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[ CAS No. 175422-04-5 ] {[proInfo.proName]}

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Chemical Structure| 175422-04-5
Chemical Structure| 175422-04-5
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Product Details of [ 175422-04-5 ]

CAS No. :175422-04-5 MDL No. :MFCD07369947
Formula : C5H2Br2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XIPATZUHJFQGQC-UHFFFAOYSA-N
M.W : 281.89 Pubchem ID :16038748
Synonyms :

Calculated chemistry of [ 175422-04-5 ]

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 : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 0.82
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0638 mg/ml ; 0.000226 mol/l
Class : Soluble
Log S (Ali) : -3.62
Solubility : 0.0681 mg/ml ; 0.000242 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 : 2.29

Safety of [ 175422-04-5 ]

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 [ 175422-04-5 ]

* 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 [ 175422-04-5 ]
  • Downstream synthetic route of [ 175422-04-5 ]

[ 175422-04-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 175422-04-5 ]
  • [ 39771-34-1 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 90℃; for 0.5 h; Heating / reflux
Stage #2: With sodium hydroxide In water
To a solution of 2,6-dibromo-4-nitro-pyridine (1.0 g, 3.54 mmol) in glacial acetic acid (20 ml.) was added Fe-powder (1.0 g, 17.74 mmol) at room temperature. The reaction mixture was refluxed for 900C for 30 min. After completion of reaction (TLC monitoring), water was added (100 mL), basified with 2N NaOH (pH 12-14). The resulting mixture was filtered through celite-bed and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with water, dried (Na2SO4), filtered and evaporated to dryness to get the desired product as an off white solid (0.80 g, 90percent). 1H NMR (DMSO-d6, 400 MHz): δ 6.67 (s, 2H) and 6.71 (br s, 2H).
70% With ammonia In tetrahydrofuran; water at 95℃; for 2.5 h; P. 2, 6-Dibromo-pyridin-4-ylamine A solution of 15.3 G (54.3 MMOL) 2,6-dibromo-4-nitro-pyridine and 18.5 ml (271.5 MMOL) 25percent aq. ammonia in 40 mi tetrahydrofurane was transferred to an autoclave and heated at 95 C for 2.5 h. After cooling to room temperature, the reaction was poured into water (200 mi) and extracted with dichloromethane (3 x 200 ML). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was crystallized from ethyl acetate/petroleum ether to afford 9.6 G (70percent) of the title compound as a yellow solid. m. p. 184-186 C.
Reference: [1] Patent: WO2009/74810, 2009, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2005/26164, 2005, A1, . Location in patent: Page/Page column 43
  • 2
  • [ 124-41-4 ]
  • [ 175422-04-5 ]
  • [ 117873-72-0 ]
YieldReaction ConditionsOperation in experiment
70% With methanol In tetrahydrofuran at 20℃; for 2 h; To a solution of compound S1 (2 g, 7.11 mmol) in THF (15 mL) was added MeONa/MeOH solution (1.2 mL, 6.05 mmol, 1.3 M). The reaction was stirred at room temperature for 2 hrs and quenched with water. The resulting mixture was extracted with EtOAc twice. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel column eluted with (PE/Acetone=30/1) to give the title compound (1.45 g, 70percent yield) as a white solid.
Reference: [1] Helvetica Chimica Acta, 1997, vol. 80, # 1, p. 86 - 96
[2] Patent: WO2017/35353, 2017, A1, . Location in patent: Paragraph 0905
  • 3
  • [ 67-56-1 ]
  • [ 175422-04-5 ]
  • [ 117873-72-0 ]
Reference: [1] Patent: US6339045, 2002, B1, . Location in patent: Example 1
[2] Patent: WO2009/24905, 2009, A1, . Location in patent: Page/Page column 83-84
[3] Patent: US2011/212998, 2011, A1, . Location in patent: Page/Page column 30
  • 4
  • [ 175422-04-5 ]
  • [ 117873-72-0 ]
Reference: [1] Patent: US6005112, 1999, A,
[2] Patent: US5691277, 1997, A,
  • 5
  • [ 98027-81-7 ]
  • [ 175422-04-5 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With trichlorophosphate In chloroform at 5 - 75℃; for 96 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In chloroform; water
C. 2,6-Dibromo-4-nitro-pyridine To a suspension of 22.7 G (76.2 MMOL) 2,6-dibromo-4-nitro-pyridin N-oxide in chloroform (120 ml) was added dropwise phosphorus trichloride (20 ML, 229 MMOL) at 5 C. The reaction mixture was heated to 75 C and refluxed for 4d. After the reaction was completed, the mixture was cautiously poured into 600 ml ice-water and the solution neutralized with sodium bicarbonate. The layers were separated and the water-layer was extracted with chloroform (3 x 150 ML). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate = 4 : 1) to give 15.5 G (72percent) of the title compound as a white solid. m. p. 122-123 C.
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1273 - 1276
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8307 - 8318
[3] Tetrahedron Letters, 2007, vol. 48, # 1, p. 113 - 117
[4] Patent: WO2005/26164, 2005, A1, . Location in patent: Page/Page column 41
[5] Helvetica Chimica Acta, 1997, vol. 80, # 1, p. 86 - 96
[6] European Journal of Inorganic Chemistry, 1998, # 9, p. 1205 - 1207
  • 6
  • [ 626-05-1 ]
  • [ 175422-04-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1273 - 1276
[2] European Journal of Inorganic Chemistry, 1998, # 9, p. 1205 - 1207
[3] Helvetica Chimica Acta, 1997, vol. 80, # 1, p. 86 - 96
[4] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3537 - 3540
[5] Patent: US2012/97899, 2012, A1,
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8307 - 8318
  • 7
  • [ 25373-69-7 ]
  • [ 175422-04-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1273 - 1276
[2] Helvetica Chimica Acta, 1997, vol. 80, # 1, p. 86 - 96
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8307 - 8318
  • 8
  • [ 175422-04-5 ]
  • [ 220616-68-2 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 36, p. 8464 - 8475
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