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[ CAS No. 959992-62-2 ] {[proInfo.proName]}

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Chemical Structure| 959992-62-2
Chemical Structure| 959992-62-2
Structure of 959992-62-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 959992-62-2 ]

CAS No. :959992-62-2 MDL No. :MFCD09834129
Formula : C7H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :OTGDCHNSXQUISE-UHFFFAOYSA-N
M.W : 215.05 Pubchem ID :20824376
Synonyms :

Calculated chemistry of [ 959992-62-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.56
TPSA : 34.15 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.342 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 1.12 mg/ml ; 0.00523 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.128 mg/ml ; 0.000593 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 959992-62-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 959992-62-2 ]

* 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 [ 959992-62-2 ]
  • Downstream synthetic route of [ 959992-62-2 ]

[ 959992-62-2 ] Synthesis Path-Upstream   1~8

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  • [ 20348-23-6 ]
Reference: [1] Patent: US2015/119385, 2015, A1,
  • 2
  • [ 959992-62-2 ]
  • [ 20348-23-6 ]
Reference: [1] Patent: WO2015/59668, 2015, A1,
  • 3
  • [ 337463-88-4 ]
  • [ 959992-62-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With borane-THF In tetrahydrofuran at 90℃; for 1.5 h;
Stage #2: With methanol In tetrahydrofuran at 90℃; for 0.333333 h;
Step 4 To a solution of Compound (9) (3.12 g, 13.7 mmol) in tetrahydrofuran (50 mL), borane-tetrahydrofuran complex (33 mL, 33.0 mmol) was added at room temperature. The solution was then stirred at 90°C for 1.5 hours. Methanol (2.0 mL) was added to the reaction solution, and then the mixture was stirred at 90°C for 20 minutes. The reaction solution was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried with anhydrous magnesium sulfate, and then concentrated in vacuo to yield subject compound (10) (3.17 g, 100percent) as a yellow powder.1H-NMR (DMSO-d6) 57.04 (1H, br s), 6.69 (1H, d, J = 7.8 Hz), 6.40 (1H, d, J = 7.8 Hz), 3.91 (2H, t, J = 4.2Hz), 3.19-3.23 (2H, m) LC/MS (Method A): 1.44 min, [M+H]+ = 215.2.
99% With diborane In tetrahydrofuran for 1 h; Cooling with ice; Reflux Under ice bath conditions, Borane in tetrahydrofuran (5.5 mL, 5.5 mmol, 1.0 M) Add dropwise to compound 3.2 (500 mg, 2.19 mmol) In a solution of tetrahydrofuran (25 mL), The reaction system was stirred under reflux with heating for 1 hour. The reaction was then carefully quenched with methanol (10 drops) under reflux. The mixture was cooled to room temperature and concentrated under reduced pressure to remove solvent. The residue was chromatographed on silica gel ( petroleum ether / ethyl acetate = 5/1) Purification afforded compound 23.1 (470 mg, yield: 99percent) It is a white solid.
87% With dimethylsulfide borane complex; potassium carbonate In tetrahydrofuran at 70℃; for 0.25 h; Inert atmosphere Part IV- Synthesis of 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]oxazine; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (1.35 g, 5.89 mmol) was dissolved inTHF (40 mL). Boranedimethylsulphide complex (2.0 Min THF, 5.89 mL, 11.79 mmol) wasadded and the resulting mixture heated to 70 °C under nitrogen for 15 minutes. Next, thereaction mixture was cooled to room temperature, quenched with methanol ( ~5 mL ), and then dried under vacuum to obtain a white solid. The crude material was dissolved indichloromethane and washed with H20. The aqueous phase was discarded and the organicphase was dried under vacuum to give 6-bromo-3,4-dihydro-2H-pyrido[3,2-b ][1,4]oxazine.Yield: 1.1 g (87percent). LCMS (ESI): calc. C7H7BrN20 = 214, 216; obs. M+H = 215, 217.
Reference: [1] Patent: EP2341052, 2011, A1, . Location in patent: Page/Page column 35; 36
[2] Patent: CN108623615, 2018, A, . Location in patent: Paragraph 0388; 0389; 0390
[3] Patent: WO2013/169864, 2013, A2, . Location in patent: Paragraph 00205
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YieldReaction ConditionsOperation in experiment
55%
Stage #1: at 90℃; for 5 h;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 70 - 90℃;
To a solution of 6-bromo-3-(2-bromoethoxy)-2-nitropyridine (4.5 g, 13.8 mmol) in glacial acetic acid (23 ml) was added iron (powder, 3.08 g, 55.2 mmol) in one portion. The reaction mixture was heated to 90°C during 5 hours, then cooled down, diluted in ethyl acetate and filtered through a silica gel plug using ethyl acetate as eluent. After evaporation, the residue was dissolved in DMF (50 ml). Potassium carbonate (5.72 g, 41.4 mmol) was added and the mixture was heated to 90°C for 2 hours, then to 70°C overnight. After evaporation of solvent, the residue was dissolved in DCM, salts were removed by filtration, and the crude compound was purified by silica gel flash chromatography (30 to 50percent ethyl acetate in petroleum ether) to give 6-bromo-3,4-dihydro-2H-pyrido[3,2- b][l,4]oxazine as a pale yellow oil (1.64 g, 55percent); Mass Spectrum [M+H]+ = 215; 1H NMR Spectrum (CDC13) 3.54-3.60 (m, 2H), 4.19 (t, 2H), 5.35 (bs, IH), 6.66 (d, IH), 6.82 (d, IH).
Reference: [1] Patent: WO2007/141473, 2007, A1, . Location in patent: Page/Page column 268; 269
[2] Patent: WO2011/59839, 2011, A1,
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Reference: [1] Patent: WO2011/59839, 2011, A1, . Location in patent: Page/Page column 65
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  • [ 443956-08-9 ]
  • [ 959992-62-2 ]
Reference: [1] Patent: WO2011/59839, 2011, A1,
[2] Patent: EP2341052, 2011, A1,
[3] Patent: WO2013/169864, 2013, A2,
[4] Patent: WO2007/141473, 2007, A1,
[5] Patent: CN108623615, 2018, A,
  • 7
  • [ 15128-82-2 ]
  • [ 959992-62-2 ]
Reference: [1] Patent: WO2011/59839, 2011, A1,
[2] Patent: EP2341052, 2011, A1,
  • 8
  • [ 443956-09-0 ]
  • [ 959992-62-2 ]
Reference: [1] Patent: EP2341052, 2011, A1,
[2] Patent: CN108623615, 2018, A,
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