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[ CAS No. 4487-57-4 ] {[proInfo.proName]}

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Chemical Structure| 4487-57-4
Chemical Structure| 4487-57-4
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Product Details of [ 4487-57-4 ]

CAS No. :4487-57-4 MDL No. :MFCD09832226
Formula : C5H2Br2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RZZGFCFQBVRQSX-UHFFFAOYSA-N
M.W : 281.89 Pubchem ID :16099850
Synonyms :

Calculated chemistry of [ 4487-57-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.46
TPSA : 58.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.103 mg/ml ; 0.000365 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.15 mg/ml ; 0.000531 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.221 mg/ml ; 0.000783 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.3

Safety of [ 4487-57-4 ]

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 [ 4487-57-4 ]

* 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 [ 4487-57-4 ]
  • Downstream synthetic route of [ 4487-57-4 ]

[ 4487-57-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 4487-57-4 ]
  • [ 50786-37-3 ]
Reference: [1] Patent: WO2010/78408, 2010, A1, . Location in patent: Page/Page column 136
  • 2
  • [ 607373-82-0 ]
  • [ 4487-57-4 ]
YieldReaction ConditionsOperation in experiment
75% With phosphorus(V) oxybromide In acetonitrile at 20℃; for 3 h; Heating / reflux Step 2.2, 4-Dibromo-5-nitropyridine Phosphorous oxybromide (5.73 g, 20 mmol) was added to a suspension of the product from Step 1 (1.70 g, 10 mmol) in acetonitrile (20 mL) at rt then heated to reflux for 3 h. The reaction mixture was cooled and carefully poured onto ice and sat. aq. K2C03 then extracted with EtOAc. The organic extracts were combined, washd with water and brine, dried (MgS04), filtered and concentrated to dive the title compound (2.1 g, 75 percent) as a dark solid.
75% With phosphorus(V) oxybromide In acetonitrile at 20℃; for 3 h; Heating / reflux Step 2.2, 4-Dibromo-5-nitropyridine Phosphorous oxybromide (5.73 g, 20 mmol) was added to a suspension of the product from Step 1 (1.70 g, 10 mmol) in acetonitrile (20 mL) at rt then heated to reflux for 3 h. The reaction mixture was cooled and carefully poured onto ice and sat. aq. K2C03 then extracted with EtOAc. The organic extracts were combined, washd with water and brine, dried (MgS04), filtered and concentrated to dive the title compound (2.1 g, 75 percent) as a dark solid.
66% With phosphorus(V) oxybromide In acetonitrile at 90℃; for 4 h; To a solution of 2-hydroxy-4-methoxy-5-nitropyridine (10 g, 59 mmole) in acetonitrile (60 mL) was added POBr3 (33.7 g, 117.6 mmole). The reaction mixture was heated to 9O0C for 4 h. The mixture was allowed to cool to RT and then poured onto saturated K2CO3ZiCe water. The product was extracted with EtOAc (2 x 250 mL), washed with brine and dried over Na2SO4. Concentration of the EtOAc solution under vacuum provided a light brown solid (10.9 g, 66percent) which was used without further purification: LC/MS: m/z 283 [M+H]+, single component.
Reference: [1] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 94
[2] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 94
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1508 - 1511
[4] Patent: WO2006/113837, 2006, A2, . Location in patent: Page/Page column 36; 63
[5] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 1, p. 42 - 46
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
  • 3
  • [ 850663-54-6 ]
  • [ 4487-57-4 ]
YieldReaction ConditionsOperation in experiment
41.1% With phosphorus(V) oxybromide In acetonitrile at 80℃; for 2 h; Inert atmosphere Into a 250 mL 3 -necked round-bottom flask purged and maintained with nitrogen was added a solution of 4-chloro-5-nitropyridin-2-ol (1 1.5 g, 65.9 mmol) in CH3CN (1 10 mL), followed by addition of POBr3 (23.1 g). The resulting solution was stirred at 80 °C for 2 hours. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was suspended in 500 mL of ice water. The resulting solids were collected by filtration and dried under vacuum to afford 2,4- dibromo-5-nitropyridine (7.66 g, 41.1percent) as a light yellow solid, which was carried forward without purification.
Reference: [1] Patent: WO2014/81718, 2014, A1, . Location in patent: Page/Page column 115
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 22, p. 8877 - 8895
[3] Patent: WO2013/117645, 2013, A1, . Location in patent: Paragraph 00543
[4] Patent: WO2018/119441, 2018, A1, . Location in patent: Paragraph 00677
  • 4
  • [ 31872-62-5 ]
  • [ 4487-57-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 2 - 5
[2] Patent: WO2009/62059, 2009, A2, . Location in patent: Page/Page column 32
[3] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 1, p. 42 - 46
[4] Patent: WO2006/113837, 2006, A2,
[5] Patent: WO2005/37197, 2005, A2,
  • 5
  • [ 13091-23-1 ]
  • [ 4487-57-4 ]
Reference: [1] Patent: WO2014/81718, 2014, A1,
  • 6
  • [ 4487-57-4 ]
  • [ 84487-15-0 ]
YieldReaction ConditionsOperation in experiment
95% With ammonia; triethylamine In tetrahydrofuran; methanol at 20℃; for 50 h; Step 1. 2-bromo-5-nitro-4-pyridinamine Under nitrogen, to a solution of 2, 4-dibromo-5-nitropyridine in THF (150 mL), was added ammonia (2. OM in MeOH), followed with triethylamine (5mL). This mixture was then stirred at rt for 50 h. The reaction mixture was concentrated, taken up in EtOAC, filtered through a silica gel pad, and then concentrated in vacuo to afford the title compound (3.67 g, 95percent).
95% With ammonia; triethylamine In tetrahydrofuran; methanol at 20℃; for 50 h; Step 1. 2-bromo-5-nitro-4-pyridinamine Under nitrogen, to a solution of 2, 4-dibromo-5-nitropyridine in THF (150 mL), was added ammonia (2. OM in MeOH), followed with triethylamine (5mL). This mixture was then stirred at rt for 50 h. The reaction mixture was concentrated, taken up in EtOAC, filtered through a silica gel pad, and then concentrated in vacuo to afford the title compound (3.67 g, 95percent).
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 1, p. 42 - 46
[2] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 102
[3] Patent: WO2005/37197, 2005, A2, . Location in patent: Page/Page column 102
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