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[ CAS No. 79544-29-9 ] {[proInfo.proName]}

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Chemical Structure| 79544-29-9
Chemical Structure| 79544-29-9
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Product Details of [ 79544-29-9 ]

CAS No. :79544-29-9 MDL No. :MFCD00015478
Formula : C7H3FIN Boiling Point : -
Linear Structure Formula :- InChI Key :FAACTMVXBNSPJA-UHFFFAOYSA-N
M.W : 247.01 Pubchem ID :522722
Synonyms :

Calculated chemistry of [ 79544-29-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.83
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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.118 mg/ml ; 0.000477 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.727 mg/ml ; 0.00295 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0473 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 79544-29-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 79544-29-9 ]

* 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 [ 79544-29-9 ]
  • Downstream synthetic route of [ 79544-29-9 ]

[ 79544-29-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 79544-29-9 ]
  • [ 133116-83-3 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2689 - 2697
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  • [ 77326-36-4 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1173 - 1177
[2] Journal of Chemical Sciences, 2013, vol. 125, # 1, p. 71 - 83
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  • [ 1897-52-5 ]
  • [ 79544-29-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1173 - 1177
  • 4
  • [ 79544-29-9 ]
  • [ 146137-72-6 ]
Reference: [1] Patent: US6340759, 2002, B1, . Location in patent: Example 233
  • 5
  • [ 79544-29-9 ]
  • [ 599191-73-8 ]
YieldReaction ConditionsOperation in experiment
96% With hydrazine hydrate In butan-1-ol at 110℃; for 6 h; 500 mg of 2-fluoro-6-iodobenzonitrile and 1.3 ml of hydrazine hydrate (85percent) were dissloved in 10 ml of nbutanoland heated to 110 °C. The mixture was stirred for 6 hours and then cooled to room temperature. Water andethyl acetate were added to separate. The aqueous phase was extracted with ethyl acetate. The combined organicphases was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated todryness to give 502 mg of 4-iodo-1H-indazol-3-amine as tan solid. Yield: 96percent.1H NMR (300 MHz, DMSO-d6) δ (ppm): 5.05 (s, 2H), 6.90-6.96 (m, 1H), 7.29 (d, J = 8.1 Hz, 1H), 7.34 (d, J = 7.5 Hz,1H), 11.80 (s, 1H).
92%
Stage #1: With sodium hydrogencarbonate; hydrazine hydrate In ethanol for 8 h; Reflux
Stage #2: With water In ethanol at 20℃; for 2 h;
2-Fluoro-6-iodobenzonitrile (5 g, 10.1 mmol), NaHCO3 (2.6 g, 31 mmol) and hydrazine monohydrate (5 g, 99.9 mmol) were dissolved in ethanol 60 mL.The resulting mixture was heated to reflux and stirred for 8 h. After cooling to room temperature, 50 ml water was added and the reaction mixture was allowed to stir for another 2 h at room temperature. The product was collected by filtration and dried under vacuum to give 4-Iodo-1H-indazol-3-amine as slight yellow solid (4.8 g, 92percent).
83% With sodium hydrogencarbonate; hydrazine hydrate In ethanol; water for 8 h; Reflux 2-Fluoro-6-iodobenzonitrile (7) (10.0 g, 40 mmol) and NaHCO3(5.2 g, 62 mmol) were suspended in ethanol (60 mL). Aqueoushydrazine monohydrate (12.5 mL) was added onto the above solution.The resulting mixture was heated to reflux and stirred for8 h. After cooling to room temperature,water (60 mL) was added tothe reaction mixture and stirred for another 2 h. The reactionmixture was filtered off and washed with water to give (8) (8.6 g,83percent) as slight yellow solid. mp.: 150e152 C.
