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[ CAS No. 16461-94-2 ] {[proInfo.proName]}

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Chemical Structure| 16461-94-2
Chemical Structure| 16461-94-2
Structure of 16461-94-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16461-94-2 ]

CAS No. :16461-94-2 MDL No. :MFCD00082728
Formula : C3H4BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :OELYMZVJDKSMOJ-UHFFFAOYSA-N
M.W : 161.99 Pubchem ID :140079
Synonyms :

Calculated chemistry of [ 16461-94-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 30.69
TPSA : 54.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.54
Log Po/w (XLOGP3) : 0.56
Log Po/w (WLOGP) : 0.76
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.73
Solubility : 3.05 mg/ml ; 0.0188 mol/l
Class : Very soluble
Log S (Ali) : -1.28
Solubility : 8.48 mg/ml ; 0.0524 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.72
Solubility : 3.1 mg/ml ; 0.0191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 16461-94-2 ]

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 [ 16461-94-2 ]

* 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 [ 16461-94-2 ]
  • Downstream synthetic route of [ 16461-94-2 ]

[ 16461-94-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 16461-94-2 ]
  • [ 102-52-3 ]
  • [ 55405-67-9 ]
YieldReaction ConditionsOperation in experiment
39% for 4 h; Reflux A. A solution of 3-amino-4-bromopyrazole (2.0 g, 12 mmol) and 1 ,1 ,3,3- tetramethoxypropane (4.1 mL, 25 mmol) in acetic acid (5 mL) was heated at reflux for 4 h. Water (2 mL) was added and the mixture heated at reflux for a further 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in methanol. The solid thus obtained was washed with cold methanol, ethyl acetate, and hexanes to provide 3-bromopyrazolo[1 ,5-a]pyrimidine as a brownish solid in 39percent yield (0.953 g): 1H NMR (300 MHz, DMSO-d6) £9.13 (d, J = 6.5 Hz, 1 H), 8.61 (s, 1 H), 8.35 (s, 1 H), 7.19-7.02 (m, 1 H); MS (ES+) m/z 197.9 (M + 1), 199.9 (M + 1).
Reference: [1] Patent: WO2013/64984, 2013, A1, . Location in patent: Page/Page column 66
[2] Patent: WO2009/85913, 2009, A1, . Location in patent: Page/Page column 68; 69
  • 2
  • [ 1820-80-0 ]
  • [ 16461-94-2 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With bromine In acetic acid at 0 - 5℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water
At 0-50C, a solution of 3-amino pyrazole (120mmol) in AcOH (22mL) was slowly added a solution of Br2 in AcOH (22mL) over a period of 2h. The reaction was complete immediately after the addition of Br2 solution (120mmol). To the reaction mixture was added CCl4 (8mL), stirred for 30min at rt. The precipitated solid was filtered and washed with additional CCl4 (8mL). The solid so obtained was dissolved in water (40 mL), adjusted to pH ~7.5 (using aq. NaHCO3 solution) and the precipitated solid was filtered and washed with water (8mL). The combined filtrates were also adjusted to pH ~8 (aq. Na2CO3 solution), extracted with EtOAc (80OmL), washed with brine solution <n="70"/>(20OmL), dried (Na2SO4), filtered and evaporated to obtain the desired compound as a yellow solid. The crude compound was stirred with CCl4 (2OmL), filtered and washed with acetone (5mL) and CCl4 (8mL), and dried under vacuum. The product was obtained as a pale yellow solid (17.2 g, 88 percent yield). TLC system: DCM/MeOH (9: 1). Rf value: 0.5. (M + H): 162.3.
Reference: [1] Patent: WO2009/85913, 2009, A1, . Location in patent: Page/Page column 68-69
  • 3
  • [ 16461-94-2 ]
  • [ 81267-58-5 ]
  • [ 945376-95-4 ]
YieldReaction ConditionsOperation in experiment
61.5% With acetic acid In ethanol for 12 h; Heating / reflux Step 2 :4-(3-Bromopyrazolori,5-a1pyrimidin-6-yl)phenol; A mixture of 3-(dimethylamino)-2-(4-hydroxyphenyl)acrylaldehyde (5.00 g, 0.026 mol), 3-amino-4- bromopyrazole (4.23 g, 0.026 mol), 84 mL of ethanol and 4.2 mL of acetic acid was refluxed for 12 h. The mixture was cooled and the precipitate filtered off, washed twice with water and a small amount of ethanol, then dried in vacuum at 40-500C for 8 h. to give the desired phenol. Yield: 4.66 g (61.5percent).
Reference: [1] Patent: WO2007/85873, 2007, A1, . Location in patent: Page/Page column 17-18
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