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[ CAS No. 138907-68-3 ] {[proInfo.proName]}

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Chemical Structure| 138907-68-3
Chemical Structure| 138907-68-3
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Product Details of [ 138907-68-3 ]

CAS No. :138907-68-3 MDL No. :MFCD00173917
Formula : C12H12FN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RPPPCKSHIYWAPW-UHFFFAOYSA-N
M.W : 249.24 Pubchem ID :688689
Synonyms :

Calculated chemistry of [ 138907-68-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.17
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.01
TPSA : 70.14 ?2

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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 2.12
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 2.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.199 mg/ml ; 0.000798 mol/l
Class : Soluble
Log S (Ali) : -3.54
Solubility : 0.0727 mg/ml ; 0.000291 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.116 mg/ml ; 0.000463 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 138907-68-3 ]

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 [ 138907-68-3 ]

* 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 [ 138907-68-3 ]

[ 138907-68-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 138907-68-3 ]
  • [ 187949-90-2 ]
YieldReaction ConditionsOperation in experiment
95% Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (22.18 g, 89 mmol) was suspended in 1 N aqueous solution of LiOH (178 ml_, 178 mmol) and methanol (200 ml_). The reaction mixture was refluxed for 17 hours, allowed to cool to room temperature and filtered. The filtrate was acidified to pH=7 with 2N HCI. A solid was collected by filtration and allowed to dry under reduced pressure to afford the title compound as a pale yellow solid (18.64 g, 95 % yield), which was used without further purification.
Intermediate 9: 5-Amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxylic acid. To a suspension of ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxylate (12.1g, 48.5mmol) in ethanol (250ml) was added a solution of lithium hydroxide(5.8g, 242mmol) in water (100ml). The mixture was stirred at reflux for 2.5hr. It was allowed to cool and concentrated to 50% of its volume before 5M hydrochloric acid(47ml) was added. After stirring for 15mins, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added. This was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1 H NMR (400 MHz, DMSO-d6) deltappm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2 H) 6.29 (br. s., 2 H).LC-MS Retention Time 2.20mins, MH+ 222.
Intermediate 9; 5-Amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxyliotac acid; To a suspension of ethyl 5-amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxylate (12 1g, 48 5mmol) in ethanol (250ml) was added a solution of lithium hydroxide (5 8g, 242mmol) in water (100ml) The mixture was stirred at reflux for 2 5 hours It was allowed to cool <n="61"/>and concentrated to 50% of its volume before 5M hydrochloric acid (47ml) was added. After stirring for 15 minutes, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added to the filtrate and the resulting solid was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1H NMR (400 MHz, DMSOd6) delta ppm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2H) 6.29 (br. s., 2H). LC-MS Retention Time 2.20mins, MH+ 222.
With water; In ethanol;Reflux; General procedure: Intermediates 13 6 was synthesized according to the literature by ML Bender [28]. Intermediates 5 was dissolved in a solution of 15 ethanol and 16 potassium hydroxide and refluxed for 2h. After cooling, the pH of the mixture was adjusted to 5-6by the dropwise addition of 10% 17 HCl solution to give an intermediate 13 6, which was filtered under vacuum and recrystallized from ethanol to give the pure products.
To a suspension of ethyl 5-amino-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxylate (12.1g, 48.5mmol) in ethanol (250ml) was added a solution of lithium hydroxide (5.8g, 242mmol) in water (100ml). The mixture was stirred at reflux for 2.5 hours. It was allowed to cool and concentrated to 50% of its volume before 5M hydrochloric acid (47ml) was added. After stirring for 15 minutes, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added to the filtrate and the resulting solid was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1H NMR (400 MHz, DMSO-Cf6) delta ppm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2H) 6.29 (br. s., 2H).LC-MS Retention Time 2.20mins, MH+ 222.
1.8 g With potassium hydroxide; In isopropyl alcohol; at 80℃; for 5h; To a stirred solution of Step 2 intermediate (2.6 g, 10.42 mmol) in isopropyl alcohol (35 mL) was added potassium hydroxide (880 mg, 15.62 mmol) at RT. The mixture was stirred at 80 C for 5h. The solvent was evaporated under reduced pressure and the residue was acidified with nitric acid till pH 2-3. The precipitated solid was filtered, washed with water (40 mL x 2) and dried under vacuum to yield 1.80 g of the titled product as a solid. lH NMR (300 MHz, DMSO- d6): delta 6.27 (s, 2H), 7.36 (t, = 8.4 Hz, 2H), 7.54-7.60 (m, 2H), 7.66 (s, 1H), 12.07 (br s, 1H); APCI (m/z) 220 (M-H)".
In methanol; The solid was filtered off and dried to give <strong>[138907-68-3]5-amino-4-ethylcarboxy-1-(4-fluorophenyl)pyrazole</strong> (28 g) which was suspended in a mixture of 1N lithium hydroxide (100 ml) and methanol (250 ml). The reaction mixture was heated at reflux. After 16 h, the reaction mixture was filtered through a sinter funnel and the filtrate was acidified with 2 N hydrochloric acid (65 ml). The solid was filtered off and dried to give 5-amino-4-carboxy-1-(4-fluorophenyl)pyrazole (21 g).

