was allowed to stand overnight and the solvent removed by distillation from a steam-cone. The oily residue was dissolved in 200 ml. of dry ether, the solution was cooled in an ice bath, and treated with dry hydrogen chloride. When precipitation was complete, the solid was filtered and dissolved in 120 ml. of boiling absolute ethanol. The hydrochloride crystallized from this solution on cooling yielding 20.7 g. of the aminopropionate hydrochloride, m.p. 137.5-139.0. By concentrating and cooling the mother liquor, an additional 5 g. was obtained, m.p. 136.5-138.5, and by repeating this operation 1.1 g., m.p. 136-139, was obtained, raising the total yield to 26.8 g. (81.4%). The analytical sample was prepared by repeated crystallization from absolute ethanol to give a melting point of 138.5-139.0. Anal. calc'd. for C12 H17 O4 N2 Cl: C, 49.91; H, 5.94; N, 9.70. Found: C, 49.9; H, 5.94; N, 9.51. SPC26

References: [1]Patent: US31617,1984,E1 .
[2]Patent: US3932407,1976,A .

12
[ 79099-07-3 ]
[ 24835-08-3 ]
[ 87120-79-4 ]

Yield	Reaction Conditions	Operation in experiment
		31. tert-Butyl 4-r(2-nitrobenzyl)amino1piperidine- 1 -carboxylate; To a mixture of <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (20.0 g, 106.0 mmol) in DCE (250 mL) is added TEA (10.73 g, 106.0 mmol). The mixture is allowed to stir at rt for 5 min. To this mixture N-Boc-4-piperidone (21.13 g, 106.0 mmol), and HOAC (7.96 g, 132.5 mmol), is added and stirred at rt for another 5 min. NaBH(OAc)3 (25.28 g, 119.3 mmol) is added in portions and the mixture is stirred at rt for 1 hr before it is washed with 10 % Na2CO3 solution (100 mL x 3) and brine (50 mL x 2). The organic phase is dried over Na2SO4. The solvent is removed in vacuo to afford the title compound as a red oil, which is used without further purification in subsequent steps.
		18. tert-Butyl 4-r(2-nitrobenzyl)aminolρiρeridine-l -carboxvlate; To a mixture of <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (20.0 g, 106.0 mmol) in DCE (250 mL) is added TEA (10.73 g, 106.0 mmol). The mixture is allowed to stir at rt for 5 min. To this mixture N-Boc-4-piperidone (21.13 g, 106.0 mmol), and HOAC (7.96 g, 132.5 mmol), is added and stirred at rt for another 5 min. NaBH(OAc)3 (25.28 g, 119.3 mmol) is added in portions and the mixture is stirred at rt for 1 hr before it is washed with 10 % Na2CO3 solution (100 mL * 3) <n="59"/>and brine (50 mL x 2). The organic phase is dried over Na2SCU- The solvent is removed in vacuo to afford the title compound as a red oil, which is used without further purification in subsequent steps.

References: [1]Patent: WO2008/60568,2008,A2 .Location in patent: Page/Page column 66.
[2]Patent: WO2008/70014,2008,A2 .Location in patent: Page/Page column 58.

13
[ 3480-87-3 ]
[ 24835-08-3 ]
[ 1028119-76-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; at 0 - 20℃; for 5h;	2-Nitrobenzyl amine hydrochloride (2.27 g, 12.0 mmol), 3-hydroxy-3-phenyl propionic acid (2.00 g, 12.0 mmol), triethylamine (1.34 g, 13.3 mmol) were added to tetrahydrofuran (50 ml) and the reaction mixture was ice cooled. Under ice cooled condition, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.33 g, 12.0 mmol) was added thereto and stirred at room temperature for five hours. The reaction mixture was poured into dilute hydrochloric acid water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude crystal was washed with a mixture of hexane-ether (2:1) to obtain 3-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide (3.32 g). Yield: 92% Physical properties: Melting point 145.1C

References: [1]Patent: EP2085392,2009,A1 .Location in patent: Page/Page column 56.

14
[ 1203707-79-2 ]
[ 24835-08-3 ]
[ 1203707-80-5 ]

References: [1]Chemistry Letters,2009,vol. 38,p. 1042 - 1043.

15
[ 1243610-54-9 ]
[ 24835-08-3 ]
[ 1243610-47-0 ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3488 - 3499.

16
[ 24835-08-3 ]
[ 5231-87-8 ]
[ 1243610-51-6 ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3488 - 3499.

17
[ 1165931-74-7 ]
[ 24835-08-3 ]
[ 1254041-95-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃; for 5h;	Triethylamine (3.7 ml, 26 mmol) was added to a stirred mixture of 2-(4-chloro-2- fluoro-3-methoxyphenyl)-4,5-dichloro-6-methoxycarbonylpyrimidine (prepared as described in example 7) (4.0 g, 11 mmol) and <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (3.1 g, 16 mmol), in dichloromethane (40 ml). The reaction mixture was stirred at ambient temperature for 5 hours, then ethyl acetate added and the resulting solution washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue purified by column chromatography on silica using dichloromethane as eluent to provide 5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-6-methoxycarbonyl-4- (2-nitrophenylmethylamino)-pyrimidine as a yellow solid (4.45 g, 84%). Characterising data for this compound are as follows: Melting point: 123-125 0C;1H nmr (400 MHz, CDCI3) δH 8.10 (1 H, d), 7.73 (1 H, d), 7.68 (1 H, t), 7.61 (1 H, t), 7.48 (1H, t), 7.28 (1 H, d), 6.71 (1 H, br t), 5.10 (2H, d), 3.98 (3H, s) ppm

References: [1]Patent: WO2010/125332,2010,A1 .Location in patent: Page/Page column 33.

18
[ 24424-99-5 ]
[ 24835-08-3 ]
[ 163423-99-2 ]