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[ CAS No. 823-85-8 ] {[proInfo.proName]}

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Chemical Structure| 823-85-8
Chemical Structure| 823-85-8
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Quality Control of [ 823-85-8 ]

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Product Details of [ 823-85-8 ]

CAS No. :823-85-8 MDL No. :MFCD00012942
Formula : C6H8ClFN2 Boiling Point : -
Linear Structure Formula :FC6H4NHNH3Cl InChI Key :FEKUXLUOKFSMRO-UHFFFAOYSA-N
M.W : 162.59 Pubchem ID :69981
Synonyms :

Calculated chemistry of [ 823-85-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.57
TPSA : 38.05 ?2

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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 2.13
Log Po/w (SILICOS-IT) : 0.79
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.23
Solubility : 0.948 mg/ml ; 0.00583 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.59 mg/ml ; 0.00976 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.33
Solubility : 0.766 mg/ml ; 0.00471 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 823-85-8 ]

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

Application In Synthesis of [ 823-85-8 ]

* 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 [ 823-85-8 ]

[ 823-85-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 823-85-8 ]
  • [ 78-93-3 ]
  • [ 526-47-6 ]
  • 2
  • [ 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.

  • 3
  • [ 1118-61-2 ]
  • [ 823-85-8 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
69% General procedure: In a 2-5mL microwave vial containing a stir bar, 3-aminocrotonitrile (164 mg, 2mmol) and 5 mL of 1M HCl were combined with stirring to give a 0.4 M solution of starting material. Next, phenylhydrazine (216 mg, 2 mmol) was added to the solution. The microwave vial was then sealed with an aluminum cap and irradiated in the microwave reactor at 150 C for 10 m with the absorbance set to “very high.” After cooling, the orange sludge-containing heterogeneous solution was basified with 10% NaOH and was sonicated for 5 m to produce a visible solid precipitate. The precipitate was filtered, washed twice with D.I. water, and then dried to yield the product as a light orange solid (292 mg, 84% yield). For compounds that do not readily precipitate, the product can be isolated by extracting the basic aqueous layer 3x with dichloromethane (DCM). The combined organic layers are dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the product.
With hydrogenchloride; In water; 5-Amino-1-(4-fluorophenyl)-3-methyl-pyrazole 4-Fluorophenylhydrazine HCl (60.0 g.) 175 ml. water, 70 ml. concentrated hydrochloric acid and 28.8 g. 3-amino-2-butene nitrile were refluxed one hour. The solution was cooled and made basic with concentrated ammonia. The solid was filtered and crystallized from ether to get 51.05 g. product, mp 108-110, which was converted to the HCl salt mp 227-229 Analyzed for C10 H10 FN3.HCl: Theoretical; C=52.76, H=4.87, N=18.47 Found; C=52.96, H=4.87, N=18.36
With hydrogenchloride; In water; 5-Amino-1-(4-fluorophenyl)-3-methyl-pyrazole 4-Fluorophenylhydrazine HCl (60.0 g.) 175 ml. water, 70 ml. concentrated hydrochloric acid and 28.8 g. 3-amino-2-butene nitrile were refluxed one hour. The solution was cooled and made basic with concentrated ammonia. The solid was filtered and crystallized from ether to get 51.05 g. product, mp 108-110, which was converted to the HCl salt mp 227-229 Analyzed for C10 H10 FN3 ·HCl: Theoretical; C=52.76, H=4.87, N=18.47. Found; C=52.96, H=4.87, N=18.36.
  • 4
  • [ 823-85-8 ]
  • [ 123-06-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
86% With sodium ethanolate; sodium hydride; In ethanol; at 20℃; for 2h;Heating / reflux; Sodium hydride as a 60% dispersion in mineral oil (5.90 g, 1.2 eq, 0.147 mol.) was added slowly to ethanol (200 ml) at room temperature. To the solution of sodium ethoxide in ethanol was added 4-fluorophenylhydrazine hydrochloride (23.96 g, 1.2 eq, 0.147 mol.), addition of ethoxymethylene malonitrile (15.00 g, 1.0 eq, 0.123 mol.) shortly followed. The reaction mixture was heated to reflux with stirring for 2 hours. The reaction was then allowed to cool to room temperature, once at room temperature diethyl ether (50 ml) was added to the reaction mixture. The resultant precipitate was collected by filtration, washed with diethyl ether (2 x 100 ml) and dried in vacuo to give the title compound as a beige solid (21.5 g, 0.106 mol, 86%). LCMS: [M+H]+=203, Rt = 1.02 min, 100% purity.