77% With sodium hydrogencarbonate; hydrazine hydrate In ethanol at 90℃; for 5 h; 10 g of 2-fluoro-6-iodobenzonitrile was dissolved in 70 mL of absolute ethanol,12.5 mL of hydrazine hydrate and 5.2 g of NaHC03 were added,90 ° C reflux reaction 5h,After completion of the reaction, the reaction solution was cooled to room temperature, Add 120mL of water, a large number of solid precipitation, stirring at room temperature 2h, filtration, the resulting cake is 4-iodo-1H-indazol-3-amine 8g, yield 77percent;
77% With hydrazine hydrate; sodium hydrogencarbonate In ethanol at 90℃; for 5 h; 10 g of 2-fluoro-6-iodobenzonitrile was dissolved in 70 mL of absolute ethanol and 12.5 mL of hydrazine hydrate and 5.2 g of NaHCO3 were added thereto. The mixture was refluxed for 5 hours at 90 ° C. After the completion of the reaction, the reaction solution was cooled to room temperature, , A large number of solid precipitation, stirring at room temperature 2h, filtration, the resulting filter cake is 4-iodine-1 H-indazole-3-amine, about 8g, yield 77percent;
77% With sodium hydrogencarbonate; hydrazine hydrate In ethanol for 8 h; Reflux 2-Fluoro-6-iodobenzonitrile was dissolved in ethanol (70 mL),then hydrazine hydrate (12.5 mL), NaHCO3 (5.2 g) was added. Theresulting mixture was heated to reflux and stirred for 8 h. Aftercooling to room temperature, 50 mL water was added and the reactionmixture was allowed to stir for another 2 h at room temperature.The product was collected by filtration and dried undervacuum to afford 4-iodine -1H-indazol-3-ylamine (2) as slightyellow solid (8 g, 77percent).
77% With hydrazine hydrate In ethanol for 8 h; Reflux; Alkaline conditions 2-Fluoro-6-iodobenzonitrile 1 (10.0g, 40mmol) and Na2CO3(5.2g, 62mmol) were suspended in ethanol (70mL), hydrazine hydrate (12.5mL) was added. The resulting mixture was heated to reflux and stirred for 8h. After cooling to r.m., 50mL water was added and the reaction mixture was allowed to stir for another 2hat r.m. and 2hat 0°C. The product was collected by filtration, washed with water and dried under vacuum to give 4-iodine-1H-indazol-3-ylamine 2 as yellow solid (8.0g, 77percent).
1.4 g With hydrazine hydrate In butan-1-ol at 110℃; for 5 h; To a mixture of 2-Fluoro-6-iodibenzonitrile (2 g, 8.1mmol) in 40 ml of n-butanol was added hydrazine monohydrate (4 ml). The reaction was equipped with a reflux condenser and stirred at 1100 C. for 5 hours. Next, the reactionwas cooled to room temperature, poured into water andextracted with ethyl acetate. The ethyl acetate layer waswashed with brine, dried using anhydrous sodium sulfate, andconcentrated to give 1.4 g of 4-iodo-1H-indazol-3-amine.

Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[2] Patent: EP3112351, 2017, A1, . Location in patent: Paragraph 0029
[3] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1419 - 1425
[4] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 139 - 147
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1584 - 1597
[6] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 80 - 90
[7] Patent: CN105924385, 2016, A, . Location in patent: Paragraph 0096-0099
[8] Patent: CN105906568, 2016, A, . Location in patent: Paragraph 0035; 0036
[9] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 275 - 285
[10] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 373 - 385
[11] Patent: US2004/235892, 2004, A1, . Location in patent: Page 15
[12] Patent: EP1932831, 2008, A1, . Location in patent: Page/Page column 48
[13] Patent: WO2008/86014, 2008, A2, . Location in patent: Page/Page column 58-59
[14] Patent: US2004/14802, 2004, A1, . Location in patent: Page/Page column 21
[15] Patent: US9233968, 2016, B1, . Location in patent: Page/Page column 54
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  • [ 796967-16-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1584 - 1597
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