[ CAS No. 908248-27-1 ]

Name: 908248-27-1|2-Amino-5-nitropyridin-3-ol|95%
Brand: Ambeed
SKU: A139761
Price: 30.0 USD
Availability: InStock
Rating: 97 (40 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

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

2D 3D

Structure of 908248-27-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 908248-27-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 908248-27-1 ]

SDS Specification

Alternatived Products of [ 908248-27-1 ]

Product Details of [ 908248-27-1 ]

CAS No. :	908248-27-1	MDL No. :	MFCD13193356
Formula :	C₅H₅N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UXLVADZLQKGFIG-UHFFFAOYSA-N
M.W :	155.11 g/mol	Pubchem ID :	5373425
Synonyms :

Calculated chemistry of [ 908248-27-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	39.49
TPSA :	104.96 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) :	-7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.25
Log Po/w (XLOGP3) :	-0.02
Log Po/w (WLOGP) :	0.29
Log Po/w (MLOGP) :	-1.48
Log Po/w (SILICOS-IT) :	-1.89
Consensus Log Po/w :	-0.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.13
Solubility :	11.6 mg/ml ; 0.0747 mol/l
Class :	Very soluble
Log S (Ali) :	-1.73
Solubility :	2.86 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.46
Solubility :	54.2 mg/ml ; 0.349 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.16

Safety of [ 908248-27-1 ]

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

Application In Synthesis of [ 908248-27-1 ]

* 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.

Upstream synthesis route of [ 908248-27-1 ]
Downstream synthetic route of [ 908248-27-1 ]

[ 908248-27-1 ] Synthesis Path-Upstream 1~4

1
[ 21594-54-7 ]
[ 908248-27-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: With sodium hydroxide; water In ethanol at 80℃; for 3 h; Stage #2: With hydrogenchloride; sodium carbonate In ethanol; water	A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6- nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 °C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.
86%	Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 3 h; Stage #2: With hydrogenchloride In ethanol; water Stage #3: With sodium carbonate In ethanol; water	3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 ⁰C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pΗ adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.
86%	Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 3 h; Stage #2: With hydrogenchloride In ethanol; water Stage #3: With sodium carbonate In ethanol; water	3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 ⁰C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.

39%	With sodium hydroxide In ethanol; water at 80℃; for 3 h;	Into a 500-mL round-bottom flask, was placed a solution of 6-nitro-2H,3H-[1,3]oxazolo[4,5-b]pyridin-2-one (30 g, 165.65 mmol, 1.00 equiv) in ethanol (130 mL). Then a solution of sodium hydroxide (24 g, 600.00 mmol, 3.62 equiv) in water (225 mL) was added. The resulting solution was stirred for 3 h at 80° C. The reaction was then quenched by the addition of 48 mL of concentrated hydrochloric. The pH value of the solution was adjusted to 8 with 2M sodium carbonate. The solids were collected by filtration. This resulted in 10 g (39percent) of 2-amino-5-nitropyridin-3-ol (I-12) as a yellow solid.
37%	With water; sodium hydroxide In tetrahydrofuran at 85℃; for 2 h;	10percent Aqueous sodium hydroxide solution (44.40 mmol, 17.8 mL) was added to a suspension of 6-nitrooxazolo [ 4 , 5- b]pyridin-2 (3H) -one (11.10 mmol, 2 .00 g) in THF (10 mL) . The mixture was heated at 85°C for 2 hours. The mixture was cooled (ice/water bath) then acidified to pH6 (0774) (concentrated hydrochloric acid) . The resulting (0775) precipitate was isolated by filtration, washed with water then dried under suction to give the title compound as an orange powder (4.30 g, 37percent).

