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Chemical Structure| 823-85-8
Chemical Structure| 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 :- 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 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) : -6.16 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.

  • Upstream synthesis route of [ 823-85-8 ]
  • Downstream synthetic route of [ 823-85-8 ]

[ 823-85-8 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 823-85-8 ]
  • [ 399-72-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 135 - 158
  • 2
  • [ 823-85-8 ]
  • [ 123-38-6 ]
  • [ 392-13-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 10, p. 3398 - 3402[2] Angew. Chem., 2016, vol. 128, p. 3459 - 3463,5
  • 3
  • [ 823-85-8 ]
  • [ 78-93-3 ]
  • [ 526-47-6 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8049 - 8055,7
[2] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8049 - 8055
[3] Synthetic Communications, 2009, vol. 39, # 1, p. 158 - 165
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2009, vol. 184, # 7, p. 1843 - 1853
[5] Letters in Organic Chemistry, 2009, vol. 6, # 2, p. 159 - 164
[6] Journal of Fluorine Chemistry, 1988, vol. 38, p. 153 - 162
[7] Journal of Physical Organic Chemistry, 2013, vol. 26, # 8, p. 688 - 695
[8] Organic Letters, 2012, vol. 14, # 8, p. 2066 - 2069
[9] Chemistry - A European Journal, 2013, vol. 19, # 33, p. 10845 - 10848
[10] Tetrahedron, 2014, vol. 70, # 2, p. 312 - 317
  • 4
  • [ 823-85-8 ]
  • [ 107-87-9 ]
  • [ 526-47-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3906 - 3909
  • 5
  • [ 823-85-8 ]
  • [ 399-76-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
  • 6
  • [ 617-35-6 ]
  • [ 823-85-8 ]
  • [ 348-36-7 ]
Reference: [1] Synthetic Communications, 2009, vol. 39, # 14, p. 2506 - 2515
  • 7
  • [ 823-85-8 ]
  • [ 348-36-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
[2] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 8
  • [ 823-85-8 ]
  • [ 123-06-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
86% With sodium ethanolate; sodium hydride In ethanol at 20℃; for 2 h; Heating / reflux Sodium hydride as a 60percent 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, 86percent). LCMS: [M+H]+=203, Rt = 1.02 min, 100percent purity.
46% With triethylamine In ethanol at 50℃; for 2 h; 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 (46percent 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)+.
Reference: [1] European Journal of Organic Chemistry, 2008, # 19, p. 3377 - 3381
[2] Patent: EP1746099, 2007, A1, . Location in patent: Page/Page column 14
[3] Patent: WO2009/68617, 2009, A1, . Location in patent: Page/Page column 58-59
[4] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 6, p. 1425 - 1428
[5] Chinese Chemical Letters, 2017, vol. 28, # 2, p. 377 - 382
  • 9
  • [ 672-81-1 ]
  • [ 823-85-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In ethanol for 16 h; 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, 60percent). ECMS: (ESI) mlz 203 [M+H].
Reference: [1] Patent: US2016/185785, 2016, A1, . Location in patent: Paragraph 2046; 2047
  • 10
  • [ 86240-43-9 ]
  • [ 823-85-8 ]
  • [ 51516-70-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 81 - 87
[2] Drug Development Research, 2018,
  • 11
  • [ 1191-99-7 ]
  • [ 823-85-8 ]
  • [ 101349-12-6 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With ammonium chloride In 2-methyltetrahydrofuran; water at 70℃; for 1 h; Inert atmosphere
Stage #2: at 70℃; Inert atmosphere
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 (98percent) in about 65 percent yield.
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3943 - 3958
[2] Tetrahedron Letters, 2008, vol. 49, # 20, p. 3335 - 3340
[3] Patent: WO2015/128088, 2015, A1, . Location in patent: Page/Page column 19
[4] Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2062 - 2071
[5] Archiv der Pharmazie, 2014, vol. 347, # 1, p. 32 - 41
[6] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6710 - 6717
  • 12
  • [ 371-40-4 ]
  • [ 823-85-8 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogenchloride In water at 20℃; for 2 h;
Stage #2: With sodium nitrite In water at 5℃; for 1 h;
General procedure: A solution of 4-chloroaniline (127.6 g, 1 mol) in concentrated hydrochloric acid (293 mL) was stirred for 2 h at room temperature. To a solution of sodium nitrite (72.5 g, 1.05 mol) in water (145 mL) was added dropwise below 5 °C. After stirring 1 h, filtrate was separated by filtration, to which a solution of NaHSO3 (213.2 g, 2.05 mol) in water (500 mL) was added dropwise at 010 °C and pH was kept between 6 to 7 using 25percent NaOH solution. The resulted mixture was heated to 80 °C for 1 h. Upon cooling to room temperature, concentrated hydrochloric acid (600 mL) was added dropwise and then the mixture was heated to 90-100 °C for 1 h. The mixture was cooled to 10 °C and the precipitate was collected by filtration. 1a was obtained as a light red solid (129.3 g, 60percent).
