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[ CAS No. 309740-49-6 ] {[proInfo.proName]}

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Chemical Structure| 309740-49-6
Chemical Structure| 309740-49-6
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Product Details of [ 309740-49-6 ]

CAS No. :309740-49-6 MDL No. :MFCD02110822
Formula : C6H7N3O4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :ANWHCLPGJQUYRX-UHFFFAOYSA-N
M.W : 185.14 Pubchem ID :1255549
Synonyms :

Calculated chemistry of [ 309740-49-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.59
TPSA : 89.94 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 0.25
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -1.0
Log Po/w (SILICOS-IT) : -1.88
Consensus Log Po/w : -0.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.23
Solubility : 10.9 mg/ml ; 0.0586 mol/l
Class : Very soluble
Log S (Ali) : -1.7
Solubility : 3.7 mg/ml ; 0.02 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.26
Solubility : 103.0 mg/ml ; 0.555 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.2

Safety of [ 309740-49-6 ]

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

Application In Synthesis of [ 309740-49-6 ]

* 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.

  • Upstream synthesis route of [ 309740-49-6 ]
  • Downstream synthetic route of [ 309740-49-6 ]

[ 309740-49-6 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
33% With potassium carbonate In acetone at 70℃; for 2 h; Compound 6 and 6A: To a mixture containing 5 (3.1 g, 18.1 mmol) and potassium carbonate (5.0 g, 36.2 mmol) in 60 mL of acetone was added methyl iodide (2.2 mL, 36.2 mmol). The resulting solution was heated and stirred at 70° C. for 2 hours. After the reaction mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate (.x.3). The combined organics were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 20percent ethyl acetate in hexanes as the eluent to afford 6 (1.1 g, 33percent) as white solid. 1H NMR (d6-DMSO) δ 3.96 (s, 3H) 3.98 (s, 3H) 8.36 (s, 1H); ES (+) MS m/e=186 (M+1) and using 30percent ethyl acetate in hexanes to afford 6A (2.2 g, 66percent) as white solid. 1H NMR (d-CDCl3) δ 3.98 (s, 3H) 4.00 (s, 3H) 8.13 (s, 1H); ES (+) MS m/e=186 (M+1).
Reference： [1] Patent: US2007/27166, 2007, A1, . Location in patent: Page/Page column 79
[2] Patent: EP1956009, 2008, A1, . Location in patent: Page/Page column 40
[3] Patent: EP1970373, 2008, A1, . Location in patent: Page/Page column 91
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YieldReaction ConditionsOperation in experiment
61% With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20℃; To a solution of 14 (5 g, 29.2 mmol), methanol (5.93 mL, 146mmol) and tributylphosphine (14.6 mL, 58.4 mmol) in toluene(500 mL) was added 1,10-(azodicarbonyl)dipiperidine (14.8 g,58.4 mmol) at room temperature. The mixture was stirred at roomtemperature overnight. The insoluble material was removed by filtration,and the filtrate was partitioned between EtOAc and water.The organic layer was separated, washed with aqueous saturatedNaHCO3 and brine, dried over Na2SO4, filtered, and concentratedin vacuo. The residue was purified by column chromatography (silicagel, 30 g, eluted with 0–70percent EtOAc in hexane) to give 15b (3.28g, 61percent yield) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) d 4.03(3H, s), 4.03 (3H, s), 8.02 (1H, s).
Reference： [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2452 - 2465
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YieldReaction ConditionsOperation in experiment
34.5% With potassium carbonate In acetone at 50℃; for 4 h; 4-Nitro-lH-pyrazole-3-carboxylic acid methyl ester (3.4 g, 19.9 mmol) was dissolved in acetone (50 mL)Methyl iodide (5.7 g, 40.22 mmol) and potassium carbonate (5.5 g, 39.9 mmol)Heated to 50 ° C,Reaction for 4 hours.Cooled to room temperature,filter,The filtrate was concentrated in vacuo,The residue was purified by silica gel column chromatography (petroleum ether: 1: ethyl acetate = 2) to give the product(1.27 g, yield: 34.5percent).
Reference： [1] Patent: CN107226807, 2017, A, . Location in patent: Paragraph 0274-0276
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YieldReaction ConditionsOperation in experiment
54% With potassium carbonate In acetone at 0 - 70℃; Inert atmosphere To a solution of 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (3.1 g, 18.1 mmol) in dry acetone (2 ml) was added K2C03 (5 g, 36.2 mmol) at 25°C. The reaction mixture was cooled to 0°C, and methyl iodide (2.2 ml, 36.3 mmol) was added. The temperature was again raised to 25°C, and then heated to 70°C for 2 hrs. The solvent was removed in vacuo The residue was diluted with EtOA and washed with water and with brine, dried (Na2S04), filtered, and concentrated. The crude product was purified by column chromatography over silica gel. Elution with 20percent EtOAc/hexane) gave the undesired isomer 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid methyl ester (1 g, 30percent), subsequent elution with 40percent EtOAc/hexane provided the desired isomer l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (1.8 g, 54percent).
53% With caesium carbonate In N,N-dimethyl-formamideInert atmosphere Preparative Example 7
4-nitro-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester
340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes.
The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine.
The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure.
The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 195 mg (53percent) of the title compound and 110 mg (30percent) of the compound of Preparative Example 13.
1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H), 4.02 (s, 3H), 8.15 (s, 1H).
Mass: 185 (M+)
; 340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 110 mg (30percent) of the title compound and 195 mg (53percent) of the compound of Preparative Example 7.1H NMR (300 MHz, CDCl3) δ 4.03 (s, 3H), 4.04 (s, 3H), 8.03 (s, 1H).
53% With caesium carbonate In N,N-dimethyl-formamide for 0.5 h; 340 mg (1.99 mM) of 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane : ethyl acetate = 2 : 1), to obtain 195 mg (53percent) of the title compound and 110 mg (30percent) of the compound of Preparative Example 13. 1H νMR(300MHz, CDCl3) δ 4.00(s, 3H), 4.02(s, 3H), 8.15(s, IH).Mass : 185(M+); 340 mg (1.99 mM) of 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced EPO <DP n="31"/>pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane : ethyl acetate = 2 : 1), to obtain 110 mg (30percent) of the title compound and 195 mg (53percent) of the compound of Preparative Example 7.1H NMR(SOOMHZ, CDCl3) δ 4.03(s, 3H), 4.04(s, 3H), 8.03(s, IH).
28% With potassium carbonate In acetone at 30℃; for 5 h; Reference Example 20
Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate
A mixture of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (2.0 g, 11.7 mmol), methyl iodide (2.0 g, 14.0 mmol), potassium carbonate (1.62 g, 11.7 mmol) and acetone (60 mL) was stirred at 30° C. for 5 hr.
The mixture was diluted with water, and extracted with chloroform.
The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1-1:1) to give the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate (Rf value 0.43) (0.95 g, yield 44percent) and the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (Rf value 0.71) (0.61 g, yield 28percent).
44% With potassium carbonate In acetone at 30℃; for 5 h; A mixture of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (2.0 g, 11.7 mmol), methyl iodide (2.0 g, 14.0 mmol), potassium carbonate (1.62 g, 11.7 mmol) and acetone (60 mL) was stirred at 30°C for 5 hr. The mixture was diluted with water, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1 - 1:1) to give the title compound, methyl 1-methyl-4-nitro-1-pyrazole-3-carboxylate (Rf value 0.43) (0.95 g, yield 44percent) and the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (Rf value 0.71) (0.61 g, yield 28percent). Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate 1H-NMR (CDCl3):δ 3.99(3H, s), 4.01(3H, s), 8.13(1H, s). Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate 1H-NMR (CDCl3):δ 4.02(3H, s), 4.03(3H, s), 8.01 (1H, s).