46% With triethylamine; In ethanol; at 50℃; for 2h; Example 5A8.7 g (53.5 mmol) of 4-fluorphenylhydrazine hydrochloride was suspended with 6.5 g (53.5 mmol) of ethoxymethylenemalononithle in 13 ml of ethanol, and 22.2 ml (160 mmol) of thethylamine were added. The reaction mixture was heated to 500C for 2 h. After cooling to room temperature the solvent was removed under reduced pressure. The remaining residue was treated with water (25 ml) and extracted three times with ethyl acetate. The organic layer was dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. The remaining residue was <n="60"/>purified by preparative MPLC (SiO2, eluent CH2CI2). 5.0 g (46% of theory) of the product were obtained as an oil, that solidifies over night.LC-MS (Method 1 ): RT = 1.06 minMS (ESI pos): m/z = 203 (M+H)+.
General procedure: A stirred mixture of para-substituted phenylhydrazinehydrochloride (0.025 mol) was dissolved in H2O (30 mL), thenthe pH of the mixture was adjusted to pH 7-8 by the dropwiseaddition of 10% NaOH solution to form the free para-substitutedphenyl hydrazines, which were then refluxed for 3 h with ethoxymethylene malononitrile in an ethanol medium. After completionof the reaction, the reaction mixture was allowed to cool at room temperature, and the solid were filtered under vacuum. The crudeproducts obtained were recrystallized from anhydrous ethanol togive the light yellow solid.
  • 5
  • [ 1191-99-7 ]
  • [ 823-85-8 ]
  • [ 101349-12-6 ]
YieldReaction ConditionsOperation in experiment
65% The following reaction procedure was carried out under an N2-atmosphere due to general laboratory safety considerations. 500g of 4-fluorophenylhydrazine hydrochloride (3.08 mol) were suspended in a mixture of 2.5 1 of 2-methyltetrahydrofuran and an aqueous solution of ammonium chloride [350 g ammonium chloride (6.54 mol) in 4650 ml of water]. The suspension was heated to 70 C whereby the 4- flourophenylhydrazine was completely dissolved in the heterogeneous reaction medium formed by the aqueous solution and the organic solvent. Over a period of 1 h, 215.5 g 2,3-dihydrofuran (3.08 mol) dissolved in 2.4 1 2-methyltetrahydrofuran were added to the heterogeneous reaction medium whilst stirring and after completion of the addition, the reaction mixture was stirred at 70 C for an additional 16 to 24 h. The mixture was then cooled to 50 C, and after 15 minutes without stirring to allow phase separation, the organic and aqueous phase were isolated whilst maintaining the temperature at 50 C. To the organic phase a washing solution consisting of 180 g sodium chloride dissolved in 3375 ml of water was added and the mixture was stirred vigorously for 10 minutes at 50 C. Stirring was stopped and the organic phase was allowed to separate from the aqueous phase during 15 minutes and was then isolated, all of which was done whilst maintaining the temperature at 50 C. The organic solvent was removed from the organic phase at 55 C under reduced pressure (98%) in about 65 % yield.
65% With sulfuric acid; In N,N-dimethyl acetamide; water; at 100℃; for 3h; (4-fluorophenyl)hydrazine hydrochloride (2) (16.26 g, 100 mmol) was dissolved in a mixture of N,N-dimethylacetamide (140 mL) and 4% m/m aqueous H2SO4 (140 mL) and heated to 100 oC. 2,3-dihydrofuran (1a) (100 mmol) was then added dropwise over 5 min, and the solution was stirred for 3h at 100 oC. After cooling to room temperature, the mixture was extracted with EtOAc (3×100 mL), the combined organic layer was washed with H2O (3×100 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5:1, V/V) to give compound 3a as an orange oil (11.64 g, 65 %). MS (ESI) m/z: 178.06 [M-H]-.
  • 6
  • [ 42466-67-1 ]
  • [ 823-85-8 ]
  • [ 138907-68-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: Intermediates 5 was synthesized based on the literature of Stephane L.etal. [27] Dissolve phenylhydrazine hydrochloride with 1.5 equivalents of sodium acetate in ethanol, stir and reflux for 1h, filter to obtain filtrate, then add ethyl (E)-2-cyano-3-ethoxyacrylate, stir and reflux for 1h, then the solution was rotary evaporated until the volume of the solution was reduced by half. After cooling, solids intermediate 5 can be precipitated, then filtered under vacuum. The resulting crude products are subjected to recrystallization purification.
2.65 g In ethanol; at 110℃; To a stirred solution of Step 1 intermediate (2.0 g, 10.14 mmol) in ethanol (20 mL), 4- fluorophenylhydrazine hydrochloride (1.97 g, 12.17 mmol) was added at RT and the reaction mixture was stirred overnight at 110 C. The rection mixture was cooled to RT, solvent were evaporated under reduced pressure and the residue was basified with saturated aqueous sodium bicarbonate solution till pH 9- 10. The mixture was extracted with ethyl acetate (100 mL x 2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained product was purified by silica gel column chromatography to afford 2.65 g of the titled product as a solid. lH NMR (300 MHz, DMSO-d6): delta 1.26 (t, = 7.2 Hz, 3H), 4.21 (q, = 7.2 Hz, 2H), 6.31 (s, 2H), 7.37 (t, = 8.1 Hz, 2H), 7.54-7.57 (m, 2H), 7.69 (s, 1H); APCI (m/z) 250 (M+H)+.
