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Product Details of [ 3939-09-1 ]

CAS No. :3939-09-1 MDL No. :MFCD00009826
Formula : C7H3F2N Boiling Point : -
Linear Structure Formula :- InChI Key :LJFDXXUKKMEQKE-UHFFFAOYSA-N
M.W : 139.10 Pubchem ID :77545
Synonyms :

Calculated chemistry of [ 3939-09-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 31.07
TPSA : 23.79 Ų

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) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.68
Log Po/w (MLOGP) : 2.32
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.445 mg/ml ; 0.0032 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 0.745 mg/ml ; 0.00535 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.135 mg/ml ; 0.000971 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 3939-09-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3939-09-1 ]

* 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 [ 3939-09-1 ]
  • Downstream synthetic route of [ 3939-09-1 ]

[ 3939-09-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 85118-02-1 ]
  • [ 3939-09-1 ]
YieldReaction ConditionsOperation in experiment
83.4% With trichlorophosphate In N,N-dimethyl-formamide at -15 - 20℃; for 7.5 h; In a 250 mL three-necked flask, 2,4-difluorobenzamide was added(23.0 g, 146.2 mmol) was dissolved in dry formN, N-dimethylformamide (80 mL), cooled to -15 ° C,Phosphorus oxychloride (112. lg, 730.9 mmol) was slowly added dropwise,Incubation reaction 0.5h, room temperature reaction 7h. Reaction is completed,The reaction solution slowly into the ice that is solid precipitation,And 17.0 g of 2,4-difluorobenzonitrile was taken in a yield of 83.4percent.
Reference: [1] Patent: CN106854165, 2017, A, . Location in patent: Paragraph 0104; 0105; 0136; 0137
  • 2
  • [ 1435-44-5 ]
  • [ 557-21-1 ]
  • [ 3939-09-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 9, p. 1711 - 1714
[2] Tetrahedron Letters, 2010, vol. 51, # 37, p. 4833 - 4836
  • 3
  • [ 1435-44-5 ]
  • [ 151-50-8 ]
  • [ 3939-09-1 ]
Reference: [1] Chemistry - A European Journal, 2003, vol. 9, # 8, p. 1828 - 1836
  • 4
  • [ 773837-37-9 ]
  • [ 2265-93-2 ]
  • [ 3939-09-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2345 - 2351
  • 5
  • [ 28163-00-0 ]
  • [ 3939-09-1 ]
  • [ 60702-69-4 ]
Reference: [1] Journal of Fluorine Chemistry, 1993, vol. 63, # 1-2, p. 25 - 30
  • 6
  • [ 4110-33-2 ]
  • [ 3939-09-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1993, # 11, p. 921 - 922
  • 7
  • [ 4110-33-2 ]
  • [ 3939-09-1 ]
  • [ 34667-88-4 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1993, # 11, p. 921 - 922
  • 8
  • [ 367-25-9 ]
  • [ 3939-09-1 ]
Reference: [1] Archiv der Pharmazie, 2017, vol. 350, # 2,
  • 9
  • [ 1583-58-0 ]
  • [ 3939-09-1 ]
Reference: [1] Patent: CN106854165, 2017, A,
  • 10
  • [ 72482-64-5 ]
  • [ 3939-09-1 ]
Reference: [1] Patent: CN106854165, 2017, A,
  • 11
  • [ 4110-33-2 ]
  • [ 3939-09-1 ]
  • [ 34667-88-4 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1993, # 11, p. 921 - 922
  • 12
  • [ 3939-09-1 ]
  • [ 865-33-8 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 13
  • [ 3939-09-1 ]
  • [ 72235-52-0 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 14, p. 4437 - 4440
  • 14
  • [ 3939-09-1 ]
  • [ 82380-18-5 ]
Reference: [1] Patent: CN108774155, 2018, A, . Location in patent: Paragraph 0030-0037
  • 15
  • [ 3939-09-1 ]
  • [ 80517-22-2 ]
  • [ 53312-80-4 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 140℃; for 0.666667 h;
Stage #2: at 20℃;
2,4-Difluorobenzonitrile (2.78 g, 20 mmol) and 3,4,5-trimethoxybenzylamine (3.94 g, 20 mmol) are combined and heated at 140 C for 40 m.
