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[ CAS No. 705263-10-1 ] {[proInfo.proName]}

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Chemical Structure| 705263-10-1
Chemical Structure| 705263-10-1
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Product Details of [ 705263-10-1 ]

CAS No. :705263-10-1 MDL No. :MFCD09832894
Formula : C6H4BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :VDHTXLUCUNPVLO-UHFFFAOYSA-N
M.W :198.02 Pubchem ID :22236701
Synonyms :

Calculated chemistry of [ 705263-10-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.69
TPSA : 30.19 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) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : 1.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.833 mg/ml ; 0.0042 mol/l
Class : Soluble
Log S (Ali) : -1.24
Solubility : 11.3 mg/ml ; 0.0571 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.533 mg/ml ; 0.00269 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 705263-10-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 705263-10-1 ]

* 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 [ 705263-10-1 ]
  • Downstream synthetic route of [ 705263-10-1 ]

[ 705263-10-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride In ethanol; water at 0 - 20℃; for 2 h; Will V be non-material (15 · lg, lOOmmol)And the formula II is not material (8.3g, lOOmmol)Placed in a 250 ml round bottom flask,Add 120 ml of ethanol,Cooled to 0 ° C, add 12ml concentrated hydrochloric acid, return to room temperature, stirring 2h,The reaction precipitated a pale yellow solid. After direct filtration, the cake was washed with saturated NaHC03 solution and then washed with water.After drying, 17 g of the intermediate represented by formula VI was obtained. The yield of the intermediate represented by formula VI was calculated to be 86percent.
30% for 2 h; Reflux The 3-aminopyrazole (2.0g, 23.9 mmol) and 20 mL of ethanol were added 100 mL three-neck flask, and stirred to dissolve, then 2-bromo-malonaldehyde (2.4 g, 16.0 mmol) was added in the flask. The system presents a reddish brown after the mixture was heated under reflux for 2 h. The reaction was cooled to room temperature and the organic solvent is evaporated to dryness. The residue was purified by column chromatography: gel (eluent petroleum ether / ethyl acetate). Pale yellow crystalline solid, yield: 30percent. 1H NMR (CDCl3, 400 MHz, δ ppm): 8.50 (d, J = 3.3 Hz, 1H), 7.99 (dd, J = 9.2, 1.5 Hz, 1H), 7.82 (s, 1H), 7.13 (dd, J = 9.2, 4.4 Hz, 1H). ESI-MS(m/z): 197.3 [M+H]+.
Reference: [1] Patent: CN105130991, 2017, B, . Location in patent: Paragraph 0037; 0041-0043
[2] Patent: WO2014/138088, 2014, A1, . Location in patent: Page/Page column 60
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4388 - 4392
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5830 - 5835
  • 2
  • [ 1820-80-0 ]
  • [ 2065-75-0 ]
  • [ 705263-10-1 ]
YieldReaction ConditionsOperation in experiment
58% at 20℃; for 3 h; At room temperature,3-amino-1H-pyrazole (120 mmol, 10 g)A solution in 50 ml of anhydrous acetic acid was added dropwise to bromomalonaldehyde (120 mmol, 18.9 g)In a suspension of 50 mL of anhydrous acetic acid,The resulting brown solution was stirred at room temperature for 3 hours.Evaporating acetic acid under reduced pressure,Adding chloroform to the residue;The organic phase is saturated with NaHCO3 solution,Washed with brine and dried over sodium sulfate.After the column, the product was obtained (14g, 58percent).
58% With acetic acid In ethanol at 80℃; for 1.5 h; Synthesis of 4-[6-(4-Piperazin-l-ylphenyl)pyrazolo[l ,5-a]pyrimidin-3-yllquinoline hydrochloride salt (13 HCH; A mixture of 2-bromomalondialdehyde (1.5 g, 10 mmol) and lH-pyrazol-3- ylamine (4b, 0.83 g, 10 mmol) in a mixture of EtOH (15 mL) and acetic acid (5 mL) was heated at 80 °C for 1.5 h. The reaction mixture was concentrated and the resulting residue purified by column chromatography using hexane/EtOAc (5:1 ) to give 15a (1.15 g, 58percent yield) as light yellow crystals.
42% at 20℃; for 3 h; Preparation 16-Bromo-pyrazolo[1 ,5-a]pyrimidine[00117] A solution of 3-amino-1 H-pyrazole (120 mmol, 10g) in 50ml of anhydrous acetic acid is added dropwise to a suspension of bromomalonaldehyde (120 mmol, 18.9 g) in 50 mL anhydrous acetic acid at room temperature. The resulting brown solution is stirred at room temperature for 3 hours, acetic acid is evaporated at reduced pressure and chloroform is added to the residue. The organic phase is washed with saturated solution of NaHCO3, brine, and dried over sodium sulfate. The product is purified by flash column chromatography (CH2CI2 : Et3N 100 : 0.5 as eluent, Rf=0.3) to yield the title compound (5 g, 42percent).
11% for 2 h; Heating / reflux Dissolve bromomalonaldehyde (Aldrich; 2.5 g, 16.5 mmol) and 3-aminopyrazole (Aldrich; 1.38 g, 16.5 mmol) in glacial acetic acid (25 ML) and reflux the resulting mixture under nitrogen for 2 h. Concentrate under reduced pressure. Dissolve the residue in absolute methanol (150 mL), vacuum filter through a pad diatomaceous earth and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from neat hexane to 50percent ethyl acetate/50percent hexane to obtain 365 mgs (11percent) of the subtitled compound as a light yellow solid. High Resolution Mass Spectrum: 197.9674 (M+1).