  • 7
  • [ 823-85-8 ]
  • dihydrofuran [ No CAS ]
  • [ 101349-12-6 ]
  • 8
  • [ 3719-45-7 ]
  • [ 823-85-8 ]
  • 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid N'-(4-fluorophenyl)hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;Inert atmosphere; DIPEA (210 mg, 1.63 mmol), 4-fluorophenylhydrazine hydrochloride (132.8 mg, 0.816 mmol) and HATU (310 mg, 0.816 mmol) were added at 0 °C under nitrogen to a stirred solution of <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid</strong> (100 mg, 0.653 mmol) in DMF (2 mL). The reaction mixture was stirred at room temperature for 2 h, quenched with ice-water (10 mL), and extracted with ethyl acetate (2x10 mL). The combined organic layer was washed with water (1 x10 mL), brine (10 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) to afford 50 mg (29percent yield) of the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta: 10.09 (s, 1 H), 8.41 (s, 1 H), 7.87 (dd, J= 9.4 Hz,2.4 Hz,1 H), 7.80 (d, J= 2.56 Hz 1 H), 6.96 (t, J= 8.88 Hz ,2H), 6.77-6.74 (m, 2H), 6.42 (d, J= 9.48 Hz 1 H), 3.48 (s, 3H); LC-MS m/z (M-H): 260.1.
  • 9
  • [ 672-81-1 ]
  • [ 823-85-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine; In ethanol; for 16h;Reflux; 2-(Methoxymethylene)malononitrile (1.00 g, 8.19 mmol), (4-fluorophenyl) hydrazine hydrochloride (1.40 g, 8.61 mmol), triethylamine (1.66 g, 16.4 mmol) and ethanol (50 mE) were added to a 100-mE round-bottom flask fitted with a magnetic stir bar and condenser. The resulting solution was heated at reflux for 16 h. The resulting mixture was concentrated under vacuum. The residue was purified by colunm chromatography eluting with dichloromethane/ methanol (10:1 v/v)to give 5-amino-i-(4-fluorophenyl)-1H- pyrazole-4-carbonitrile (1.00 g, 60%). ECMS: (ESI) mlz 203 [M+H].
  • 10
  • [ 823-85-8 ]
  • [ 107-87-9 ]
  • [ 526-47-6 ]
  • 11
  • [ 823-85-8 ]
  • [ 21168-41-2 ]
  • 2-(4-fluorophenyl)-8-chloro-2H-pyrazolo[4,3-c]quinolin-3(5H)-one [ No CAS ]
  • 12
  • [ 823-85-8 ]
  • [ 5417-82-3 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; at 70℃; for 15h; To a soin. of (4-fluorophenyl)- hydrazine hydrochloride (30.0 g, 185 mmol) in EtOH (100 mE) was added Et3N (56.0 g, 554 mmol) and 2-(ethoxymethyiene)rnaiononitrile (23.66 g, 194 mmoi). After the addition was complete, the reaction mixture was stirred 70C for 15 h. The reaction mixture was cooled to rtand concentrated in vacuo. Then the mixture was extracted with EtOAc (2xiOOmL). The combined organic layer was washed with brine, arid then dried over Na2SO4. filtered and concentrated in vacuo to give crude product. The crude product was purified by silica gel column chromatography (PE/EtOAc 10:1 to 5:1) to give the title compound.
  • 13
  • [ 2469-99-0 ]
  • [ 823-85-8 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 85℃; for 18h; Weighing 0.22 μM of sodium cyanide (2.2 equiv) in 250 ml three-neck bottle in, under ice bath by adding 110 ml THF, then adding 0.1 μM 1 a (1 equiv) and 0.1 μM 1 d (1 equiv), 65 C reflow 12 h. After the reaction, under the ice, with a certain amount of reaction water quenching, adjusting solution PH value to 4 - 5, ethyl acetate extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and get products 2 ad. 250 Ml three-neck bottle is added to the product of the 1st step 2 ad, 100 ml ethanol and 0.9 μM 2 e, 85 C reflow 18 h. Stopping the reaction, steaming and out ethanol, saturated sodium hydroxide solution to adjust the residue for the PH in 9 - 10. DCM extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and, column chromatography purification (dichloromethane: ethyl acetate=20:1) to obtain the product B1.
  • 14
  • [ 86240-43-9 ]
  • [ 823-85-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; for 3h;Reflux; General procedure: Intermediates 20 7 were synthesized according to the literature by Harden etal. [29] A stirred mixture of p-substituted phenylhydrazine hydrochloride was dissolved in 15 EtOH, then the pH was adjusted to alkaline by the addition of 10% 21 NaOH solution to remove the hydrochloride, which were then refluxed for 3h with 22 2-(ethoxymethyl)malononitrile in ethanol. Finally, the mixture is cooled at room temperature, and the intermediates 7 were filtered under vacuum and recrystallized from ethanol to give the pure products.
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; ;