Reference： [1] Patent: WO2011/154327, 2011, A1, . Location in patent: Page/Page column 136; 137
[2] Patent: US2010/63106, 2010, A1, . Location in patent: Page/Page column 11;13
[3] Patent: WO2008/51047, 2008, A1, . Location in patent: Page/Page column 25; 28-29
[4] Patent: US2009/156582, 2009, A1, . Location in patent: Page/Page column 30
[5] Patent: EP1847531, 2007, A1, . Location in patent: Page/Page column 43
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YieldReaction ConditionsOperation in experiment
31% With cyanomethylenetributyl-phosphorane In toluene at 110℃; for 0.5 h; Sealed tube; Microwave irradiation General procedure: The reaction was performed in 2 batches. In a sealed tube, cyanomethylenetributyl phosphorane (9.28 mL, 35.40 mmol) was added to a solution of 3-methyl-5-nitro-lH- pyrazole (1.50 g, 1 1.80 mmol) and 3-hydroxymethyl-3-methyloxethane (3.53 mL, 35.40 mmol) in toluene (100 mL). The solution was heated at 60 °C for 18 h. The 2 batches were combined and the solvent was evaporated in vacuo. The residue (black oil) was purified by column chromatography on silica gel (irregular SiOH, 15-40 μιη, 330 g, liquid loading on DCM, mobile phase: heptane/EtOAc, gradient from 90: 10 to 50:50). The fractions containing the product were combined and evaporated to dryness to give 3.95 g of intermediate 303 (79percent yield, orange oil) directly used as it in the next step.
Reference： [1] Patent: WO2018/2217, 2018, A1, . Location in patent: Page/Page column 299; 306
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YieldReaction ConditionsOperation in experiment
8.62 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; Cooling with ice A)
Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate
To a suspension of 4-nitro-1H-pyrazole-3-carboxylic acid (37 g) and potassium carbonate (97.6 g) in DMF (600 mL), dimethyl sulfate (71.2 g) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 16 hours.
The reaction mixture was poured to water, followed by extraction with ethyl acetate.
The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (8.62 g).
1H NMR (400 MHz, CDCl3) δ 4.02 (3H, s), 4.03 (3H, s), 8.01 (1H, s).
Reference： [1] Patent: EP3287441, 2018, A1, . Location in patent: Paragraph 0305
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YieldReaction ConditionsOperation in experiment
83% for 16 h; Heating / reflux [0227] To a solution of l-methyl-4-nitro-lH-pyrazole-5-carboxylic acid (2 g, for the synthesis of l-methyl-4-nitro-lH-pyrazole-5-carboxylic acid, see Perevalov, V. P., et. al.; Chem. Het. Compounds 19; 12; 1983; 1326-1330) in methanol (20 mL), was added HCl (g). The resulting solution was allowed to react, with stirring, for 16 h at reflux. The mixture was concentrated to give methyl l-methyl-4-nitro-lH-pyrazole-5- carboxylate as a yellow oil (1.8 g, 83percent). LCMS: 185 (M+H) +. Step 2: Methyl 4-amino-l-methyl-lH-pyrazole-5-carboxylate
Reference： [1] Patent: WO2009/26241, 2009, A1, . Location in patent: Page/Page column 66-67
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Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
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Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
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Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
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