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[ CAS No. 923595-58-8 ] {[proInfo.proName]}

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Chemical Structure| 923595-58-8
Chemical Structure| 923595-58-8
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Product Details of [ 923595-58-8 ]

CAS No. :923595-58-8 MDL No. :MFCD13193346
Formula : C6H3ClIN3 Boiling Point : -
Linear Structure Formula :- InChI Key :OPASGSRWIMSJGT-UHFFFAOYSA-N
M.W : 279.47 Pubchem ID :46941644
Synonyms :

Calculated chemistry of [ 923595-58-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
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 : 50.71
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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.111 mg/ml ; 0.000398 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 1.77 mg/ml ; 0.00633 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.148 mg/ml ; 0.000528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.14

Safety of [ 923595-58-8 ]

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 [ 923595-58-8 ]

* 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 [ 923595-58-8 ]
  • Downstream synthetic route of [ 923595-58-8 ]

[ 923595-58-8 ] Synthesis Path-Upstream   1~2

  • 1
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YieldReaction ConditionsOperation in experiment
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (200 mg, 1.30 mmol) in DMF (2 mL) was added N-iodosuccinimide (322 mg, 1.86 mmol). The reaction was stirred at rt overnight, then diluted with EtOAc (100 mL), and washed with H2O (50 mL), saturated Na2S2O3 aqueous solution (50 mL) and brine (50 mL). The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as a pale yellow solid (390 mg, 100percent). [0309] MS (ESI, pos. ion) m/z: 279.9 [M+H]+. [0310] 1H NMR (400 MHz, CDCl3) δ (ppm): 8.57 (d, J=7.2 Hz, 1H), 8.16 (s, 1H), 6.86 (d, J=7.2 Hz, 1H)
96% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2 h; To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (1.00 g, 6.51 mmol) in DMF (13 mL) was added portionwise N-iodosuccinamide (1.61 g, 7.16 mmol) at room temperature.
The reaction mixture was stirred for 2 hours at room temperature.
After addition of water, the mixture was stirred for further 30 min at room temperature.
A precipitated solid was collected by filtration and dried under vacuum to afford 5-chloro-3-iodopyrazolo[1,5-a]pyrimidine (1.74 g, 96percent) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): δ 7.15 (1H, d, J=7.2 Hz), 8.34 (1H, s), 9.17 (1H, d, J=7.2 Hz).
89% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 4 h; N-Iodosuccinimide (1.61 g, 7.16 mmol) was added to a solutionof 5-chloropyrazolo[1,5-a]pyrimidine (7) (1 g, 6.51 mmol) in anhydrousDMF (10 mL). After stirring at RT for 4 h the reaction was poured into 10percent sodium thiosulfate (75 mL). The resulting precipitate was isolated via filtration and dried (Whatman PS1 filterpaper) to give 19 as a pale brown solid (1.62 g, 89percent). 1H NMR δH (d6-DMSO, 300 MHz), 9.19 (d, J 7.2, 1H), 8.38 (s, 1H), 7.18 (d, J7.2, 1H). LC–MS tR 6.37 min; LC254 99percent; m/z 280.1/282.0 [M+H].This was used without further purification.
Reference: [1] Patent: US2014/234254, 2014, A1, . Location in patent: Paragraph 0308; 0309; 0310
[2] Patent: US2016/168156, 2016, A1, . Location in patent: Paragraph 0439; 0441; 0442
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6280 - 6296
[4] Patent: WO2007/13673, 2007, A1, . Location in patent: Page/Page column 31
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Reference: [1] Patent: US2016/168156, 2016, A1,
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