  • 2
  • [ 371-14-2 ]
  • [ 94-05-3 ]
  • [ 138907-68-3 ]
  • 3
  • [ 823-85-8 ]
  • [ 94-05-3 ]
  • [ 138907-68-3 ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine; In ethanol; for 2.5h;Heating / reflux; Ethyl(ethoxymethylene)cyanoacetate (20.80 g, 123 mmol) and triethylamine (17.1 ml_, 123 mmol) were added to a solution of 4-fluorophenylhydrazine hydrochloride (20.00 g, 123 mmol). The reaction mixture was refluxed for 2.5 hours and allowed to cool to room temperature. A solid was collected by filtration, washed with small amounts of ethanol and EPO <DP n="37"/>heptane and allowed to dry under reduced pressure to afford the title compound as a beige solid (22.18 g, 72 % yield). m/z 250 [M+H]+. 1H NMR (300 MHz, CDCI3) 7.80 (1 H, s), 7.58-7.51 (2H, m), 7.27 (2H, m), 5.27 (2H, br s), 4.33 (2H1 q, J=7.2 Hz), 1.39 (2H, t, J=7.2 Hz).
65% With triethylamine; In ethanol; at 20 - 80℃; for 8h; General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+].
With triethylamine; In ethanol; for 3.5h;Heating / reflux; Intermediate 8: Ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxvlate. To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5hr. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid. 1 H NMR (400 MHz, DMSOd6) deltappm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).
With triethylamine; In ethanol; for 3.5h;Heating / reflux; Intermediate 8; Ethyl 5-amiotano-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxylateTo a stirred suspension of 4-fluorophenylhydraziotane hydrochloride (9 76g, 60mmol) in ethanol (250ml) was added triethylamine (9 2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10 15g, 60mmol) The solution was heated at reflux temperature for 3 5 hours The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12 1g) as an off white solid1H NMR (400 MHz, DMSO-d6) delta ppm 7 70 (s, 1 H) 7 55 (s, J=5 0 Hz, 2H) 7 34 - 7 41 (m, 2 H) 6 34 (br s , 2H) 4 21 (q, J=I 0, 7 0 Hz, 2H) 1 26 (t, J=I 0 Hz, 3H)
With triethylamine; In ethanol; for 3.5h;Heating / reflux; To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5 hours. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid.1H NMR (400 MHz, DMSO-cfe) delta ppm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).
With sodium acetate; In ethanol; at 95℃; for 3.5h; (i) Ethyl-2-cyano-3-(ethyloxy)-2-propenoate (5.0 g, 29.56 mmol), (4- fluorophenyl)hydrazine hydrochloride (4.81 g, 29.56 mmol) and sodium acetate (2.43 g, 29.56 mmol) were dissolved in ethanol (100 ml) and heated for 3.5 hrs at 95C. The mixture was then cooled to room temperature and diluted with dichloromethane (-150 ml) and water (50 ml). The organic layer was separated using a hydrophobic <n="105"/>frit, dried over anhydrous sodium sulphate, filtered and to give ethyl 5-amino-1-(4- fluorophenyl)-1 H-pyrazole-4-carboxylate (6.83 g) as an orange solid. This was used in the next step without further purification.

  • 6
  • [ 138907-68-3 ]
  • 5-amino-4-[3-(2-aminoethyl)benzoyl]-1-(4-fluorophenyl)pyrazole [ No CAS ]
  • 7
  • [ 138907-68-3 ]
  • [ 249937-11-9 ]
  • 9
  • [ 138907-68-3 ]
  • [5-amino-1-(4-fluoro-phenyl)-1<i>H</i>-pyrazol-4-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-methanone [ No CAS ]
  • 11
  • [ 138907-68-3 ]
  • [5-amino-1-(4-fluoro-phenyl)-1<i>H</i>-pyrazol-4-yl]-{3-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-methanone [ No CAS ]
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