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[ CAS No. 74784-70-6 ] {[proInfo.proName]}

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Chemical Structure| 74784-70-6
Chemical Structure| 74784-70-6
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Product Details of [ 74784-70-6 ]

CAS No. :74784-70-6 MDL No. :MFCD00042164
Formula : C6H5F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RSGVKIIEIXOMPY-UHFFFAOYSA-N
M.W :162.11 Pubchem ID :735862
Synonyms :

Calculated chemistry of [ 74784-70-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.64
TPSA : 38.91 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 2.84
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.14 mg/ml ; 0.00703 mol/l
Class : Soluble
Log S (Ali) : -1.97
Solubility : 1.75 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.465 mg/ml ; 0.00287 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 74784-70-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74784-70-6 ]

* 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 [ 74784-70-6 ]
  • Downstream synthetic route of [ 74784-70-6 ]

[ 74784-70-6 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 50488-42-1 ]
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Reference: [1] Chemical Communications, 2010, vol. 46, # 6, p. 925 - 927
  • 2
  • [ 113495-47-9 ]
  • [ 74784-70-6 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 8, p. 2065 - 2068
  • 3
  • [ 52334-81-3 ]
  • [ 74784-70-6 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
[2] Patent: US5491239, 1996, A,
[3] Tetrahedron Letters, 2013, vol. 54, # 5, p. 414 - 418
[4] Journal of Physical Organic Chemistry, 2013, vol. 26, # 12, p. 1038 - 1043
  • 4
  • [ 52334-81-3 ]
  • [ 4214-73-7 ]
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Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
  • 5
  • [ 22253-72-1 ]
  • [ 74784-70-6 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 8, p. 2065 - 2068
  • 6
  • [ 573676-20-7 ]
  • [ 573675-81-7 ]
  • [ 74784-70-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4573 - 4577
  • 7
  • [ 69045-78-9 ]
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Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
[2] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
  • 8
  • [ 507-40-4 ]
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  • [ 79456-26-1 ]
Reference: [1] Patent: US5491239, 1996, A,
  • 9
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  • [ 79456-26-1 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
  • 10
  • [ 74784-70-6 ]
  • [ 33252-64-1 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
  • 11
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  • [ 72587-15-6 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
  • 12
  • [ 74784-70-6 ]
  • [ 107867-51-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3719 - 3742
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[3] Patent: US2014/315888, 2014, A1,
[4] Patent: EP2865266, 2015, A1,
[5] Patent: US5620978, 1997, A,
  • 13
  • [ 74784-70-6 ]
  • [ 79456-30-7 ]
YieldReaction ConditionsOperation in experiment
96 g With N-Bromosuccinimide In chloroform at 20 - 80℃; for 1.5 h; Cooling with ice Production Example 59-1
71 g of N-bromosuccinimide was added to a mixture of 65 g of 5-trifluoromethyl-pyridine-2-ylamine and 100 mL of chloroform by being divided into 5 portions under ice water-cooling, The temperature was elevated to room temperature and the mixture was stirred for 1 hour.
Then, the mixture was heated to 80°C and was heated and stirred for 3C minutes.
After allowing the mixture to cool to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the mixture, which was then subjected to extraction using chloroform.
A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure.
The residue was subjected to silicagel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine. 3-bromo-5-trifluoromethyl-pyridin-2-ylamine 1H-NMR (CDCl3) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 12, p. 1715 - 1720
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782
[3] Patent: US5861419, 1999, A,
[4] Patent: US6046217, 2000, A,
[5] Patent: US6004950, 1999, A,
[6] Patent: EP1012142, 2004, B1, . Location in patent: Page 27
[7] Patent: EP1015431, 2005, B1, . Location in patent: Page/Page column 23
[8] Patent: EP2865266, 2015, A1, . Location in patent: Paragraph 0676
  • 14
  • [ 79456-29-4 ]
  • [ 74784-70-6 ]
  • [ 79456-30-7 ]
Reference: [1] Patent: US4349681, 1982, A,
  • 15
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  • [ 211308-82-6 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With sulfuric acid; iodine; acetic acid; periodic acid In water at 85℃; for 18 h;
Stage #2: With sodium hydroxide In water at 20℃;
[0183] To 2-amino 5-trifluoromethyl pyridine, (50g, 308mmol) was added acetic acid (50OmL), followed by pre-mixed water (35mL) and concentrated sulfuric acid (5mL) and stirred until completely solubilised. Periodic acid (13.3g, 58mmol) was added followed by iodine (31.2g, 123mmol) and then the reaction mixture was heated to 85 0C for 18 hours. [0184] The reaction mixture was allowed to cool to room temperature and then carefully basified with 4M NaOH solution to pH 10-14. This gave a precipitate which was isolated by filtration and stirred in water (.1 litre), filtered and dried to give the product as a brown powder (61.38g, 69percent).
67% With sulfuric acid; iodine; acetic acid; periodic acid In water at 80℃; for 16 h; Inert atmosphere [0522] To a stirred solution of 5-(trifluoromethyl) pyridin-2-amine (100 g, 617 mmol) in acetic acid (1 Lit) at room temperature under an argon atmosphere were added concentratedsulfuric acid (5 mL), periodic acid (26 g, 123 mmol) and iodine (62 g, 246 mmol). The reaction mixture was stirred at 80 °C for 16 h. After consumption of starting material (by TLC), the reaction mixture was basified with sodium hydroxide solution (200 mL) at 0 °C, to obtain the solid. The solid was filtered and concentrated in vacuo to obtain 3-iodo-5- (trifluoromethyl) pyridin-2-amine (120 g, 67percent) as an off-white solid. ‘H NMR (DMSO-d6 500 MHz): 8.27 (s, 1H), 8.16 (s, 1H), 6.87 (brs, 2H); TLC: 10percent EtOAc Hexane (R1 0.4).
14.3 g With iodine; silver sulfate In ethanol at 10 - 35℃; To a mixture of 5-(trifluoromethyl)pyridin-2-amine (12.0 g), silver(I) sulfate (23.1 g) and ethanol (400 mL) was added iodine (37.6 g) in several parts at room temperature, and the reaction mixture was stirred overnight at room temperature.
To the reaction solution was added saturated aqueous sodium thiosulfate solution, and the mixture was stirred for 30 min, and neutralize with 1N aqueous sodium hydroxide solution.
The insoluble substance was removed by filtration, the filtrate was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (14.3 g).
MS (APCI+): [M+H]+ 289.0
Reference: [1] Patent: WO2008/79346, 2008, A1, . Location in patent: Page/Page column 58
[2] Patent: WO2017/31325, 2017, A1, . Location in patent: Paragraph 0522
[3] Patent: WO2017/133667, 2017, A1, . Location in patent: Page/Page column 116; 117
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1160 - 1170
[5] Patent: US2005/277681, 2005, A1, . Location in patent: Page/Page column 26
[6] Patent: US2008/125459, 2008, A1, . Location in patent: Page/Page column 13-14
[7] Patent: US2009/253679, 2009, A1, . Location in patent: Page/Page column 42
[8] Patent: US2009/298865, 2009, A1, . Location in patent: Page/Page column 7-8
[9] Patent: US2015/266872, 2015, A1, . Location in patent: Paragraph 0795; 0796
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Reference: [1] Patent: WO2017/31325, 2017, A1,
[2] Patent: WO2017/133667, 2017, A1,
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