[ CAS No. 562825-95-0 ] {[proInfo.proName]}

Name: 562825-95-0|N-Ethyl-3-nitropyridin-4-amine|97%
Brand: Ambeed
SKU: A673188
Price: 8.0 USD
Availability: InStock
Rating: 95 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 562825-95-0

Structure of 562825-95-0 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 562825-95-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 562825-95-0 ]

SDS Specification

Alternatived Products of [ 562825-95-0 ]

Product Details of [ 562825-95-0 ]

CAS No. :	562825-95-0	MDL No. :	MFCD02266948
Formula :	C₇H₉N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RFSOTSMANIOZPD-UHFFFAOYSA-N
M.W :	167.17	Pubchem ID :	21937597
Synonyms :

Calculated chemistry of [ 562825-95-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.17
TPSA :	70.74 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.23
Log Po/w (MLOGP) :	0.2
Log Po/w (SILICOS-IT) :	-0.82
Consensus Log Po/w :	0.72

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.04
Solubility :	1.51 mg/ml ; 0.00904 mol/l
Class :	Soluble
Log S (Ali) :	-2.68
Solubility :	0.352 mg/ml ; 0.00211 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	0.958 mg/ml ; 0.00573 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 562825-95-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 562825-95-0 ]

* 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.

Upstream synthesis route of [ 562825-95-0 ]
Downstream synthetic route of [ 562825-95-0 ]

[ 562825-95-0 ] Synthesis Path-Upstream 1~5

1
[ 31872-62-5 ]
[ 75-04-7 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	at 85℃; for 2 h;	A solution consisting of 4-methoxy-3-nitropyridine (15.0 g, 97.3 MMOL) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 MMOL) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all VOLATILES IN VACUO afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.
99%	at 85℃; for 2 h;	A solution consisting of 4-methoxy-3-nitropyridine (15.0 g, 97.3 mmol) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 mmol) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.

Reference： [1] Patent: WO2005/11700, 2005, A1, . Location in patent: Page/Page column 84
[2] Patent: WO2005/46678, 2005, A1, . Location in patent: Page/Page column 77
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
[4] Patent: WO2008/71937, 2008, A1, . Location in patent: Page/Page column 21

2
[ 75-04-7 ]
[ 1796-84-5 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	at 85℃; for 2 h;	A solution consisting of 4-ethoxy-3-nitropyridine (15.0 g, 97.3 MMOL) and EtNH2 (46.5 mL, 70percent aq. solution, 584 MMOL) in ETOH (30 mL) was stirred at 85 °C in a pressure vessel for 2 h. Removal of all VOLATILES IN VACUO afforded the title compound (16.2 g, 99 percent). MS (ES+) m/z 168 (M+H) +.
99%	at 85℃; for 2 h;	A solution consisting of 4-ethoxy-3-nitropyridine (15.0 g, 97.3 mmol) and EtNH2 (46.5 mL, 70percent aq. solution, 584 mmol) in EtOH (30 mL) was stirred at 85 °C in a pressure vessel for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 percent). MS (ES+) m/z 168 (M+H) +.

Reference： [1] Patent: WO2005/11700, 2005, A1, . Location in patent: Page/Page column 121
[2] Patent: WO2005/46678, 2005, A1, . Location in patent: Page/Page column 80

3
[ 75-04-7 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	for 2 h; Heating / reflux	Preparation of Ethyl-(3-nitropyridin-4-yl)amine 4-Methoxy-3-nitropyridine hydrochloride (11.2g, 58.9mmol) in ethanol (75ml) was treated with a 70percent solution of ethylamine in water (64ml) and heated under reflux for 2 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue dissolved in ethyl acetate and water. The mixture was extracted (x3) with ethyl acetate, washed with water and saturated aqueous sodium chloride solution before drying over magnesium sulfate. Evaporation of the solvent afforded the title compound (11.7g, 96percent).¹H NMR (400 MHz, DMSO-D6) δ ppm 1.18 (t, J=7.14 Hz,3H), 3.41 (m, 2H), 6.98 (d, J=6.32 Hz, 1 H), 8.24 (d, J=6.32 Hz, 1 H)₁ 8.39 (br, 1 H), 9.00 (s, 1 H). MS m/z 168 (M+1)⁺.
88%	for 3 h; Heating / reflux	4-Methoxy-3-nitropyridine hydrochloride (11. 2g, 58.9 mmol) in ethanol (75ml) was treated with a 70percent solution of ethylamin in water (32mi) and heated under reflux for 1 hour. Further ethylamin solution (32m1) was added and the mixture heated under reflux for a further 2 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue dissolved in ethyl acetate, washed (x3) with water and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo to afford the title compound (8.7g, 88percent) ; MS (ES+) m/e 168 [M+H] +.