Reference: [1] Patent: CN108586464, 2018, A, . Location in patent: Paragraph 0031; 0038; 0039
[2] Patent: WO2009/114180, 2009, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2011/15343, 2011, A1, . Location in patent: Page/Page column 38-39
[4] Patent: WO2004/50659, 2004, A1, . Location in patent: Page 72
[5] Patent: WO2008/78100, 2008, A2, . Location in patent: Page/Page column 111-112
[6] Patent: WO2004/74290, 2004, A1, . Location in patent: Page 83
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3248 - 3252
  • 3
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
2.1% at 20℃; Heating / reflux A solution of 1 H-pyrazol-5-amine x79 (25 g, 1 eq, 0.3 mol) and bromomalonaldehyde x9 (45.4 g, 1 eq, 0.3 mol) ethanol (250 ml) is refluxed for 2 hours. After cooling, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude is purified using chiral chromatography affording 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (yield: 2.1 percent; LC-MS (MH+): 198/200) and 6-bromopyrazolo[1 ,5-a]pyrimidine x81 (yield: 13.8 percent; LC-MS (MH+): 198/200).
Reference: [1] Patent: WO2006/128692, 2006, A2, . Location in patent: Page/Page column 86
  • 4
  • [ 1820-80-0 ]
  • [ 20591-60-0 ]
  • [ 705263-10-1 ]
Reference: [1] Patent: WO2009/14620, 2009, A1, . Location in patent: Page/Page column 36; 24
  • 5
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
2.1% at 20℃; Heating / reflux A solution of 1 H-pyrazol-5-amine x79 (25 g, 1 eq, 0.3 mol) and bromomalonaldehyde x9 (45.4 g, 1 eq, 0.3 mol) ethanol (250 ml) is refluxed for 2 hours. After cooling, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude is purified using chiral chromatography affording 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (yield: 2.1 percent; LC-MS (MH+): 198/200) and 6-bromopyrazolo[1 ,5-a]pyrimidine x81 (yield: 13.8 percent; LC-MS (MH+): 198/200).
Reference: [1] Patent: WO2006/128692, 2006, A2, . Location in patent: Page/Page column 86
  • 6
  • [ 705263-10-1 ]
  • [ 933754-38-2 ]
Reference: [1] Patent: CN108586464, 2018, A,
  • 7
  • [ 705263-10-1 ]
  • [ 1765-93-1 ]
  • [ 1036762-04-5 ]
Reference: [1] Patent: WO2008/78100, 2008, A2, . Location in patent: Page/Page column 113
  • 8
  • [ 705263-10-1 ]
  • [ 1062368-62-0 ]
Reference: [1] Patent: WO2009/114180, 2009, A1,
  • 9
  • [ 705263-10-1 ]
  • [ 1109284-33-4 ]
Reference: [1] Patent: WO2009/14620, 2009, A1, . Location in patent: Page/Page column 36; 24
  • 10
  • [ 705263-10-1 ]
  • [ 1435615-18-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3248 - 3252
  • 11
  • [ 705263-10-1 ]
  • [ 1432597-26-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3248 - 3252
[2] Patent: WO2014/138088, 2014, A1,
[3] Patent: CN105130991, 2017, B,
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