Home Cart 0 Sign in  
X

[ CAS No. 28489-45-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 28489-45-4
Chemical Structure| 28489-45-4
Chemical Structure| 28489-45-4
Structure of 28489-45-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 28489-45-4 ]

Related Doc. of [ 28489-45-4 ]

Alternatived Products of [ 28489-45-4 ]
Product Citations

Product Details of [ 28489-45-4 ]

CAS No. :28489-45-4 MDL No. :MFCD00092010
Formula : C6H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AJDDHNXZBGZBJN-UHFFFAOYSA-N
M.W : 154.12 Pubchem ID :543053
Synonyms :

Calculated chemistry of [ 28489-45-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.05
TPSA : 78.94 Ų

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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : -0.56
Log Po/w (SILICOS-IT) : -0.81
Consensus Log Po/w : 0.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 2.44 mg/ml ; 0.0158 mol/l
Class : Very soluble
Log S (Ali) : -2.31
Solubility : 0.757 mg/ml ; 0.00491 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.2
Solubility : 9.66 mg/ml ; 0.0627 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 28489-45-4 ]

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

Application In Synthesis of [ 28489-45-4 ]

* 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 [ 28489-45-4 ]
  • Downstream synthetic route of [ 28489-45-4 ]

[ 28489-45-4 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 33986-37-7 ]
  • [ 22280-60-0 ]
  • [ 56057-19-3 ]
  • [ 28489-45-4 ]
Reference: [1] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
  • 2
  • [ 28489-45-4 ]
  • [ 3430-10-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 3
  • [ 28489-45-4 ]
  • [ 22280-60-0 ]
YieldReaction ConditionsOperation in experiment
78% at 150℃; for 2 h; Example 1153-((5-Amino-6-methylpyridin-2-yl)ethynyl)-7,7-dimethyl-7,8-dihydroquinoone[00319] A mixture of 6-methyl-5-nitropyridin-2-ol (500 mg, 3.24 mmol), POCI3 (0.5 mL) and PCI5 (200 mg) is stirred at 150 °C for 2 h, cooled to r.t, poured onto ice, and extracted with DCM (3x20 mL). The combined organic phases are washed with water to reach pH 7, dried over Na2S04 and concentrated at reduced pressure. The obtained residue is dried at reduced pressure to give 6-chloro-2-methyl-3-nitropyridine (430 mg, 78percent) as light brown solid.[00320]According to General Procedure 2, 3-ethynyl-7,7-dimethyl-7,8-dihydroquinolin- 5(6/-/)-one (199 mg, 1 .00 mmol) is reacted with 6-chloro-2-methyl-3-nitropyridine (172 mg, 1.00 mmol) in the presence of PdCI2(PPh3)2 (42 mg, 0.06 mmol), P(f-Bu)3 (16 mg, 0.08 mmol), and TEA (1 .5 mL) in DMF (3 mL) at 100 °C for 3 h. The crude product is purified by column chromatography (silica gel) to give the intermediate product 7,7- dimethyl-3-((6-methyl-5-nitropyridin-2-yl)ethynyl)-7,8-dihydroquinolin-5(6/-/)-one (80 mg, 16percent) as yellow solid.[00321 ]7,7-dimethyl-3-((6-methyl-5-nitropyridin-2-yl)ethynyl)-7,8-dihydroquinolin-5(6/-/)- one (194 mg, 0.58 mmol) is dissolved in EtOAc (10 mL) and cooled down to 0 °C. A solution of SnCl2*2H2O (650 mg, 2.90 mmol) in concentrated aqueous HCI solution (1 mL) is added dropwise. The reaction mixture is stirred at r.t. for 3 h, poured onto ice, treated with 15percent aqueous NaOH solution to reach pH 9-10, and extracted with EtOAc (3x25 mL). The combined organic phases are dried over Na2SO4 and concentrated at reduced pressure. The obtained residue is purified by preparative TLC (silica gel, DCM/EtOH, 40: 1 ) to provide the title compound (34 mg, 19percent).1H NMR (De-DMSO), δΗ, 1 .05 (s, 6H), 2.29 (s, 3H), 2.59 (s, 2H), 3.03 (s, 2H), 5.51 (br s, 2H), 6.92 (d, 1 H), 7.24 (d, 1 H), 8.15 (s, 1 H), 8.83 (s, 1 H).LC/MS (M+H)+ = 306
63.8% at 100℃; for 2 h; The raw material 3 (150 mg) and PCl5(210 mg) and POCl3(180 mg) was placed in a round bottom flask and refluxed at 100 ° C for 2 h. The POCl was distilled off under reduced pressure3After stirring with water, the solid was precipitated and filtered under reduced pressure to give the crude product. Column chromatography gave pure product 4 (100 mg) in 63.8percent yield.
