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[ CAS No. 29274-24-6 ] {[proInfo.proName]}

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Chemical Structure| 29274-24-6
Chemical Structure| 29274-24-6
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Product Details of [ 29274-24-6 ]

CAS No. :29274-24-6 MDL No. :MFCD04035683
Formula : C6H4ClN3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :WEPRLWNMBTYGGD-UHFFFAOYSA-N
M.W : 153.57 Pubchem ID :21071759
Synonyms :

Calculated chemistry of [ 29274-24-6 ]      Expand+

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) : 1.56
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 : 1.31

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 : 1.7

Safety of [ 29274-24-6 ]

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

Application In Synthesis of [ 29274-24-6 ]

* 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.

  • Downstream synthetic route of [ 29274-24-6 ]

[ 29274-24-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1218935-59-1 ]
  • [ 29274-24-6 ]
  • [ 1223404-89-4 ]
YieldReaction ConditionsOperation in experiment
74% With potassium fluoride; In dimethyl sulfoxide; at 180℃; for 2h; A mixture of 5-chloropyrazolo[1,5-a]pyrimidine (1.18 g, 7.68 mmol), <strong>[1218935-59-1](R)-2-(2,5-difluorophenyl)pyrrolidine</strong> (1.51 g, 8.22 mmol) and KF (2.32 g, 39.1 mmol) in DMSO (26 mL) was heated at 180 C. for 2 hours. The reaction mixture was cooled to room temperature and poured into water. The mixture was stirred for additional 30 min at room temperature. A precipitated solid was collected by filtration and dried under vacuum to afford (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine (1.70 g, 74%) as a yellow solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): delta 1.88-2.06 (3H, m), 2.33-2.45 (1H, m), 3.56-3.70 (1H, m), 3.90-4.00 (1H, m), 5.38 (1H, s), 5.98 (1H, s), 6.10-6.50 (1H, m), 6.85-6.91 (1H, m), 7.10-7.15 (1H, m), 7.26-7.32 (1H, m), 7.81 (1H, d, J=1.6 Hz), 8.60 (1H, s).
68% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 160℃;Sealed tube; Preparation B; Preparation of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazolo?,5-alpyrimidin-3- amine; [00381] Step A: Preparation of (RV5-(2-(2.5-difluorophenyr)pyrrolidin-l- yPpyrazolo [ 1 ,5 -a"|pyrimidine; In a pressure reaction tube was added 5-chloropyrazolo[l,5- a]pyrimidine (4.2 g, 27 mmol), <strong>[1218935-59-1](R)-2-(2,5-difluorophenyl)pyrrolidine</strong> (Preparation A; 5.3 g, 29 mmol), anhydrous n-butanol (5 ml, 55 mmol), and DIEA (9.5 ml, 55 mmol). The yellowish suspension was sealed and heated in an oil bath (160 0C) overnight. The reaction was cooled to ambient temperature, diluted with EtOAc (250 mL), and filtered, rinsing the solid with EtOAc. The filtrate (330 mL) was washed with water (2 x 150 mL), brine (100 mL), concentrated, and purified by silica chromatography, eluting with 2:1 EtOAc/hexanes to give the product as a bright yellowish solid (5.6 g, 68% yield).
  • 2
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 29274-24-6 ]
  • [ 1453176-67-4 ]
YieldReaction ConditionsOperation in experiment
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With triethylamine; at 100.0℃; under 7600.51 Torr;Sealed tube; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr;Sealed tube; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; [0211] Step 3. Pyrazolo[1,5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum.The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 mi m/z = 178.0 [M+Hf?.
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; [0219] Step 3. PyrazolorL5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[l,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 min, m/z = 178.0 [M+H]+.

  • 3
  • [ 1159981-95-9 ]
  • [ 29274-24-6 ]
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