The mixture is allowed to cool to RT and is then dissolved in TFA (20 mL) and stirred at RT overnight.
The mixture is then concentrated on the rotavap and partitioned between 1N NaOH (enough till basic, ~100 mL) and ethyl acetate (100 mL).
The organic layer is removed and the aqueous layer is extracted with more ethyl acetate (100 mL).
The combined layers are washed with brine (50 mL), dried (MgSO4) and concentrated to an oil.
The mixture is chromatographed (10 to 40percent, EtOAc in hexanes) giving the isomers as two well separated products.
The later eluding product is concentrated to give 4-Amino-2-fluoro-benzonitrile (1.07 g, 39percent) as a white solid. (LC/MS m/z=177.8 for M+H+acetonitrile)
Reference: [1] Patent: US2008/76813, 2008, A1, . Location in patent: Page/Page column 28
  • 16
  • [ 28163-00-0 ]
  • [ 3939-09-1 ]
  • [ 60702-69-4 ]
Reference: [1] Journal of Fluorine Chemistry, 1993, vol. 63, # 1-2, p. 25 - 30
  • 17
  • [ 3939-09-1 ]
  • [ 80517-22-2 ]
  • [ 53312-80-4 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 140℃; for 0.666667 h;
Stage #2: at 20℃;
2,4-Difluorobenzonitrile (2.78 g, 20 mmol) and 3,4,5-trimethoxybenzylamine (3.94 g, 20 mmol) are combined and heated at 140 C for 40 m.
The mixture is allowed to cool to RT and is then dissolved in TFA (20 mL) and stirred at RT overnight.
The mixture is then concentrated on the rotavap and partitioned between 1N NaOH (enough till basic, ~100 mL) and ethyl acetate (100 mL).
The organic layer is removed and the aqueous layer is extracted with more ethyl acetate (100 mL).
The combined layers are washed with brine (50 mL), dried (MgSO4) and concentrated to an oil.
The mixture is chromatographed (10 to 40percent, EtOAc in hexanes) giving the isomers as two well separated products.
The later eluding product is concentrated to give 4-Amino-2-fluoro-benzonitrile (1.07 g, 39percent) as a white solid. (LC/MS m/z=177.8 for M+H+acetonitrile)
Reference: [1] Patent: US2008/76813, 2008, A1, . Location in patent: Page/Page column 28
  • 18
  • [ 3939-09-1 ]
  • [ 67152-20-9 ]
YieldReaction ConditionsOperation in experiment
95% at 0℃; for 4 h; Potassium nitrate (16.4 g, 147.4 mmol) was added to concentrated H2SO4 (85 ml, 1582 mmol) at 0 °C, followed by slow addition of 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol).The suspension was stirred at this temperature for an additional 4 hrs and quenched ice / water (800 ml). The resulting solid was collected by filtration and dried to give the title compound (13.8 g, 95percent) as a white solid. NMR (400 MHz, CDCl3) 8.48 (m, IH), 7.24 (m, IH).
95% With sulfuric acid; potassium nitrate In water at 0℃; for 4 h; Potassium nitrate (16.4 g, 147.4 mmol) was added to concentrated H2S04 (85 ml, 1582 mmol) at 0 °C, followed by slow addition of 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol). The suspension was stirred at this temperature for an additional 4 hrs and quenched ice/ water (800 ml). The resulting solid was collected by filtration and dried to give the title compound (13.8 g, 95percent) as a white solid. NMR (400 MHz, CDC13) 8.48 (m, 1H), 7.24 (m, 1H).
88.4% at -10 - 20℃; for 1.5 h; In 251 ^ three bottles, 2,4-difluorobenzonitrile (17.28,123.71111111) dissolved in concentrated sulfuric acid (351 ^), coolingTo -10 ° C, dropping fuming nitric acid (155.9g, 2474.4mmol), incubation reaction 0.5h, room temperature reaction lh. The reaction is finished,The liquid slowly into the ice that is solid precipitation, filtration, filter cake vacuum drying 2,4 - difluoro - 5 - nitrobenzonitrile 20. lg, yieldWas 88.4percent.
Reference: [1] Patent: WO2006/87530, 2006, A1, . Location in patent: Page/Page column 59
[2] Patent: WO2005/103010, 2005, A2, . Location in patent: Page/Page column 40