62% With phosphorus pentachloride; trichlorophosphate In DMF (N,N-dimethyl-formamide) at 110 - 115℃; for 8 h; (c) To 6-Hydroxy-3-nitro-2-picoline (15.73 g, 0.102 mol) was added PCls (5.73 g, 0.027 mol) and POCh (2.9 ml, 0.032 mol). This mixture was heated at 110-115°C for 3 hrs. However, the amount of POCh added was only enough to moisten the starting material. More POC13 (3 ml) was added, the reaction mixture heated at 110-115°C but only sublination of PCls (100°C) was observed. DMF (5 ml) was added and the solution was heated at 115°C for 5 hrs, cooled and poured into a slush of ice and water. A beige product precipitated and the water suspension was stirred for 48 hrs. The brown precipitate was filtered off and washed with water. Purification by dry-flash dichloromethane yielded 10.93 g (62 percent) of 6-chloro-2-picoline.
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[2] Patent: WO2012/52451, 2012, A1, . Location in patent: Page/Page column 113
[3] Patent: CN105906621, 2016, A, . Location in patent: Paragraph 0021
[4] Patent: WO2005/42464, 2005, A1, . Location in patent: Page/Page column 33
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
[6] Yakugaku Zasshi, 1952, vol. 72, p. 434[7] Chem.Abstr., 1953, p. 6404
[8] Patent: US5874427, 1999, A,
[9] Patent: EP875513, 1998, A1,
[10] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 74
  • 4
  • [ 28489-45-4 ]
  • [ 22280-60-0 ]
Reference: [1] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 29
  • 5
  • [ 10026-13-8 ]
  • [ 28489-45-4 ]
  • [ 22280-60-0 ]
Reference: [1] Patent: US6358972, 2002, B1,
  • 6
  • [ 22280-62-2 ]
  • [ 22280-60-0 ]
  • [ 28489-45-4 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
  • 7
  • [ 33986-37-7 ]
  • [ 22280-60-0 ]
  • [ 56057-19-3 ]
  • [ 28489-45-4 ]
Reference: [1] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
  • 8
  • [ 28489-45-4 ]
  • [ 22282-96-8 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6053
  • 9
  • [ 28489-45-4 ]
  • [ 22282-96-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 5, p. 795 - 798
  • 10
  • [ 22280-62-2 ]
  • [ 28489-45-4 ]
YieldReaction ConditionsOperation in experiment
78% at 0 - 10℃; for 1 h; (b) 6-Amino-3-nitro-2-picoline (20 g, 0.131 mol) was suspended in a mixture of conc. H2S04 (23.7 ml) and water (335 ml). More cone. H2S04 (20 ml) was added under ice- cooling, but the amine did not dissolve completely. The suspension was added in ice (100 g) before a solution of NaNO2 (13.53 g, 0.196 mol) in water (40 ml) was added drop wise. Gas evolution was observed. The brown suspension was stirred at 10°C for 1 hr, filtered and washed with water. The brown product was dried (freeze dryer) to achieve 15.78 g (78 percent) of 6-hydroxy-3-nitro-2-picoline.
56.3% With sulfuric acid; sodium nitrite In water at -5 - 20℃; for 2 h; The raw material 2 (5g) was added to 15mL water, the external temperature -5 dropping concentrated sulfuric acid 25mL, keep the internal temperature 0 ~ -5 under the conditions of slowly dropping NaNO2(2.48 g / 8 mL), and the mixture was stirred at 20 ° C for 2 hours. The reaction solution was poured into ice water and precipitated as a solid. The product 3 (4.7 g) was obtained by filtration under reduced pressure in a yield of 56.3percent.
80% With sulfuric acid; sodium nitrite In water 6-hydroxy-3-nitro-2-picoline
A suspension of 3.0 gm (19.6 mMol) 6-amino-3-nitro-2-picoline in 50 mL water containing 3.5 mL concentrated sulfuric acid was heated to effect solution.
The resultant solution was cooled to 0° C. and a solution of 2.0 gm (29.4 mMol) sodium nitrite in 10 mL water was added with vigorous stirring at a rate to maintain the reaction mixture <=10° C.
After 4 hours the reaction mixture was filtered.
The solid was washed with water and dried under reduced pressure to provide 2.4 gm (80percent) of the desired compound as a pale yellow solid.
MS(m/e): 153 (M+)
80% With sulfuric acid; sodium nitrite In water 6-hydroxy-3-nitro-2-picoline
A suspension of 3.0 gm (19.6 mMol) 6-amino-3-nitro-2-picoline in 50 mL water containing 3.5 mL concentrated sulfuric acid was heated to effect solution.
The resultant solution was cooled to 0°C and a solution of 2.0 gm (29.4 mMol) sodium nitrite in 10 mL water was added with vigorous stirring at a rate to maintain the reaction mixture <=10°C.
After 4 hours the reaction mixture was filtered.
The solid was washed with water and dried under reduced pressure to provide 2.4 gm (80percent) of the desired compound as a pale yellow solid.
MS(m/e): 153 (M+)