Reference： [1] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 120-121
[2] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 103; 104
[4] Patent: US2014/274926, 2014, A1, . Location in patent: Paragraph 0529; 0530
[5] Patent: WO2015/115673, 2015, A1, . Location in patent: Page/Page column 76-77

2
[ 896161-12-9 ]
[ 908248-27-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	at 150℃; for 3 h;	2-amino-3-hydroxy-5-nitropyridine Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol). The solid mixture was heated at 150° C. (upon which the solids fused; the evolution of a gas was also apparent). The mixture was held at 150° C. for three hours upon which reaction was deemed complete by LC-MS. After allowing to cool to 80° C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3100 ml). The combined organic extracts were washed with water (2100 mL), dried (Na₂SO₄), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10percent) gradient as eluent to give the product as a solid (0.138 g, 49 percent) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).
49%	at 150℃; for 3 h;	2-amino-3-hydroxy-5-nitropyridine; Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol). The solid mixture was heated at 150° C. upon which the solids fused (the evolution of a gas was also apparent). The mixture was held at 150° C. for three hours upon which reaction was deemed complete by LC-MS. After allowing to cool to 80° C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3.x.100 ml). The combined organic extracts were washed with water (2.x.100 mL), dried (Na₂SO₄), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10percent) gradient as eluent to give the product as a solid (0.138 g, 49percent) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).

Reference： [1] Patent: US2006/194801, 2006, A1, . Location in patent: Page/Page column 55
[2] Patent: US2006/205773, 2006, A1, . Location in patent: Page/Page column 32

3
[ 16867-03-1 ]
[ 908248-27-1 ]

Reference： [1] Patent: US2014/274926, 2014, A1,
[2] Patent: WO2015/115673, 2015, A1,

4
[ 60832-72-6 ]
[ 908248-27-1 ]

Reference： [1] Patent: US2014/274926, 2014, A1,
[2] Patent: WO2015/115673, 2015, A1,

[ 908248-27-1 ] Synthesis Path-Downstream 1~15

1
[ 896161-12-9 ]
[ 908248-27-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With pyridine hydrochloride; at 150℃; for 3.0h;	2-amino-3-hydroxy-5-nitropyridine Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol). The solid mixture was heated at 150 C. (upon which the solids fused; the evolution of a gas was also apparent). The mixture was held at 150 C. for three hours upon which reaction was deemed complete by LC-MS. After allowing to cool to 80 C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3100 ml). The combined organic extracts were washed with water (2100 mL), dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10%) gradient as eluent to give the product as a solid (0.138 g, 49 %) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).
49%	With pyridine hydrochloride; at 150℃; for 3.0h;	2-amino-3-hydroxy-5-nitropyridine; Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol). The solid mixture was heated at 150 C. upon which the solids fused (the evolution of a gas was also apparent). The mixture was held at 150 C. for three hours upon which reaction was deemed complete by LC-MS. After allowing to cool to 80 C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (2×100 mL), dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10%) gradient as eluent to give the product as a solid (0.138 g, 49%) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).

Reference： [1]Patent: US2006/194801,2006,A1 .Location in patent: Page/Page column 55
[2]Patent: US2006/205773,2006,A1 .Location in patent: Page/Page column 32

2
[ 21594-54-7 ]
[ 908248-27-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6- nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86% yield as a yellow solid.
86%		3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 0C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pEta adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86% yield as a yellow solid.
86%		3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 0C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86% yield as a yellow solid.

39%	With sodium hydroxide; In ethanol; water; at 80℃; for 3.0h;	Into a 500-mL round-bottom flask, was placed a solution of 6-nitro-2H,3H-[1,3]oxazolo[4,5-b]pyridin-2-one (30 g, 165.65 mmol, 1.00 equiv) in ethanol (130 mL). Then a solution of sodium hydroxide (24 g, 600.00 mmol, 3.62 equiv) in water (225 mL) was added. The resulting solution was stirred for 3 h at 80 C. The reaction was then quenched by the addition of 48 mL of concentrated hydrochloric. The pH value of the solution was adjusted to 8 with 2M sodium carbonate. The solids were collected by filtration. This resulted in 10 g (39%) of 2-amino-5-nitropyridin-3-ol (I-12) as a yellow solid.
37%	With water; sodium hydroxide; In tetrahydrofuran; at 85℃; for 2.0h;	10% Aqueous sodium hydroxide solution (44.40 mmol, 17.8 mL) was added to a suspension of 6-nitrooxazolo [ 4 , 5- b]pyridin-2 (3H) -one (11.10 mmol, 2 .00 g) in THF (10 mL) . The mixture was heated at 85C for 2 hours. The mixture was cooled (ice/water bath) then acidified to pH6 (0774) (concentrated hydrochloric acid) . The resulting (0775) precipitate was isolated by filtration, washed with water then dried under suction to give the title compound as an orange powder (4.30 g, 37%).