[3] Patent: CN106854165, 2017, A, . Location in patent: Paragraph 0106; 0107; 0138; 0139
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 4, p. 467 - 475
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 2019 - 2022
  • 19
  • [ 3939-09-1 ]
  • [ 67152-20-9 ]
  • [ 226701-59-3 ]
Reference: [1] Patent: US6150379, 2000, A,
  • 20
  • [ 3939-09-1 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: US2005/20611, 2005, A1, . Location in patent: Page/Page column 39
  • 21
  • [ 3939-09-1 ]
  • [ 865-33-8 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 22
  • [ 3939-09-1 ]
  • [ 404827-75-4 ]
YieldReaction ConditionsOperation in experiment
44.7% With hydrazine hydrate In butan-1-ol at 150℃; for 17 h; Inert atmosphere 2,4-Difluorobenzonitrile (10.00 g, 71.89 mmol) was added into a 500 mL two-neckflask, then n-butanol (200 mL) was added. Then to the mixture was added hydrazine hydrate(70.0 mL, 1443 mmol) under nitrogen protection. After addition, the mixture was heated to150 oc and stirred for 17 hours. After the reaction was completed, the reaction mixture wascooled tort, and extracted with EtOAc (200 mL x 3). The combined organic layers were washedwith water (200 mL x 2) and saturated brine (200 mL ), dried over anhydrous sodium sulfate,filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gelchromatograph (petroleum ether/ethyl acetate (v/v) = 1/2) to give the title compound as yellowliquid (4.85 g, 44.7percent).MS (ESI, pos. ion) m/z: 152.2 (M+ 1).
38% for 5 h; Reflux Step A: 6-Fluoro-1H-indazol-3-amine To 2,4-difluorobenzonitrile (1.21 g, 8.70 mmol) was added hydrazine monohydrate (8.46 mL, 174 mmol). The mixture was heated to reflux for 5 hours and then poured onto ice. The solution was extracted with ethyl acetate, dried with magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (25-100percent ethyl acetate/hexane) to afford 6-fluoro-1H-indazol-3-amine (0.5 g, 3.3 mmol, 38percent yield) as light yellow powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 11.42 (s, 1H), 7.70 (dd, J=8.55, 5.49 Hz, 1H), 6.97 (dd, J=10.07, 1.83 Hz, 1H), 6.72-6.79 (m, 1H), 5.40 (s, 2H). MS (LC/MS) R.T.=0.61; [M+H]+=152.11.
38% for 5 h; Reflux Step A: 6-fluoro-1H-indazol-3-amine
To 2,4-difluorobenzonitrile (1.21 g, 8.70 mmol) was added hydrazine monohydrate (8.46 mL, 174 mmol). The mixture was heated to reflux for 5 hours and then poured onto ice. The solution was extracted with ethyl acetate, dried with magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (25-100percent ethyl acetate/hexane) to afford 6-fluoro-lH-indazol-3- amine (0.5 g, 3.3 mmol, 38 percent yield) as light yellow powder. 3/4 NMR (500 MHz, DMSO-D6) δ ppm 11.42 (s, 1 H), 7.70 (dd, J=8.55, 5.49 Hz, 1 H), 6.97 (dd, J=10.07, 1.83 Hz, 1 H), 6.72 - 6.79 (m, 1 H), 5.40 (s, 2 H). MS (LC/MS) R.T. = 0.61; [M+H]+ = 152.11.
38% for 5 h; Reflux To 2,4-difluorobenzonitrile (1.21 g, 8.70 mmol) wasadded hydrazine monohydrate (8.46 ml., 174 mmol). Themixture was heated to reflux for 5 hours and then poured ontoice. The solution was extracted with ethyl acetate, dried withmagnesium sulfate, filtered and concentrated. The residuewas purified by colunm chromatography (25-100percent ethylacetate/hexane) to afford 6-f1uoro-IH-indazol-3-amine (0.5g, 3.3 mmol, 38percent yield) as light yellow powder.

Reference: [1] Patent: WO2018/188590, 2018, A1, . Location in patent: Paragraph 00316
[2] Patent: US2009/270405, 2009, A1, . Location in patent: Page/Page column 82-83
[3] Patent: WO2011/53292, 2011, A1, . Location in patent: Page/Page column 133
[4] Patent: JP5714745, 2015, B2, . Location in patent: Paragraph 0264; 0265
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