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[ CAS No. 58347-49-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 58347-49-2
Chemical Structure| 58347-49-2
Chemical Structure| 58347-49-2
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Product Details of [ 58347-49-2 ]

CAS No. :58347-49-2 MDL No. :MFCD04035684
Formula : C6H4ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :YCZQHXPIKQHABJ-UHFFFAOYSA-N
M.W : 153.57 Pubchem ID :12281647
Synonyms :

Calculated chemistry of [ 58347-49-2 ]

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 : 38.0
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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.29
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.823 mg/ml ; 0.00536 mol/l
Class : Soluble
Log S (Ali) : -1.52
Solubility : 4.6 mg/ml ; 0.0299 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.747 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 58347-49-2 ]

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 [ 58347-49-2 ]

* 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 [ 58347-49-2 ]
  • Downstream synthetic route of [ 58347-49-2 ]

[ 58347-49-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 29274-23-5 ]
  • [ 58347-49-2 ]
YieldReaction ConditionsOperation in experiment
71% at 90℃; PREPARATION 32
7-Chloropyrazolo[1,5-a]pyrimidine
Pyrazolo[1,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90ºC overnight.
It was poured onto water/ice, extracted with dichloromethane and washed with brine.
It was dried, filtered and concentrated in vacuo.
It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1) to afford the expected compound (83 mg, 71percent).
LRMS (m/z): 154 (M+1)+
1H NMR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71% at 90℃; Pyrazolo[1 ,5-a]pyrimidin-7(4/-/)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83 mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1H NMR (400 MHz, DMSO-d6) δ ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71% at 90℃; PREPARATION 897-Chloropyrazolo[1 ,5-a]pyrimidinePyrazolo[1 ,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88ml, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13ml, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1 H N MR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d , 1 H) 8.52 (d, 1 H)
65% at 90℃; for 2.5 h; 7-Hydroxypyrazolo[1 ,5-a]pyrimidine (60 g, 444 mmol), phosphorus oxychloride (108 mL, 1.15 mol) and dimethylaniline (10.8 mL, 89 mmol) were added to a 250 mL round- bottomed flask and the contents heated to 90 0C. After 2.5 h, the reaction mixture was allowed to cool and was concentrated. The black residue was poured into a beaker containing crushed ice (600 mL) and the resulting solution kept cold using an ice bath. The aqueous solution was extracted with CH2CI2 (3 χ 150 mL) and the combined organic phase was washed with brine (100 mL). The organic phase was dried and concentrated to yield the desired crude product, 7-chloropyrazolo[1 ,5-a]pyrimidine, (44.2 g, 65percent) as a red solid. As the crude product was sufficiently pure to use in the subsequent step, a small sample was purified by column chromatography (33-66percent EtOAc/hexane) to yield an analytical sample as a white solid. HPLC 95percent; 1H NMR (250 MHz, CDCI3) δ 8.41 (d, J = 4.5 Hz, 1 H), 8.25 (d, J = 2.3 Hz, 1 H)1 6.99 (d, J ~ 4.5 Hz, 1 H), 6.84 (d, J = 2.3 Hz, 1 H); 13C NMR (62.9 MHz, CDCI3) δ 150.0, 148.2, 145.4, 139.0, 108.0, 98.7; MS (APCI) 154 [M+Hf.
47% for 72 h; The compound prepared in preparative example 1 (2.4 g, 17.4 mmol) was stirred in POCl3 (54 mL) and N,N-dimethylaniline (6.7 mL) 3 days. The reaction mixture was concentrated, dissolved in saturated NaHCO3 (2000 mL) and extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography using a 2.5percent MeOH in CH2Cl2 solution as eluent (1.3 g, 47percent yield): M+H=154.

Reference: [1] Patent: EP2518071, 2012, A1, . Location in patent: Page/Page column 38
[2] Patent: WO2012/146667, 2012, A1, . Location in patent: Page/Page column 90
[3] Patent: WO2012/146666, 2012, A1, . Location in patent: Page/Page column 160
[4] Patent: WO2007/17678, 2007, A1, . Location in patent: Page/Page column 44
[5] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 610 - 613
[6] Patent: US2007/82901, 2007, A1, . Location in patent: Page/Page column 21
[7] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
  • 2
  • [ 57489-79-9 ]
  • [ 58347-49-2 ]
Reference: [1] Patent: US2012/122838, 2012, A1, . Location in patent: Page/Page column 80
  • 3
  • [ 29274-18-8 ]
  • [ 58347-49-2 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
  • 4
  • [ 197367-75-2 ]
  • [ 58347-49-2 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
  • 5
  • [ 58347-49-2 ]
  • [ 877173-84-7 ]
YieldReaction ConditionsOperation in experiment
76% With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 16 h; A solution of crude 7-chloropyrazolo[1,5-a]pyrimidine (44.2 g, 289 mmol) in dichloromethane (289 mL) was cooled to 0 0C using an ice bath. Λ/-bromosuccinimide(51.4 g, 289 mmol) was added slowly to the solution that was stirred for 16 h at room temperature. The dark orange solution was diluted with dichloromethane (200 mL) and was washed with 10percent potassium carbonate solution (3 x 150 mL) and brine (100 mL).The organic phase was dried and concentrated to give a dark orange solid, which was triturated using MeOH to yield the desired product, 3-bromo-7-chloropyrazolo[1,5- EPO <DP n="46"/>a]pyrimidine (50.9 g, 76percent) as a yellow solid. HPLC 96percent; lH NMR (250 MHz, CDCI3) δ 8.49 (d, J = 5.2 Hz, 1H), 8.25 (s, 1H), 7.07 (d, J = 5.2 Hz, 1H); 13C NMR (62.9 MHz, DMSO) δ 150.4, 145.9, 144.7, 138.5, 109.5, 84.7.
Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
[2] Patent: WO2007/17678, 2007, A1, . Location in patent: Page/Page column 44-45
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