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
[2] Archiv der Pharmazie (Weinheim, Germany), 1994, vol. 327, # 2, p. 99 - 104
[3] Die Pharmazie, 1985, vol. 40, # 1, p. 21 - 22
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4692 - 4696
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 50, p. 9769 - 9772
[6] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1706 - 1712
[7] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[8] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
[9] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 2, p. 381 - 390
[10] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2314 - 2320
[11] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[12] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[13] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[14] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 761 - 766
[15] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
[16] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 445 - 450
[17] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 529 - 532
[18] Journal of the Chinese Chemical Society, 2018, vol. 65, # 5, p. 538 - 547
[19] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 137 - 147
  • 13
  • [ 460-00-4 ]
  • [ 823-85-8 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; cetyltrimethylammonim bromide; copper(I) bromide In water at 110℃; for 0.166667 h; Sealed tube; Inert atmosphere
Stage #2: With hydrazine hydrate In water at 110℃; for 1 h; Sealed tube; Inert atmosphere
Stage #3: With hydrogenchloride In dichloromethane; water
General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol percent), L3 (110 mg, 0.4 mmol,4 mol percent), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol,3 mol percent) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110° C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110° C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37percent) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol percent of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
[2] Tetrahedron, 2014, vol. 70, # 26, p. 4043 - 4048
[3] RSC Advances, 2014, vol. 4, # 7, p. 3364 - 3367
  • 14
  • [ 371-14-2 ]
  • [ 823-85-8 ]
YieldReaction ConditionsOperation in experiment
39.3% With hydrogenchloride In water at 65℃; (4) salt A mixture of 22. 4 g of 4-fluorophenylhydrazine was dissolved in 15.6 ml of 37percent hydrochloric acid and stirred at 65 ° C until the reaction solution was crystallized. The mixture was cooled to 20 ° C, filtered, and the filter cake was washed with acetone. That is 4-fluorophenylhydrazine hydrochloride finished product 24. 6g, content of 99. 1percent, the yield of 39. 3percent
Reference: [1] Patent: CN106518711, 2017, A, . Location in patent: Paragraph 0017; 0025; 0026
[2] Die Pharmazie, 1985, vol. 40, # 1, p. 21 - 22
  • 15
  • [ 5352-95-4 ]
  • [ 823-85-8 ]
Reference: [1] Journal of the Chinese Chemical Society, 2000, vol. 47, # 1, p. 227 - 240
  • 16
  • [ 823-85-8 ]
  • [ 187949-90-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 81 - 87
[2] Patent: WO2007/144327, 2007, A2,
  • 17
  • [ 823-85-8 ]
  • [ 94-05-3 ]
  • [ 138907-68-3 ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In ethanol for 2.5 h; 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 percent 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 8 h; 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 percent). 1H NMR (300 MHz, CDCl3): δ=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+].
Reference: [1] Patent: WO2008/53136, 2008, A1, . Location in patent: Page/Page column 35-36
[2] Tetrahedron, 2017, vol. 73, # 40, p. 5959 - 5973
[3] Patent: WO2008/74814, 2008, A1, . Location in patent: Page/Page column 55
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4724 - 4728
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 5, p. 1680 - 1684
[6] Patent: WO2008/777, 2008, A2, . Location in patent: Page/Page column 58
[7] Patent: WO2007/144327, 2007, A2, . Location in patent: Page/Page column 70
[8] Patent: WO2008/138876, 2008, A1, . Location in patent: Page/Page column 103-104
  • 18
  • [ 42466-67-1 ]
  • [ 823-85-8 ]
  • [ 138907-68-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 855 - 866
[2] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 81 - 87
  • 19
  • [ 823-85-8 ]
  • [ 946505-09-5 ]
Reference: [1] Patent: WO2007/146824, 2007, A2,
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