Reference： [1]Patent: WO2009/23844,2009,A2 .Location in patent: Page/Page column 120-121
[2]Patent: WO2010/21797,2010,A1 .Location in patent: Page/Page column 85
[3]Patent: WO2010/24980,2010,A1 .Location in patent: Page/Page column 103; 104
[4]Patent: US2014/274926,2014,A1 .Location in patent: Paragraph 0529; 0530
[5]Patent: WO2015/115673,2015,A1 .Location in patent: Page/Page column 76-77

3
[ 908248-27-1 ]
[ 3132-64-7 ]
[ 908248-28-2 ]

Yield	Reaction Conditions	Operation in experiment
46%		(7-nitro-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol; Into a 75 mL sealed tube were combined <strong>[908248-27-1]2-amino-3-hydroxy-5-nitropyridine</strong> (0.138 g, 0.000890 mol), N,N-dimethylformamide (4.1 mL) and potassium carbonate (0.39 g, 0.0028 mol). The mixture was allowed to stir at room temperature for 10 minutes then 1-bromo-2,3-epoxypropane (0.12 g, 0.00089 mol) was added in one portion. The flask was sealed, then heated to 110 C. and stirred overnight. After allowing to cool, the mixture was concentrated under vacuum to give a crude solid which was dissolved in EtOAc (75 mL), washed with water and brine, then dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using MeOH/CH2Cl2 (0-10% gradient) as eluent to give a solid (0.092 g, 46%). LC-MS 1.92 min. M/Z=212.0 (M+1). 1H NMR (d6-DMSO) 8.8 (d, 1 H), 7.8 (d, 1 H), 5.1 (t, 1H),4.2 (m, 1 H), 4.0 (m, 1H), 3.62 (m, 1H), 3.45 (m, 1H), 3.21 (m, 1H).

Reference： [1]Patent: US2006/205773,2006,A1 .Location in patent: Page/Page column 32

4
[ 908248-27-1 ]
[ 89-54-3 ]
4-chloro-3-[6-nitro-[1,3]oxazolo[4,5-b]pyridin-2-yl]aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With polyphosphoric acid; In water; Petroleum ether; at 150℃; for 48h;	Into a 1000-mL round-bottom flask, was placed 2-amino-5-nitropyridin-3-ol (9.5 g, 61.25 mmol, 1.00 equiv), <strong>[89-54-3]5-amino-2-chlorobenzoic acid</strong> (10.5 g, 61.20 mmol, 1.00 equiv), PPA (300 mL). The resulting solution was stirred for 2 days at 150° C. The reaction was then quenched by the addition of 1000 mL of water/ice. The pH value of the solution was adjusted to 7 with sodium hydroxide (aq.). The solids were collected by filtration. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 2 g (11percent) of 4-chloro-3-[6-nitro-[1,3]oxazolo[4,5-b]pyridin-2-yl]aniline (I-13) as a red solid.

Reference： [1]Patent: US2014/274926,2014,A1 .Location in patent: Paragraph 0531; 0532

5
[ 16867-03-1 ]
[ 908248-27-1 ]

Reference： [1]Patent: US2014/274926,2014,A1
[2]Patent: WO2015/115673,2015,A1

6
[ 60832-72-6 ]
[ 908248-27-1 ]

Reference： [1]Patent: US2014/274926,2014,A1
[2]Patent: WO2015/115673,2015,A1

7
[ 908248-27-1 ]
N-(3-(6-aminooxazolo[4,5-b]pyridin-2-yl)-4-chlorophenyl)pyrrolidine-1-carboxamide [ No CAS ]