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[ CAS No. 112758-40-4 ] {[proInfo.proName]}

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Chemical Structure| 112758-40-4
Chemical Structure| 112758-40-4
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Product Details of [ 112758-40-4 ]

CAS No. :112758-40-4 MDL No. :MFCD01313822
Formula : C5H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :NWDMGTFNIOCVDU-UHFFFAOYSA-N
M.W : 110.11 Pubchem ID :2760056
Synonyms :

Calculated chemistry of [ 112758-40-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.94
TPSA : 45.75 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) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.46
Log Po/w (XLOGP3) : 0.08
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 0.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.97
Solubility : 11.8 mg/ml ; 0.107 mol/l
Class : Very soluble
Log S (Ali) : -0.59
Solubility : 28.0 mg/ml ; 0.254 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.51
Solubility : 3.42 mg/ml ; 0.031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 112758-40-4 ]

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 [ 112758-40-4 ]

* 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 [ 112758-40-4 ]
  • Downstream synthetic route of [ 112758-40-4 ]

[ 112758-40-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 68-12-2 ]
  • [ 110-20-3 ]
  • [ 112758-40-4 ]
YieldReaction ConditionsOperation in experiment
32%
Stage #1: at 0℃; for 1.5 h;
Stage #2: at 0 - 70℃;
Stage #3: With sodium hydroxide In waterCooling with ice
To cool DMF (65 ml_) at 0 3C, POCI3 (39 ml_) was added drop wise for 30 minutes, and maintained at 0 3C for 1 hour. To the mixture was added acetone semicarbazole (1 3 g, 1 14 mmol) portionwise at 0 3C and maintained at 70 9C for 4 hours. The mixture was poured over crushed ice (500 g), neutralized using 10percent NaOH solution and extracted using ethyl acetate (3x15OmL). The combined organic layers were washed with water (2x100 mL), saturated aqueous NaCI (100 mL), dried over anhydrous Na2SO4 and concentrated to obtain a crude product, which was purified by column chromatography (60-120 mesh silica gel) using 2-4percent methanol in chloroform as eluents to afford 3-methyl-1 H-pyrazole-4- carbaldehyde (4 g, 32percent) as solid. 1H NMR (CDCI3) δ 9.96 (s, 1 H), 8.0 (s, 1 H), 2.6 (s, 3H).
Reference: [1] Patent: WO2009/144554, 2009, A1, . Location in patent: Page/Page column 37
[2] Synthesis, 1997, # 10, p. 1140 - 1142
  • 2
  • [ 4344-87-0 ]
  • [ 68-12-2 ]
  • [ 112758-40-4 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 4, p. 507 - 516
  • 3
  • [ 1006514-65-3 ]
  • [ 955965-18-1 ]
  • [ 112758-40-4 ]
  • [ 112758-40-4 ]
  • [ 79-10-7 ]
Reference: [1] Russian Journal of General Chemistry, 2014, vol. 84, # 4, p. 793 - 795[2] Zh. Obshch. Khim., 2014, vol. 84, # 4, p. 793 - 795,3
  • 4
  • [ 3934-20-1 ]
  • [ 112758-40-4 ]
  • [ 1448307-66-1 ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14 h; To a solution of ethyl 3-methyl-iH-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N- dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature. The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (x2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 2 as a white solid (5.47 g, 42 percent); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCls) δ 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, / = 5.4 Hz), 7.87 (1H, d, / = 5.4 Hz), 2.59 (s, 3H).
42% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14 h; Preparation of 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; Intermediate 1
To a solution of ethyl 3-methyl-1H-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N-dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature.
The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC).
The reaction mixture was diluted with ethyl acetate and washed with brine (*2).
The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo.
The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 1 as a white solid (5.47 g, 42percent); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCl3) δ 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, J=5.4 Hz), 7.87 (1H, d, J=5.4 Hz), 2.59 (s, 3H).
Reference: [1] Patent: WO2013/109882, 2013, A1, . Location in patent: Page/Page column 55
[2] Patent: US2015/111883, 2015, A1, . Location in patent: Paragraph 0218; 0219
  • 5
  • [ 3934-20-1 ]
  • [ 112758-40-4 ]
  • [ 1448307-66-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4441 - 4446
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