Reference： [1] Patent: WO2006/63167, 2006, A1, . Location in patent: Page/Page column 70
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 14, p. 3402 - 3406
[3] Patent: WO2005/46678, 2005, A1, . Location in patent: Page/Page column 84

4
[ 1681-37-4 ]
[ 75-03-6 ]
[ 562825-95-0 ]

Reference： [1] Molecules, 2017, vol. 22, # 2,

5
[ 13091-23-1 ]
[ 562825-95-0 ]

Reference： [1] Patent: US2003/212111, 2003, A1,

[ 562825-95-0 ] Synthesis Path-Downstream 1~35

1
[ 562825-95-0 ]
1-ethyl-7-bromo-1H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1935,vol. 518,p. 274,287

2
[ 562825-95-0 ]
[ 146950-67-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen;palladium 10% on activated carbon; In ethanol; for 18h;	Preparation of N4-ethylpyridine-3,4-diamineHN.>. "2Ethyl-(3-nitropyridin-4-yl)amine (8.7g, 52.0mmol) in ethanol (150ml) was hydrogenated for 18 hours in the presence of 10% palladium on carbon. After filtration of the catalyst through celite, the filtrate was concentrated in vacuo to afford the title compound (6.7g, 94%). 1H NMR (400 MHz, DMSO-D6) delta ppm 1.19 (m, 3H), 3.09 (m, 2H), 4.53 (br, 2H),5.21 (br, 1 H), 6.31 (d, J=5.22 Hz, 1 H), 7.57 (d, J=5.36 Hz, 1 H), 7.62 (s, 1 H). MS (ES+) m/e 138 [M+H]+.
	With palladium 10% on activated carbon; hydrogen; In ethanol;	To a solution of 4-amino-3-nitropyridine (2.0 mmol) in DMF (10 mL), NaH (2.2 mmol) was addedslowly, the mixture was stirred at room temperature for 30 min. Then ethyl iodine (2.0 mmol) wasadded slowly into the mixture until the reaction is finished monitored by TLC. Then the solvent wasevaporated and the residue was purified by silica gel chromatography by DCM/MeOH system toafford 4-ethylamino-3-nitropydine.To a solution of 4-ethylamino-3-nitropydine (1.0 mmol) in EtOH (10 mL), 10% Pd/C was added.Then the mixture was reduced by catalytic hydrogenation. Until the completion of the reaction,the Pd/C was filtered and the solvent was evaporated. The product was used in the next step withoutfurther purification.The solution of substituted 4-ethylamino-3-aminopydine (0.5 mmol), benzaldehyde (0.5 mmol)with sodium pyrosulfite (0.5 mmol) was stirred in DMF (8 mL) under 120 C overnight. On completionof the reaction, the solvent was evaporated and the residue was purified by silica gel chromatographyby DCM/MeOH system to afford the final product. If necessary, the crude product could berecrystallized in DCM to afford pure compound [31].

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406
[2]Patent: WO2006/63167,2006,A1 .Location in patent: Page/Page column 70
[3]Justus Liebigs Annalen der Chemie,1935,vol. 518,p. 274,287
[4]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5
[5]Molecules,2017,vol. 22
[6]Patent: WO2008/71937,2008,A1 .Location in patent: Page/Page column 21

3
[ 75-04-7 ]
4-chloro-3-nitro-pyridine hydrochloride [ No CAS ]
[ 562825-95-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1935,vol. 518,p. 274,287

4
[ 562825-95-0 ]
[ 607371-01-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With bromine; sodium acetate; In acetic acid; at 100℃; for 18h;	A mixture consisting of ethyl (3-nitropyridin-4-yl) amine (11.76 g, 70 MMOL) in acetic acid (140 mL) with sodium acetate (28.7 g, 350 MMOL) and bromine (13.44 g, 84 MMOL) was stirred in a sealed flask at 100 C for 18 h. Most of the solvent was removed in vacuo and the residue partitioned between CH2CI2 and water and the aqueous layer basified with NAHCO3. The organic extract was washed with water then brine, dried (NA2SO4) and all volatiles removed in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate: hexane (2: 8) to afford the title compound (10.4 g, 60%). MS: (M+H) + = m/z 246.
60%	With bromine; sodium acetate; In acetic acid; at 100℃; for 18h;	A mixture of ethyl (3-nitropyridin-4-yl) amine (11.8 g, 70.0 MMOL), acetic acid (140 mL), sodium acetate (28.7 g, 0.35 mol) and bromine (13.4 g, 84.0 MMOL) was stirred in a pressure vessel at 100 C for 18 h. The solvent was removed in vacuo and the residue partitioned between CH2CI2 and water. The aqueous layer was made basic (PH-8) with NAHCO3 and further extracted with CH2CI2. The combined organic extracts were washed with water, brine and dried (NA2SO4). The solvent was removed in vacuo. and the residue subjected to flash chromatography (20% EtOAc/hexanes, silica gel) to give 10.4 g (60%) of the desired compound. MS (ES+) m/z 246 (M+H) +.
43 - 60%	With bromine; sodium acetate; In acetic acid; at 100℃; for 18 - 20h;	A mixture consisting of ethyl (3-nitropyridin-4-yl) amine (11.76 g, 70 mmol) in acetic acid (140 ml) with sodium acetate (28.7 g, 350 mmol) and bromine (13.44 g, 84 mmol) was stirred in a sealed flask at 100 oc for 18 h. Most of the solvent was removed in vacuo and the residue partitioned between CH2CI2 and water and the aqueous layer basified with NaHCO3. The organic extract was washed with water then brine, dried (Na2SO4) and all volatiles removed in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate: hexane (2: 8) to afford the title compound (10.4 g, 60%). MS: (M+H) + = m/z 246.; A mixture of ethyl (3-nitropyridin-4-yl) amine (11.8 g, 70.0 mmol), acetic acid (140 mL), sodium acetate (28.7 g, 0.35 mol) and bromine (13.4 g, 84.0 mmol) was stirred in a pressure vessel at 100 C for 18 h. The solvent was removed in vacuo and the residue partitioned between CH2CI2 and water. The aqueous layer was made basic (pH No. 8) with NaHCO3 and further extracted with CH2CI2. The combined organic extracts were washed with water, brine and dried (Na2SO4). The solvent was removed in vacuo. and the residue subjected to flash chromatography (20% EtOAc/hexanes, silica gel) to give 10.4 g (60%) of the desired compound. MS (ES+) m/z 246 (M+H) +.; To a solution of the product of 14 (a) (3. 0g, 17. 9mmol) in acetic acid (40ml) was added bromine (3.12g, 1ml, 19. 7mmol) and the mixture was heated at 100C for 20 hours. After cooling the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was washed with water (x3), dried and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 50% dichloromethane in ethyl acetate afforded the title compound (1.9g, 43%).'H NMR (DMSO-d6) 8.73 (1H, s), 8.52 (1H, s), 7.0 (1H, br), 3.25 (2H, m), 1.16 (3H, t, J 7.2Hz).