Reference: [1] Patent: WO2005/42464, 2005, A1, . Location in patent: Page/Page column 33
[2] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[3] Patent: CN105906621, 2016, A, . Location in patent: Paragraph 0020
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
[5] Yakugaku Zasshi, 1952, vol. 72, p. 434[6] Chem.Abstr., 1953, p. 6404
[7] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[8] Patent: US5874427, 1999, A,
[9] Patent: EP875513, 1998, A1,
[10] Patent: EP1857444, 2007, A1, . Location in patent: Page/Page column 21
[11] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 74
  • 11
  • [ 5467-69-6 ]
  • [ 28489-45-4 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With hydrogen bromide In acetic acid at 60℃; for 2 h;
Stage #2: With ammonia In diethyl ether; water
The product derived from step 1 (0.796g, 4.7mmol) was added to a of solution HBr (33percent) in acetic acid (5ml), the mixture was stirred at 60°C for 2h and concentrated under reduced pressure.
The residue was dissolved in diethyl ether (5ml), washed with 5percent aqueous ammonia (3ml) and water (3ml) and the organic phase was evaporated to give 0.63g (87percent) of 6-methyl-5-nitro-pyridin-2-ol as colourless powder.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1890 - 1894
[2] Patent: EP1894924, 2008, A1, . Location in patent: Page/Page column 23
  • 12
  • [ 22280-62-2 ]
  • [ 39745-39-6 ]
  • [ 21901-29-1 ]
  • [ 28489-45-4 ]
Reference: [1] Patent: US6011029, 2000, A,
  • 13
  • [ 1824-81-3 ]
  • [ 28489-45-4 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[3] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[4] Patent: CN105906621, 2016, A,
[5] Patent: WO2005/42464, 2005, A1,
  • 14
  • [ 109-06-8 ]
  • [ 28489-45-4 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
  • 15
  • [ 64-18-6 ]
  • [ 22280-60-0 ]
  • [ 28489-45-4 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 596,598
  • 16
  • [ 22280-62-2 ]
  • [ 22280-60-0 ]
  • [ 28489-45-4 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
  • 17
  • [ 28489-45-4 ]
  • [ 5467-69-6 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
[2] Patent: WO2009/155156, 2009, A1,
  • 18
  • [ 28489-45-4 ]
  • [ 5467-69-6 ]
Reference: [1] Patent: US6358972, 2002, B1,
  • 19
  • [ 28489-45-4 ]
  • [ 856834-95-2 ]
Reference: [1] Patent: US2018/170909, 2018, A1,
  • 20
  • [ 28489-45-4 ]
  • [ 17288-40-3 ]
Reference: [1] Patent: US6358972, 2002, B1,
  • 21
  • [ 28489-45-4 ]
  • [ 31224-43-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 22
  • [ 28489-45-4 ]
  • [ 17322-91-7 ]
Reference: [1] Patent: CN108164528, 2018, A,
[2] Patent: CN108218865, 2018, A,
[3] Patent: CN108383838, 2018, A,
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 28489-45-4 ]

Alcohols

Chemical Structure| 6854-07-5

[ 6854-07-5 ]

5-Nitro-2-oxo-3-pyridinecarboxylic Acid

Similarity: 0.72

Chemical Structure| 89640-67-5

[ 89640-67-5 ]

6-Hydroxypicolinamide

Similarity: 0.65

Chemical Structure| 149082-03-1

[ 149082-03-1 ]

(3,5-Dimethyl-4-nitropyridin-2-yl)methanol

Similarity: 0.62

Chemical Structure| 86454-13-9

[ 86454-13-9 ]

2-Hydroxy-6-methylisonicotinic acid

Similarity: 0.61

Chemical Structure| 188554-13-4

[ 188554-13-4 ]

2-Hydroxyisonicotinaldehyde

Similarity: 0.61

Nitroes

Chemical Structure| 5467-69-6

[ 5467-69-6 ]

6-Methoxy-2-methyl-3-nitropyridine

Similarity: 0.93

Chemical Structure| 18699-87-1

[ 18699-87-1 ]

2-Methyl-3-nitropyridine

Similarity: 0.84

Chemical Structure| 15513-52-7

[ 15513-52-7 ]

2,6-Dimethyl-3-nitropyridine

Similarity: 0.81

Chemical Structure| 6635-90-1

[ 6635-90-1 ]

2-Methoxy-4-methyl-5-nitropyridine

Similarity: 0.80

Chemical Structure| 22280-62-2

[ 22280-62-2 ]

6-Amino-3-nitro-2-picoline

Similarity: 0.78

Related Parent Nucleus of
[ 28489-45-4 ]

Pyridines

Chemical Structure| 5467-69-6

[ 5467-69-6 ]

6-Methoxy-2-methyl-3-nitropyridine

Similarity: 0.93

Chemical Structure| 18699-87-1

[ 18699-87-1 ]

2-Methyl-3-nitropyridine

Similarity: 0.84

Chemical Structure| 15513-52-7

[ 15513-52-7 ]

2,6-Dimethyl-3-nitropyridine

Similarity: 0.81

Chemical Structure| 6635-90-1

[ 6635-90-1 ]

2-Methoxy-4-methyl-5-nitropyridine

Similarity: 0.80

Chemical Structure| 22280-62-2

[ 22280-62-2 ]

6-Amino-3-nitro-2-picoline

Similarity: 0.78