Reference： [1]Patent: WO2005/11700,2005,A1 .Location in patent: Page/Page column 85
[2]Patent: WO2005/11700,2005,A1 .Location in patent: Page/Page column 121-122
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3407 - 3411
[4]Patent: WO2005/46678,2005,A1 .Location in patent: Page/Page column 77; 80; 84-85

5
4-methoxy-3-nitropyridine hydrochloride [ No CAS ]
[ 75-04-7 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; water; for 2h;Heating / reflux;	Preparation of Ethyl-(3-nitropyridin-4-yl)amine 4-Methoxy-3-nitropyridine hydrochloride (11.2g, 58.9mmol) in ethanol (75ml) was treated with a 70% solution of ethylamine in water (64ml) and heated under reflux for 2 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue dissolved in ethyl acetate and water. The mixture was extracted (x3) with ethyl acetate, washed with water and saturated aqueous sodium chloride solution before drying over magnesium sulfate. Evaporation of the solvent afforded the title compound (11.7g, 96%).1H NMR (400 MHz, DMSO-D6) delta ppm 1.18 (t, J=7.14 Hz,3H), 3.41 (m, 2H), 6.98 (d, J=6.32 Hz, 1 H), 8.24 (d, J=6.32 Hz, 1 H)1 8.39 (br, 1 H), 9.00 (s, 1 H). MS m/z 168 (M+1)+.
88%	In ethanol; water; for 3h;Heating / reflux;	4-Methoxy-3-nitropyridine hydrochloride (11. 2g, 58.9 mmol) in ethanol (75ml) was treated with a 70% solution of ethylamin in water (32mi) and heated under reflux for 1 hour. Further ethylamin solution (32m1) was added and the mixture heated under reflux for a further 2 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue dissolved in ethyl acetate, washed (x3) with water and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo to afford the title compound (8.7g, 88%) ; MS (ES+) m/e 168 [M+H] +.

Reference： [1]Patent: WO2006/63167,2006,A1 .Location in patent: Page/Page column 70
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406
[3]Patent: WO2005/46678,2005,A1 .Location in patent: Page/Page column 84

6
[ 31872-62-5 ]
[ 75-04-7 ]
[ 562825-95-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	In ethanol; water; at 85℃; for 2h;	A solution consisting of 4-methoxy-3-nitropyridine (15.0 g, 97.3 MMOL) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 MMOL) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all VOLATILES IN VACUO afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.
99%	In ethanol; water; at 85℃; for 2h;	A solution consisting of 4-methoxy-3-nitropyridine (15.0 g, 97.3 mmol) with ethyl amine (46.5 mL of 70percent aqueous solution, 584 mmol) in ethanol (30 mL) was stirred at 85 °C in a sealed flask for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 percent). MS: (M+H) + = m/z 168.

Reference： [1]Patent: WO2005/11700,2005,A1 .Location in patent: Page/Page column 84
[2]Patent: WO2005/46678,2005,A1 .Location in patent: Page/Page column 77
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5
[4]Patent: WO2008/71937,2008,A1 .Location in patent: Page/Page column 21

7
[ 562825-95-0 ]
[ 607368-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406

8
[ 562825-95-0 ]
[ 607368-87-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2 - 5
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406

9
[ 562825-95-0 ]
[ 607371-03-9 ]